diff --git a/Loop.xcodeproj/project.pbxproj b/Loop.xcodeproj/project.pbxproj
index 5cc2da5b..b9fb0106 100644
--- a/Loop.xcodeproj/project.pbxproj
+++ b/Loop.xcodeproj/project.pbxproj
@@ -95,7 +95,6 @@
 			buildConfigurationList = A8E59C44297F5E9B0064D4BA /* Build configuration list for PBXNativeTarget "Loop" */;
 			buildPhases = (
 				A8E59C31297F5E9A0064D4BA /* Sources */,
-				A80FD0D82CB34BA300DCC00B /* Run SwiftFormat */,
 				A8E59C32297F5E9A0064D4BA /* Frameworks */,
 				A8E59C33297F5E9A0064D4BA /* Resources */,
 			);
@@ -175,28 +174,6 @@
 		};
 /* End PBXResourcesBuildPhase section */
 
-/* Begin PBXShellScriptBuildPhase section */
-		A80FD0D82CB34BA300DCC00B /* Run SwiftFormat */ = {
-			isa = PBXShellScriptBuildPhase;
-			alwaysOutOfDate = 1;
-			buildActionMask = 2147483647;
-			files = (
-			);
-			inputFileListPaths = (
-			);
-			inputPaths = (
-			);
-			name = "Run SwiftFormat";
-			outputFileListPaths = (
-			);
-			outputPaths = (
-			);
-			runOnlyForDeploymentPostprocessing = 0;
-			shellPath = /bin/sh;
-			shellScript = "# Default Homebrew installation path on Intel-based Macs\nHOMEBREW_INTEL_PATH=\"/usr/local/bin/swiftformat\"\n\n# Default Homebrew installation path on Apple Silicon Macs\nHOMEBREW_ARM_PATH=\"/opt/homebrew/bin/swiftformat\"\n\n# Determine the architecture of the machine (arm64 or x86_64)\nARCH=$(uname -m)\n\n# Set the Homebrew path based on the architecture\nif [ \"$ARCH\" = \"arm64\" ]; then\n    SWIFTFORMAT_PATH=\"$HOMEBREW_ARM_PATH\"\nelse\n    SWIFTFORMAT_PATH=\"$HOMEBREW_INTEL_PATH\"\nfi\n\n# Check if SwiftFormat is installed via Homebrew\nif [ -x \"$SWIFTFORMAT_PATH\" ]; then\n    \"$SWIFTFORMAT_PATH\" .\nelse\n    echo \"warning: SwiftFormat not installed via Homebrew or not found in expected paths\"\nfi\n";
-		};
-/* End PBXShellScriptBuildPhase section */
-
 /* Begin PBXSourcesBuildPhase section */
 		A8E59C31297F5E9A0064D4BA /* Sources */ = {
 			isa = PBXSourcesBuildPhase;
diff --git a/Loop/App/DataPatcher.swift b/Loop/App/DataPatcher.swift
index 4b73c6d8..5fb6f1bd 100644
--- a/Loop/App/DataPatcher.swift
+++ b/Loop/App/DataPatcher.swift
@@ -11,9 +11,9 @@ import Scribe
 
 enum DataPatcher {
     static func run() {
-        let initialPatches = Defaults[.patchesApplied]
+        let initialPatches: Patches = Defaults[.patchesApplied]
 
-        if !initialPatches.contains(.accentColorMode) {
+        runPatch(patch: .changeToAccentColorMode, initial: initialPatches) {
             // Migrate to accent color mode
             // We need to migrate `useSystemAccentColor` and `processWallpaper` over to `accentColorMode`
             let useSystemAccentColor: Bool = Defaults[.useSystemAccentColor]
@@ -27,14 +27,28 @@ enum DataPatcher {
                 Defaults[.accentColorMode] = .custom
             }
 
-            Defaults[.patchesApplied].formUnion(.accentColorMode)
-            Log.info("Ran patch accentColorMode", category: .dataPatcher)
+            Defaults.reset(.useSystemAccentColor)
+            Defaults.reset(.processWallpaper)
+        }
+
+        runPatch(patch: .removeRevealedStashedWindows, initial: initialPatches) {
+            Defaults.reset(.stashManagerRevealedWindows)
+        }
+    }
+
+    private static func runPatch(patch: Patches, initial: Patches, with callback: () -> ()) {
+        if !initial.contains(patch) {
+            callback()
+
+            Defaults[.patchesApplied].formUnion(patch)
+            Log.info("Ran patch \(patch)", category: .dataPatcher)
         }
     }
 
-    struct Patch: OptionSet, Defaults.Serializable {
+    struct Patches: OptionSet, Defaults.Serializable {
         let rawValue: Int
 
-        static let accentColorMode = Self(rawValue: 1 << 0)
+        static let changeToAccentColorMode = Self(rawValue: 1 << 0)
+        static let removeRevealedStashedWindows = Self(rawValue: 1 << 1)
     }
 }
diff --git a/Loop/Core/LoopManager.swift b/Loop/Core/LoopManager.swift
index b1ab8285..26c06cd9 100644
--- a/Loop/Core/LoopManager.swift
+++ b/Loop/Core/LoopManager.swift
@@ -84,7 +84,7 @@ final class LoopManager: ObservableObject {
 // MARK: - Opening/Closing Loop
 
 extension LoopManager {
-    private func openLoop(startingAction: WindowAction?) {
+    private func openLoop(startingAction: WindowAction) {
         guard AccessibilityManager.shared.isGranted else {
             return
         }
@@ -96,9 +96,7 @@ extension LoopManager {
             /// In these cases, we can simply update the action instead of reopening the Loop.
             /// Enabling keybindObserver was considered as a workaround, but it doesn't start quickly enough.
             /// Although Karabiner-Elements sends key events separately, they arrive in quick succession.
-            if let startingAction {
-                changeAction(startingAction, disableHapticFeedback: true)
-            }
+            changeAction(startingAction, disableHapticFeedback: true)
             return
         }
 
@@ -111,7 +109,7 @@ extension LoopManager {
             return
         }
 
-        Log.info("Opening Loop with starting action: \(startingAction?.description ?? "(none)") and target window: \(window?.description ?? "(none)")", category: .loopManager)
+        Log.info("Opening Loop with starting action: \(startingAction.description) and target window: \(window?.description ?? "(none)")", category: .loopManager)
 
         // Record the first frame in advance if the preview window is disabled
         if let window,
@@ -152,10 +150,7 @@ extension LoopManager {
         }
 
         isLoopActive = true
-
-        if let startingAction {
-            changeAction(startingAction, disableHapticFeedback: true)
-        }
+        changeAction(startingAction, disableHapticFeedback: true)
     }
 
     private func closeLoop(forceClose: Bool) {
@@ -196,7 +191,7 @@ extension LoopManager {
         LoopManager.lastTargetFrame = .zero
     }
 
-    private func openWindows(startingAction: WindowAction?, window: Window?) {
+    private func openWindows(startingAction: WindowAction, window: Window?) {
         if Defaults[.previewVisibility], let screenToResizeOn {
             previewController.open(
                 screen: screenToResizeOn,
@@ -236,7 +231,7 @@ extension LoopManager {
         canAdvanceCycle: Bool = true
     ) {
         guard
-            !currentAction.isSameManipulation(as: newAction) || newAction.shouldImmediatelyExecuteAction,
+            currentAction.id != newAction.id || newAction.shouldImmediatelyExecuteAction,
             isLoopActive,
             let currentScreen = screenToResizeOn
         else {
diff --git a/Loop/Core/Observers/Helpers/DoubleClickTimer.swift b/Loop/Core/Observers/Helpers/DoubleClickTimer.swift
index ce029392..12edd70b 100644
--- a/Loop/Core/Observers/Helpers/DoubleClickTimer.swift
+++ b/Loop/Core/Observers/Helpers/DoubleClickTimer.swift
@@ -14,18 +14,18 @@ import Defaults
 /// two occur within the system-defined (and user-customizable) `NSEvent.doubleClickInterval`.
 final class DoubleClickTimer {
     private var lastTriggerKeyPressTime: Date?
-    private let openCallback: (WindowAction?) -> ()
+    private let openCallback: (WindowAction) -> ()
     private var doubleClickInterval: TimeInterval { NSEvent.doubleClickInterval }
 
     /// Creates a new `DoubleClickTimer` instance with the specified callback to invoke on a double-press event.
     /// - Parameter openCallback: A closure that is called when a double-click is detected. The closure receives the `WindowAction` associated with the trigger as its parameter.
-    init(openCallback: @escaping (WindowAction?) -> ()) {
+    init(openCallback: @escaping (WindowAction) -> ()) {
         self.openCallback = openCallback
     }
 
     /// Handles a trigger event (such as a key press) and determines whether it qualifies as a "double-click".
     /// - Parameter startingAction: The `WindowAction` associated with the trigger.
-    func handleTrigger(startingAction: WindowAction?) {
+    func handleTrigger(startingAction: WindowAction) {
         let now = Date()
 
         // If we detect a double-press, trigger immediately. Otherwise, just record the time
diff --git a/Loop/Core/Observers/Helpers/TriggerDelayTimer.swift b/Loop/Core/Observers/Helpers/TriggerDelayTimer.swift
index 2ab8e70c..3c662bf3 100644
--- a/Loop/Core/Observers/Helpers/TriggerDelayTimer.swift
+++ b/Loop/Core/Observers/Helpers/TriggerDelayTimer.swift
@@ -16,8 +16,8 @@ import Foundation
 /// In that case, use the `updateStartingAction` method.
 final class TriggerDelayTimer {
     private var triggerDelayTimer: Task<(), Never>?
-    private var startingAction: WindowAction?
-    private let openCallback: (WindowAction?) -> ()
+    private var startingAction: WindowAction = .init(.noSelection)
+    private let openCallback: (WindowAction) -> ()
     private var triggerDelay: CGFloat { Defaults[.triggerDelay] }
 
     /// Indicates whether the delay timer is currently active.
@@ -25,7 +25,7 @@ final class TriggerDelayTimer {
 
     /// Creates a new `TriggerDelayTimer` instance with the specified callback to invoke after a user-configured delay has elapsed.
     /// - Parameter openCallback: A closure that is called once the trigger delay completes successfully. The closure receives the latest `WindowAction` depending on what has been set.
-    init(openCallback: @escaping (WindowAction?) -> ()) {
+    init(openCallback: @escaping (WindowAction) -> ()) {
         self.openCallback = openCallback
     }
 
@@ -38,7 +38,7 @@ final class TriggerDelayTimer {
     /// If another trigger is received before the delay elapses, the previous timer is canceled and restarted.
     /// Once the configured delay duration passes without interruption, the provided callback is invoked, with the latest inputted starting action.
     /// - Parameter startingAction: The `WindowAction` associated with the trigger.
-    func handleTrigger(startingAction action: WindowAction?) {
+    func handleTrigger(startingAction action: WindowAction) {
         startingAction = action
         cancel() // Ensure no previous timer is active
 
@@ -53,7 +53,7 @@ final class TriggerDelayTimer {
 
     /// Updates the stored `startingAction` value without restarting the timer. To be used with keybinds.
     /// - Parameter newAction: The new `WindowAction` to associate with the current trigger delay.
-    func updateStartingAction(with newAction: WindowAction?) {
+    func updateStartingAction(with newAction: WindowAction) {
         startingAction = newAction
     }
 
@@ -61,6 +61,6 @@ final class TriggerDelayTimer {
     func cancel() {
         triggerDelayTimer?.cancel()
         triggerDelayTimer = nil
-        startingAction = nil
+        startingAction = .init(.noSelection)
     }
 }
diff --git a/Loop/Core/Observers/KeybindTrigger.swift b/Loop/Core/Observers/KeybindTrigger.swift
index 893137f0..0c28b552 100644
--- a/Loop/Core/Observers/KeybindTrigger.swift
+++ b/Loop/Core/Observers/KeybindTrigger.swift
@@ -13,7 +13,7 @@ import Defaults
 final class KeybindTrigger {
     // Parameters
     private let windowActionCache: WindowActionCache
-    private let openCallback: (WindowAction?) -> ()
+    private let openCallback: (WindowAction) -> ()
     private let closeCallback: (Bool) -> ()
     private let checkIfLoopOpen: () -> Bool
 
@@ -58,7 +58,7 @@ final class KeybindTrigger {
     ///   - closeCallback: what to do when the trigger key is released, and Loop should be closed.
     init(
         windowActionCache: WindowActionCache,
-        openCallback: @escaping (WindowAction?) -> (),
+        openCallback: @escaping (WindowAction) -> (),
         closeCallback: @escaping (Bool) -> (),
         checkIfLoopOpen: @escaping () -> Bool
     ) {
@@ -193,7 +193,10 @@ final class KeybindTrigger {
 
                 // Only trigger Loop without an action if the only pressed keys perfectly matches the trigger key.
                 if allPressedKeys == triggerKey {
-                    openLoop(startingAction: nil, overrideExistingTriggerDelayTimerAction: !isARepeat)
+                    openLoop(
+                        startingAction: .init(.noSelection),
+                        overrideExistingTriggerDelayTimerAction: !isARepeat
+                    )
                     return .opening
                 }
             } else {
@@ -205,7 +208,7 @@ final class KeybindTrigger {
         return .forward
     }
 
-    private func openLoop(startingAction: WindowAction?, overrideExistingTriggerDelayTimerAction: Bool) {
+    private func openLoop(startingAction: WindowAction, overrideExistingTriggerDelayTimerAction: Bool) {
         if checkIfLoopOpen() {
             openCallback(startingAction) // Only update Loop to the latest WindowAction
         } else {
@@ -230,7 +233,7 @@ final class KeybindTrigger {
     }
 
     private func startTriggerDelayTimer(
-        startingAction: WindowAction?,
+        startingAction: WindowAction,
         overrideExistingTriggerDelayTimerAction: Bool
     ) {
         // If a trigger delay timer is already active, only update its startingAction when
diff --git a/Loop/Core/Observers/MiddleClickTrigger.swift b/Loop/Core/Observers/MiddleClickTrigger.swift
index a4c6a6cb..a185763c 100644
--- a/Loop/Core/Observers/MiddleClickTrigger.swift
+++ b/Loop/Core/Observers/MiddleClickTrigger.swift
@@ -11,7 +11,7 @@ import Defaults
 /// Reads middle-click events using a PassiveEventMonitor, and triggers Loop open/close callbacks, when appropriate.
 final class MiddleClickTrigger {
     // Callbacks
-    private let openCallback: (WindowAction?) -> ()
+    private let openCallback: (WindowAction) -> ()
     private let closeCallback: (Bool) -> ()
 
     // State-tracking
@@ -27,7 +27,7 @@ final class MiddleClickTrigger {
         guard let self else { return }
 
         if useTriggerDelay {
-            triggerDelayTimer.handleTrigger(startingAction: nil)
+            triggerDelayTimer.handleTrigger(startingAction: .init(.noSelection))
         } else {
             openCallback(action)
         }
@@ -38,7 +38,7 @@ final class MiddleClickTrigger {
     ///   - openCallback: what to do when the middle mouse button is pressed, and Loop should be activated.
     ///   - closeCallback: what to do when the middle mouse button is released, and Loop should be closed.
     init(
-        openCallback: @escaping (WindowAction?) -> (),
+        openCallback: @escaping (WindowAction) -> (),
         closeCallback: @escaping (Bool) -> ()
     ) {
         // We will never start off with an action from this trigger, so pass in nil
@@ -76,11 +76,11 @@ final class MiddleClickTrigger {
             if event.type == .otherMouseDown,
                event.getIntegerValueField(.mouseEventButtonNumber) == 2 {
                 if doubleClickToTrigger {
-                    doubleClickTimer.handleTrigger(startingAction: nil)
+                    doubleClickTimer.handleTrigger(startingAction: .init(.noSelection))
                 } else if useTriggerDelay {
-                    triggerDelayTimer.handleTrigger(startingAction: nil)
+                    triggerDelayTimer.handleTrigger(startingAction: .init(.noSelection))
                 } else {
-                    openCallback(nil)
+                    openCallback(.init(.noSelection))
                 }
             } else {
                 triggerDelayTimer.cancel()
diff --git a/Loop/Core/Observers/MouseInteractionObserver.swift b/Loop/Core/Observers/MouseInteractionObserver.swift
index 6a47c037..d85b4077 100644
--- a/Loop/Core/Observers/MouseInteractionObserver.swift
+++ b/Loop/Core/Observers/MouseInteractionObserver.swift
@@ -23,10 +23,12 @@ final class MouseInteractionObserver {
     private var previousAngleToMouse: Angle = .zero
     private var previousDistanceToMouse: CGFloat = .zero
 
-    private var radialMenuActions: [RadialMenuWindowAction] {
-        Defaults[.radialMenuActions]
+    private var radialMenuActions: [RadialMenuAction] {
+        RadialMenuAction.userConfiguredActions
     }
 
+    private static let failedToResolveKeybindAction: WindowAction = .init(.noAction) // This helps to keep a stable ID
+
     init(
         windowActionCache: WindowActionCache,
         changeAction: @escaping (WindowAction) -> (),
@@ -86,7 +88,7 @@ final class MouseInteractionObserver {
         let initialMousePosition = getInitialMousePosition()
         let currentMousePosition = NSEvent.mouseLocation
 
-        let angleToMouse = Angle(radians: initialMousePosition.angle(to: currentMousePosition))
+        let angleToMouse = initialMousePosition.angle(to: currentMousePosition) + .radians(.pi / 2)
         let distanceToMouse = initialMousePosition.distance(to: currentMousePosition)
 
         // Return if the mouse didn't move
@@ -101,7 +103,7 @@ final class MouseInteractionObserver {
         previousAngleToMouse = angleToMouse
         previousDistanceToMouse = distanceToMouse
 
-        var newAction: RadialMenuWindowAction? = nil
+        var newAction: RadialMenuAction? = nil
 
         // If mouse over 50 points away, select half or quarter positions
         if distanceToMouse > 50 - Defaults[.radialMenuThickness] {
@@ -110,23 +112,27 @@ final class MouseInteractionObserver {
                 return
             }
 
-            let actions = Array(radialMenuActions[1...])
+            let actions = radialMenuActions.dropLast()
             let actionAngleSpan = 360.0 / CGFloat(actions.count)
             let halfAngleSpan = actionAngleSpan / 2.0
             let index = Int((angleToMouse.normalized().degrees + halfAngleSpan) / actionAngleSpan) % actions.count
             newAction = actions[index]
         } else if distanceToMouse > noActionDistance {
-            newAction = radialMenuActions.first
+            newAction = radialMenuActions.last
         }
 
         Task { @MainActor in
-            switch newAction {
+            switch newAction?.type {
             case let .custom(windowAction):
                 changeAction(windowAction)
             case let .keybindReference(id):
-                if let action = windowActionCache.actionsByIdentifier[id] { changeAction(action) }
+                if let action = windowActionCache.actionsByIdentifier[id] {
+                    changeAction(action)
+                } else {
+                    changeAction(Self.failedToResolveKeybindAction)
+                }
             case nil:
-                changeAction(.init(.noAction))
+                changeAction(.init(.noSelection))
             }
         }
     }
diff --git a/Loop/Extensions/CGGeometry+Extensions.swift b/Loop/Extensions/CGGeometry+Extensions.swift
index 39e382b7..7d70a346 100644
--- a/Loop/Extensions/CGGeometry+Extensions.swift
+++ b/Loop/Extensions/CGGeometry+Extensions.swift
@@ -14,12 +14,11 @@ extension CGFloat {
 }
 
 extension CGPoint {
-    func angle(to comparisonPoint: CGPoint) -> CGFloat {
+    func angle(to comparisonPoint: CGPoint) -> Angle {
         let originX = comparisonPoint.x - x
         let originY = comparisonPoint.y - y
         let bearingRadians = -atan2f(Float(originY), Float(originX))
-
-        return CGFloat(bearingRadians)
+        return .radians(Double(bearingRadians))
     }
 
     func distance(to comparisonPoint: CGPoint) -> CGFloat {
diff --git a/Loop/Extensions/Defaults+Extensions.swift b/Loop/Extensions/Defaults+Extensions.swift
index 5bff42a8..e9a48a9d 100644
--- a/Loop/Extensions/Defaults+Extensions.swift
+++ b/Loop/Extensions/Defaults+Extensions.swift
@@ -77,6 +77,7 @@ extension Defaults.Keys {
     static let ignoreFullscreen = Key<Bool>("ignoreFullscreen", default: false, iCloud: true)
     static let hideUntilDirectionIsChosen = Key<Bool>("hideUntilDirectionIsChosen", default: false, iCloud: true)
     static let hapticFeedback = Defaults.Key<Bool>("hapticFeedback", default: true, iCloud: true)
+    static let enableRadialMenuCustomization = Defaults.Key<Bool>("enableRadialMenuCustomization", default: true, iCloud: true)
 
     // About
     static let includeDevelopmentVersions = Key<Bool>("includeDevelopmentVersions", default: false, iCloud: true)
@@ -116,18 +117,17 @@ extension Defaults.Keys {
     static let previewStartingPosition = Key<PreviewStartingPosition>("previewStartingPosition", default: .screenCenter, iCloud: true)
 
     // Radial Menu
-    static let radialMenuActions = Key<[RadialMenuWindowAction]>(
-        "radialMenuActions",
-        default: RadialMenuWindowAction.defaultRadialMenuActions
-    )
+    static let radialMenuActions = Key<[RadialMenuAction]>("radialMenuActions", default: RadialMenuAction.defaultRadialMenuActions)
 
     // Migrator
     static let lastMigratorURL = Key<URL?>("lastMigratorURL", default: nil)
 
     // StashManager
-    static let stashManagerRevealedWindows = Key<Set<CGWindowID>>("stashManagerRevealed", default: Set<CGWindowID>())
     static let stashManagerStashedWindows = Key<[CGWindowID: WindowAction]>("stashManagerStashed", default: [:])
 
+    @available(*, deprecated, message: "Revealed stash windows are no longer tracked.")
+    static let stashManagerRevealedWindows = Key<Set<CGWindowID>>("stashManagerRevealed", default: Set<CGWindowID>())
+
     // AccentColorController
     static let lastUsedAccentColor1 = Key<Color>("lastUsedAccentColor1", default: .black)
     static let lastUsedAccentColor2 = Key<Color>("lastUsedAccentColor2", default: .black)
@@ -139,5 +139,5 @@ extension Defaults.Keys {
     static let processWallpaper = Key<Bool>("processWallpaper", default: false, iCloud: true)
 
     // DataPatcher
-    static let patchesApplied = Key<DataPatcher.Patch>("patchesApplied", default: [], iCloud: true)
+    static let patchesApplied = Key<DataPatcher.Patches>("patchesApplied", default: [], iCloud: true)
 }
diff --git a/Loop/Extensions/View+Extensions.swift b/Loop/Extensions/View+Extensions.swift
new file mode 100644
index 00000000..48a12a11
--- /dev/null
+++ b/Loop/Extensions/View+Extensions.swift
@@ -0,0 +1,52 @@
+//
+//  View+Extensions.swift
+//  Loop
+//
+//  Created by Kai Azim on 2023-06-14.
+//
+
+import SwiftUI
+
+extension View {
+    @inlinable
+    @ViewBuilder
+    func onChange(
+        of value: some Equatable,
+        initial: Bool,
+        action: @escaping () -> ()
+    ) -> some View {
+        if initial {
+            onChange(of: value) { _ in
+                action()
+            }
+            .onAppear {
+                action()
+            }
+        } else {
+            onChange(of: value) { _ in
+                action()
+            }
+        }
+    }
+
+    @inlinable
+    @ViewBuilder
+    func onChange<V>(
+        of value: V,
+        initial: Bool,
+        action: @escaping (V) -> ()
+    ) -> some View where V: Equatable {
+        if initial {
+            onChange(of: value) { newValue in
+                action(newValue)
+            }
+            .onAppear {
+                action(value)
+            }
+        } else {
+            onChange(of: value) { newValue in
+                action(newValue)
+            }
+        }
+    }
+}
diff --git a/Loop/Localizable.xcstrings b/Loop/Localizable.xcstrings
index c3bf6f55..09f13499 100644
--- a/Loop/Localizable.xcstrings
+++ b/Loop/Localizable.xcstrings
@@ -659,6 +659,9 @@
         }
       }
     },
+    "Actions" : {
+      "comment" : "Section header shown in settings"
+    },
     "Add" : {
       "comment" : "Used to add items to a list",
       "localizations" : {
@@ -742,6 +745,10 @@
         }
       }
     },
+    "Allow radial menu customization" : {
+      "comment" : "A toggle that allows users to enable or disable the ability to customize the actions available in the radial menu.",
+      "isCommentAutoGenerated" : true
+    },
     "Almost Maximize" : {
       "comment" : "Window action",
       "localizations" : {
@@ -2309,6 +2316,10 @@
         }
       }
     },
+    "Cancel" : {
+      "comment" : "The \"Cancel\" and \"Reset\" buttons in the reset radial menu actions alert.",
+      "isCommentAutoGenerated" : true
+    },
     "Center" : {
       "comment" : "Window action",
       "localizations" : {
@@ -2806,6 +2817,7 @@
       }
     },
     "Configure padding…" : {
+      "extractionState" : "stale",
       "localizations" : {
         "ar" : {
           "stringUnit" : {
@@ -3549,6 +3561,10 @@
         }
       }
     },
+    "Custom Action" : {
+      "comment" : "Label for the text field that allows the user to set a custom action name.",
+      "isCommentAutoGenerated" : true
+    },
     "Custom Cycle" : {
       "localizations" : {
         "ar" : {
@@ -3632,6 +3648,7 @@
       }
     },
     "Custom Keybind" : {
+      "extractionState" : "stale",
       "localizations" : {
         "ar" : {
           "stringUnit" : {
@@ -3713,6 +3730,10 @@
         }
       }
     },
+    "Customize this action's custom frame." : {
+      "comment" : "A help text describing the customization option for a custom-direction action.",
+      "isCommentAutoGenerated" : true
+    },
     "Customize this keybind's action." : {
       "localizations" : {
         "ar" : {
@@ -3796,6 +3817,7 @@
       }
     },
     "Customize this keybind's custom frame." : {
+      "extractionState" : "stale",
       "localizations" : {
         "ar" : {
           "stringUnit" : {
@@ -3877,7 +3899,12 @@
         }
       }
     },
+    "Customize what this action cycles through." : {
+      "comment" : "A description for a button that appears when configuring a cycling window action.",
+      "isCommentAutoGenerated" : true
+    },
     "Customize what this keybind cycles through." : {
+      "extractionState" : "stale",
       "localizations" : {
         "ar" : {
           "stringUnit" : {
@@ -5360,6 +5387,10 @@
         }
       }
     },
+    "Failed to resolve linked keybind" : {
+      "comment" : "An error message displayed when a linked keybind cannot be resolved.",
+      "isCommentAutoGenerated" : true
+    },
     "First Fourth" : {
       "comment" : "Window action",
       "localizations" : {
@@ -11220,6 +11251,9 @@
         }
       }
     },
+    "Left-click to step through cycle actions." : {
+      "comment" : "Section footer shown in settings"
+    },
     "Locked icon alert title" : {
       "localizations" : {
         "ar" : {
@@ -15585,6 +15619,10 @@
         }
       }
     },
+    "No radial menu actions" : {
+      "comment" : "A message shown when there are no actions configured for the radial menu.",
+      "isCommentAutoGenerated" : true
+    },
     "No updates available message 01" : {
       "localizations" : {
         "ar" : {
@@ -20426,6 +20464,10 @@
         }
       }
     },
+    "Press \"Add\" to add an action" : {
+      "comment" : "A description displayed below the list of radial menu actions, encouraging the user to add more.",
+      "isCommentAutoGenerated" : true
+    },
     "Press \"Add\" to add an application" : {
       "localizations" : {
         "ar" : {
@@ -20923,6 +20965,7 @@
       }
     },
     "Quit" : {
+      "extractionState" : "stale",
       "localizations" : {
         "ar" : {
           "stringUnit" : {
@@ -21169,6 +21212,9 @@
         }
       }
     },
+    "Radial Menu" : {
+      "comment" : "Section header shown in settings"
+    },
     "Relaxed" : {
       "comment" : "Animation speed setting",
       "localizations" : {
@@ -21581,6 +21627,17 @@
           }
         }
       }
+    },
+    "Reset keybinds?" : {
+      "comment" : "An alert title that asks the user if they want to reset all keybinds.",
+      "isCommentAutoGenerated" : true
+    },
+    "Reset radial menu actions" : {
+      "comment" : "A button label that resets the radial menu actions to their default configuration.",
+      "isCommentAutoGenerated" : true
+    },
+    "Reset radial menu actions?" : {
+
     },
     "Resize window under cursor" : {
       "localizations" : {
@@ -26694,6 +26751,18 @@
         }
       }
     },
+    "This action is linked to a keybind. Changes made to this action will affect both." : {
+      "comment" : "A tooltip explaining that changes to a radial menu action will also affect the corresponding keybind.",
+      "isCommentAutoGenerated" : true
+    },
+    "This will reset all keybinds to their original defaults." : {
+      "comment" : "A message displayed in an alert when the user confirms resetting all keybinds.",
+      "isCommentAutoGenerated" : true
+    },
+    "This will reset all radial menu actions to their default configuration." : {
+      "comment" : "An alert message explaining that resetting the radial menu actions will reset them to their default configuration.",
+      "isCommentAutoGenerated" : true
+    },
     "To save power, window animations are\nunavailable in Low Power Mode." : {
       "localizations" : {
         "ar" : {
@@ -30000,5 +30069,5 @@
       }
     }
   },
-  "version" : "1.0"
+  "version" : "1.1"
 }
\ No newline at end of file
diff --git a/Loop/Settings Window/Loop/AdvancedConfiguration.swift b/Loop/Settings Window/Loop/AdvancedConfiguration.swift
index f7ad1f30..f4cf90ab 100644
--- a/Loop/Settings Window/Loop/AdvancedConfiguration.swift	
+++ b/Loop/Settings Window/Loop/AdvancedConfiguration.swift	
@@ -11,10 +11,12 @@ import Luminare
 import Scribe
 import SwiftUI
 
+@MainActor
 final class AdvancedConfigurationModel: ObservableObject {
-    @Published private(set) var didImportSuccessfullyAlert = false
-    @Published private(set) var didExportSuccessfullyAlert = false
-    @Published private(set) var didResetSuccessfullyAlert = false
+    @Published private(set) var showResetRadialMenuActionsSuccessIndicator = false
+    @Published private(set) var showImportKeybindsSuccessIndicator = false
+    @Published private(set) var showExportKeybindsSuccessIndicator = false
+    @Published private(set) var showResetKeybindsSuccessIndicator = false
 
     @Published private(set) var isLowPowerModeEnabled: Bool = ProcessInfo.processInfo.isLowPowerModeEnabled
     @Published private(set) var isAccessibilityAccessGranted = AccessibilityManager.shared.isGranted
@@ -66,7 +68,9 @@ final class AdvancedConfigurationModel: ObservableObject {
     func importPrompt() {
         Task {
             do {
-                try await Migrator.importPrompt(onSuccess: importedSuccessfully)
+                try await Migrator.importPrompt {
+                    showSuccessIndicator(\.showImportKeybindsSuccessIndicator)
+                }
             } catch {
                 Log.error("Error importing keybinds: \(error)", category: .advancedConfigurationModel)
             }
@@ -77,7 +81,9 @@ final class AdvancedConfigurationModel: ObservableObject {
     func exportPrompt() {
         Task {
             do {
-                try await Migrator.exportPrompt(onSuccess: exportedSuccessfully)
+                try await Migrator.exportPrompt {
+                    showSuccessIndicator(\.showExportKeybindsSuccessIndicator)
+                }
             } catch {
                 Log.error("Error exporting keybinds: \(error)", category: .advancedConfigurationModel)
             }
@@ -85,56 +91,33 @@ final class AdvancedConfigurationModel: ObservableObject {
     }
 
     /// Resets keybinds to default values.
-    func reset() {
+    func resetKeybinds() {
         Defaults.reset(.keybinds)
-        resetSuccessfully()
+        showSuccessIndicator(\.showResetKeybindsSuccessIndicator)
     }
 
-    private func importedSuccessfully() {
-        DispatchQueue.main.async { [weak self] in
-            withAnimation(.smooth(duration: 0.5)) {
-                self?.didImportSuccessfullyAlert = true
-            }
-        }
-
-        DispatchQueue.main.asyncAfter(deadline: .now() + 2) { [weak self] in
-            withAnimation(.smooth(duration: 0.5)) {
-                self?.didImportSuccessfullyAlert = false
-            }
-        }
+    func resetRadialMenuActions() {
+        Defaults.reset(.radialMenuActions)
+        showSuccessIndicator(\.showResetRadialMenuActionsSuccessIndicator)
     }
 
-    private func exportedSuccessfully() {
-        DispatchQueue.main.async { [weak self] in
-            withAnimation(.smooth(duration: 0.5)) {
-                self?.didExportSuccessfullyAlert = true
-            }
-        }
-
-        DispatchQueue.main.asyncAfter(deadline: .now() + 2) { [weak self] in
+    private func showSuccessIndicator(_ keyPath: ReferenceWritableKeyPath<AdvancedConfigurationModel, Bool>) {
+        Task {
             withAnimation(.smooth(duration: 0.5)) {
-                self?.didExportSuccessfullyAlert = false
+                self[keyPath: keyPath] = true
             }
-        }
-    }
 
-    private func resetSuccessfully() {
-        DispatchQueue.main.async { [weak self] in
-            withAnimation(.smooth(duration: 0.5)) {
-                self?.didResetSuccessfullyAlert = true
-            }
-        }
+            try? await Task.sleep(for: .seconds(2))
 
-        DispatchQueue.main.asyncAfter(deadline: .now() + 2) { [weak self] in
             withAnimation(.smooth(duration: 0.5)) {
-                self?.didResetSuccessfullyAlert = false
+                self[keyPath: keyPath] = false
             }
         }
     }
 }
 
 struct AdvancedConfigurationView: View {
-    @Environment(\.luminareTintColor) var tint
+    @EnvironmentObject private var windowModel: SettingsWindowManager
     @Environment(\.luminareAnimation) var luminareAnimation
     @Environment(\.openURL) private var openURL
 
@@ -148,21 +131,29 @@ struct AdvancedConfigurationView: View {
     @Default(.ignoreFullscreen) var ignoreFullscreen
     @Default(.hapticFeedback) var hapticFeedback
     @Default(.sizeIncrement) var sizeIncrement
+    @Default(.enableRadialMenuCustomization) var enableRadialMenuCustomization
+
+    @State private var isConfirmingResetKeybinds: Bool = false
+    @State private var isConfirmingResetRadialMenuActions: Bool = false
 
     private var showLowPowerModeWarning: Bool {
         animateWindowResizes && !ignoreLowPowerMode && model.isLowPowerModeEnabled
     }
 
     var body: some View {
-        generalSection
-        keybindsSection
-        permissionsSection
-            .onAppear(perform: model.startTracking)
-            .onDisappear(perform: model.stopTracking)
+        Group {
+            generalSection
+            radialMenuSection
+            keybindsSection
+            permissionsSection
+                .onAppear(perform: model.startTracking)
+                .onDisappear(perform: model.stopTracking)
+        }
+        .animation(luminareAnimation, value: enableRadialMenuCustomization)
     }
 
     private var generalSection: some View {
-        LuminareSection(String(localized: "General", comment: "Section header shown in settings")) {
+        LuminareSection {
             if #available(macOS 15.0, *) {
                 LuminareToggle("Use macOS window manager when available", isOn: $useSystemWindowManagerWhenAvailable)
             }
@@ -194,7 +185,6 @@ struct AdvancedConfigurationView: View {
 
             LuminareToggle("Disable cursor interaction", isOn: $disableCursorInteraction)
             LuminareToggle("Ignore fullscreen windows", isOn: $ignoreFullscreen)
-            LuminareToggle("Hide until direction is chosen", isOn: $hideUntilDirectionIsChosen)
             LuminareToggle("Haptic feedback", isOn: $hapticFeedback)
 
             LuminareSlider(
@@ -209,6 +199,51 @@ struct AdvancedConfigurationView: View {
         }
     }
 
+    private var radialMenuSection: some View {
+        LuminareSection(String(localized: "Radial Menu", comment: "Section header shown in settings")) {
+            LuminareToggle("Hide until direction is chosen", isOn: $hideUntilDirectionIsChosen)
+
+            LuminareToggle(isOn: $enableRadialMenuCustomization) {
+                HStack {
+                    Text("Allow radial menu customization")
+
+                    if enableRadialMenuCustomization {
+                        Button {
+                            windowModel.currentTab = .radialMenu
+                        } label: {
+                            Image(systemName: "arrow.up.right.square.fill")
+                                .foregroundStyle(.secondary)
+                        }
+                        .buttonStyle(.plain)
+                    }
+                }
+            }
+
+            if enableRadialMenuCustomization {
+                Button(role: .destructive) {
+                    isConfirmingResetRadialMenuActions = true
+                } label: {
+                    HStack {
+                        Text("Reset radial menu actions")
+
+                        if model.showResetRadialMenuActionsSuccessIndicator {
+                            Image(systemName: "checkmark")
+                                .foregroundStyle(.green)
+                                .bold()
+                        }
+                    }
+                }
+                .luminareRoundingBehavior(bottom: true)
+                .alert("Reset radial menu actions?", isPresented: $isConfirmingResetRadialMenuActions) {
+                    Button("Cancel", role: .cancel) {}
+                    Button("Reset", role: .destructive, action: model.resetRadialMenuActions)
+                } message: {
+                    Text("This will reset all radial menu actions to their default configuration.")
+                }
+            }
+        }
+    }
+
     private var keybindsSection: some View {
         LuminareSection(String(localized: "Keybinds", comment: "Section header shown in settings")) {
             HStack(spacing: 4) {
@@ -216,9 +251,9 @@ struct AdvancedConfigurationView: View {
                     HStack {
                         Text("Import")
 
-                        if model.didImportSuccessfullyAlert {
+                        if model.showImportKeybindsSuccessIndicator {
                             Image(systemName: "checkmark")
-                                .foregroundStyle(tint)
+                                .foregroundStyle(.green)
                                 .bold()
                         }
                     }
@@ -229,26 +264,34 @@ struct AdvancedConfigurationView: View {
                     HStack {
                         Text("Export")
 
-                        if model.didExportSuccessfullyAlert {
+                        if model.showExportKeybindsSuccessIndicator {
                             Image(systemName: "checkmark")
-                                .foregroundStyle(tint)
+                                .foregroundStyle(.green)
                                 .bold()
                         }
                     }
                 }
 
-                Button(role: .destructive, action: model.reset) {
+                Button(role: .destructive) {
+                    isConfirmingResetKeybinds = true
+                } label: {
                     HStack {
                         Text("Reset")
 
-                        if model.didResetSuccessfullyAlert {
+                        if model.showResetKeybindsSuccessIndicator {
                             Image(systemName: "checkmark")
-                                .foregroundStyle(tint)
+                                .foregroundStyle(.green)
                                 .bold()
                         }
                     }
                 }
                 .luminareRoundingBehavior(trailing: true)
+                .alert("Reset keybinds?", isPresented: $isConfirmingResetKeybinds) {
+                    Button("Cancel", role: .cancel) {}
+                    Button("Reset", role: .destructive, action: model.resetKeybinds)
+                } message: {
+                    Text("This will reset all keybinds to their original defaults.")
+                }
             }
         }
     }
@@ -265,7 +308,7 @@ struct AdvancedConfigurationView: View {
             HStack {
                 if model.isAccessibilityAccessGranted {
                     Image(systemName: "checkmark.seal.fill")
-                        .foregroundStyle(tint)
+                        .foregroundStyle(.green)
                 }
 
                 Text("Accessibility access")
diff --git a/Loop/Settings Window/Settings/Keybinds/Item View/DirectionPickerView.swift b/Loop/Settings Window/Settings/Keybinds/DirectionPickerView.swift
similarity index 54%
rename from Loop/Settings Window/Settings/Keybinds/Item View/DirectionPickerView.swift
rename to Loop/Settings Window/Settings/Keybinds/DirectionPickerView.swift
index a55b4d11..d2c65d37 100644
--- a/Loop/Settings Window/Settings/Keybinds/Item View/DirectionPickerView.swift	
+++ b/Loop/Settings Window/Settings/Keybinds/DirectionPickerView.swift	
@@ -16,22 +16,9 @@ struct DirectionPickerView: View {
     @Binding private var direction: WindowDirection
     private let isInCycle: Bool
 
-    private static let sections: [PickerSection] = [
-        .init(String(localized: "General", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.general),
-        .init(String(localized: "Halves", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.halves),
-        .init(String(localized: "Quarters", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.quarters),
-        .init(String(localized: "Horizontal Thirds", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.horizontalThirds),
-        .init(String(localized: "Vertical Thirds", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.verticalThirds),
-        .init(String(localized: "Horizontal Fourths", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.horizontalFourths),
-        .init(String(localized: "Screen Switching", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.screenSwitching),
-        .init(String(localized: "Size Adjustment", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.sizeAdjustment),
-        .init(String(localized: "Shrink", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.shrink),
-        .init(String(localized: "Grow", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.grow),
-        .init(String(localized: "Move", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.move),
-        .init(String(localized: "Focus", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.focus),
-        .init(String(localized: "Stash", comment: "Section header in the action picker of the Keybinds tab"), [WindowDirection.stash, WindowDirection.unstash]),
-        .init(String(localized: "Go Back", comment: "Section header in the action picker of the Keybinds tab"), [WindowDirection.initialFrame, WindowDirection.undo])
-    ]
+    private var sections: [PickerSection<WindowDirection>] {
+        PickerSection.windowDirections
+    }
 
     private var moreSection: PickerSection<WindowDirection> {
         let title = String(localized: "More", comment: "Section header in the action picker of the Keybinds tab")
@@ -43,13 +30,9 @@ struct DirectionPickerView: View {
     }
 
     private var sectionItems: [WindowDirection] {
-        var result: [WindowDirection] = []
-
-        for sectionItems in Self.sections.map(\.items) {
-            result.append(contentsOf: sectionItems)
-        }
-
-        return result
+        sections
+            .map(\.items)
+            .flatMap(\.self)
     }
 
     init(direction: Binding<WindowDirection>, isInCycle: Bool) {
@@ -59,8 +42,11 @@ struct DirectionPickerView: View {
 
     var body: some View {
         VStack(spacing: 0) {
-            CustomTextField($searchText)
-                .padding(padding)
+            CustomTextField(
+                $searchText,
+                placeholder: .init(localized: "Search for a window action", defaultValue: "Search…")
+            )
+            .padding(padding)
 
             Divider()
 
@@ -68,7 +54,7 @@ struct DirectionPickerView: View {
                 $direction,
                 $searchResults,
                 padding,
-                Self.sections + [moreSection]
+                sections + [moreSection]
             ) { item in
                 HStack(spacing: 8) {
                     IconView(action: .init(item))
diff --git a/Loop/Settings Window/Settings/Keybinds/Item View/KeybindItemView.swift b/Loop/Settings Window/Settings/Keybinds/KeybindItemView.swift
similarity index 93%
rename from Loop/Settings Window/Settings/Keybinds/Item View/KeybindItemView.swift
rename to Loop/Settings Window/Settings/Keybinds/KeybindItemView.swift
index 17ceab3a..27b3bf53 100644
--- a/Loop/Settings Window/Settings/Keybinds/Item View/KeybindItemView.swift	
+++ b/Loop/Settings Window/Settings/Keybinds/KeybindItemView.swift	
@@ -64,11 +64,11 @@ struct KeybindItemView: View {
 
             Group {
                 if action.direction.isCustomizable {
-                    Button(action: {
+                    Button {
                         isConfiguringCustom = true
-                    }, label: {
+                    } label: {
                         Image(systemName: "slider.horizontal.3")
-                    })
+                    }
                     .buttonStyle(.plain)
                     .luminareModalWithPredefinedSheetStyle(isPresented: $isConfiguringCustom, isCompact: false) {
                         if action.direction == .custom {
@@ -79,21 +79,21 @@ struct KeybindItemView: View {
                                 .frame(width: 400)
                         }
                     }
-                    .help("Customize this keybind's custom frame.")
+                    .help("Customize this action's custom frame.")
                 }
 
                 if action.direction == .cycle {
-                    Button(action: {
+                    Button {
                         isConfiguringCycle = true
-                    }, label: {
+                    } label: {
                         Image(systemName: "repeat")
-                    })
+                    }
                     .buttonStyle(.plain)
                     .luminareModalWithPredefinedSheetStyle(isPresented: $isConfiguringCycle, isCompact: false) {
                         CycleActionConfigurationView(action: $action, isPresented: $isConfiguringCycle)
                             .frame(width: 400)
                     }
-                    .help("Customize what this keybind cycles through.")
+                    .help("Customize what this action cycles through.")
                 }
             }
             .font(.title3)
@@ -164,10 +164,7 @@ struct KeybindItemView: View {
             }
             .padding(.horizontal, 4)
         }
-        .luminareContentSize(
-            contentMode: .fit,
-            hasFixedHeight: true
-        )
+        .luminareContentSize(contentMode: .fit, hasFixedHeight: true)
         .luminareRoundingBehavior(top: true, bottom: true)
         .luminareFilledStates([.hovering, .pressed])
         .luminareBorderedStates(.hovering)
diff --git a/Loop/Settings Window/Settings/Keybinds/KeybindsConfigurationView.swift b/Loop/Settings Window/Settings/Keybinds/KeybindsConfigurationView.swift
index c454693c..f4fa7096 100644
--- a/Loop/Settings Window/Settings/Keybinds/KeybindsConfigurationView.swift	
+++ b/Loop/Settings Window/Settings/Keybinds/KeybindsConfigurationView.swift	
@@ -16,7 +16,7 @@ final class KeybindsConfigurationModel: ObservableObject {
 
 struct KeybindsConfigurationView: View {
     @Environment(\.luminareAnimation) private var luminareAnimation
-
+    @EnvironmentObject private var windowModel: SettingsWindowManager
     @StateObject private var model = KeybindsConfigurationModel()
 
     @Default(.triggerKey) private var triggerKey
@@ -163,6 +163,17 @@ struct KeybindsConfigurationView: View {
                 .padding()
             }
             .luminareRoundingBehavior(bottom: true)
+            .onChange(of: model.selectedKeybinds, initial: true) {
+                if model.selectedKeybinds.count == 1, let action = model.selectedKeybinds.first {
+                    windowModel.isPreviewingUserSelection = true
+                    windowModel.setPreviewedAction(to: action)
+                } else {
+                    windowModel.isPreviewingUserSelection = false
+                }
+            }
+            .onDisappear {
+                windowModel.isPreviewingUserSelection = false
+            }
         }
     }
 }
diff --git a/Loop/Settings Window/Settings/Keybinds/Modal Views/CustomActionConfigurationView.swift b/Loop/Settings Window/Settings/Keybinds/Modal Views/CustomActionConfigurationView.swift
index 686d4dca..0cbe2e9d 100644
--- a/Loop/Settings Window/Settings/Keybinds/Modal Views/CustomActionConfigurationView.swift	
+++ b/Loop/Settings Window/Settings/Keybinds/Modal Views/CustomActionConfigurationView.swift	
@@ -39,6 +39,10 @@ struct CustomActionConfigurationView: View {
     private let previewController = PreviewController()
     private let screenSize: CGSize = NSScreen.main?.frame.size ?? NSScreen.screens[0].frame.size
 
+    private var showMacOSCenterToggle: Bool {
+        action.anchor ?? .center == .center || action.anchor == .macOSCenter
+    }
+
     init(action: Binding<WindowAction>, isPresented: Binding<Bool>) {
         _windowAction = action
         _isPresented = isPresented
@@ -77,7 +81,7 @@ struct CustomActionConfigurationView: View {
     private func configurationSections() -> some View {
         LuminareSection(outerPadding: 0) {
             LuminareTextField(
-                "Custom Keybind",
+                "Custom Action",
                 text: Binding(
                     get: { action.name ?? "" },
                     set: { action.name = $0 }
@@ -221,9 +225,9 @@ struct CustomActionConfigurationView: View {
                 ) { anchor in
                     IconView(action: anchor.iconAction)
                 }
-                .luminareRoundingBehavior(bottom: true)
+                .luminareRoundingBehavior(bottom: !showMacOSCenterToggle)
 
-                if action.anchor ?? .center == .center || action.anchor == .macOSCenter {
+                if showMacOSCenterToggle {
                     LuminareToggle(
                         isOn: Binding(
                             get: {
diff --git a/Loop/Settings Window/Settings/Keybinds/Modal Views/CycleActionConfigurationView.swift b/Loop/Settings Window/Settings/Keybinds/Modal Views/CycleActionConfigurationView.swift
index 100a3fc1..1077698c 100644
--- a/Loop/Settings Window/Settings/Keybinds/Modal Views/CycleActionConfigurationView.swift	
+++ b/Loop/Settings Window/Settings/Keybinds/Modal Views/CycleActionConfigurationView.swift	
@@ -52,11 +52,7 @@ struct CycleActionConfigurationView: View {
                 LuminareList(
                     items: Binding(
                         get: {
-                            if action.cycle == nil {
-                                action.cycle = []
-                            }
-
-                            return action.cycle ?? []
+                            action.cycle ?? []
                         }, set: { newValue in
                             action.cycle = newValue
                         }
@@ -95,5 +91,10 @@ struct CycleActionConfigurationView: View {
             }
             .luminareCornerRadius(8)
         }
+        .onAppear {
+            if action.cycle == nil {
+                action.cycle = []
+            }
+        }
     }
 }
diff --git a/Loop/Settings Window/SettingsContentView.swift b/Loop/Settings Window/SettingsContentView.swift
index 4917569c..972119bf 100644
--- a/Loop/Settings Window/SettingsContentView.swift	
+++ b/Loop/Settings Window/SettingsContentView.swift	
@@ -5,6 +5,7 @@
 //  Created by Kai Azim on 2025-10-18.
 //
 
+import Defaults
 import Luminare
 import SwiftUI
 
@@ -14,6 +15,7 @@ struct SettingsContentView: View {
 
     @Environment(\.luminareAnimation) private var animation
     @Environment(\.luminareTitleBarHeight) private var titleBarHeight
+    @Default(.enableRadialMenuCustomization) var enableRadialMenuCustomization
 
     var body: some View {
         LuminareDividedStack {
@@ -51,18 +53,21 @@ struct SettingsContentView: View {
 
             if model.showInspector {
                 ZStack {
-                    if model.showPreview {
-                        LuminarePreviewView()
-                    }
+                    LuminarePreviewView()
+                        .allowsHitTesting(false)
 
                     if model.showRadialMenu {
-                        VStack {
-                            RadialMenuView(viewModel: model.radialMenuViewModel)
+                        RadialMenuView(viewModel: model.radialMenuViewModel)
+                            .allowsHitTesting(false)
+
+                        if enableRadialMenuCustomization, model.currentTab == .radialMenu {
+                            RadialMenuActionsGuide()
                         }
-                        .frame(maxHeight: .infinity, alignment: .center)
                     }
                 }
+                .compositingGroup()
                 .animation(animation, value: [model.showRadialMenu, model.showPreview])
+                .padding(12)
                 .frame(width: 520)
             }
         }
@@ -74,5 +79,6 @@ struct SettingsContentView: View {
         }
         .luminareTint(overridingWith: accentColorController.color1)
         .ignoresSafeArea()
+        .environmentObject(model)
     }
 }
diff --git a/Loop/Settings Window/SettingsWindowManager.swift b/Loop/Settings Window/SettingsWindowManager.swift
index c8fa2484..8e7ffa23 100644
--- a/Loop/Settings Window/SettingsWindowManager.swift	
+++ b/Loop/Settings Window/SettingsWindowManager.swift	
@@ -17,7 +17,14 @@ final class SettingsWindowManager: ObservableObject {
     private var controller: NSWindowController?
     private var previewActionTimerTask: Task<(), Error>?
 
-    @Published private(set) var previewedAction: WindowAction
+    @Published var isPreviewingUserSelection: Bool = false {
+        didSet { restartTimer() }
+    }
+
+    @Published private(set) var previewedParentAction: WindowAction? = nil
+    @Published private(set) var previewedAction: WindowAction = .init(.noSelection) {
+        didSet { radialMenuViewModel.setAction(to: previewedAction, parent: previewedParentAction) }
+    }
 
     @Published var showRadialMenu: Bool = false
     @Published var showPreview: Bool = false
@@ -54,10 +61,13 @@ final class SettingsWindowManager: ObservableObject {
     }
 
     private init() {
-        let startingAction: WindowAction = .init(.topHalf)
+        let startingAction: WindowAction = .init(.noAction)
 
-        self.previewedAction = startingAction
         self.radialMenuViewModel = .init(startingAction: startingAction, window: nil, previewMode: true)
+
+        if let firstAction = RadialMenuAction.userConfiguredActions.first?.resolved {
+            setPreviewedAction(to: firstAction)
+        }
     }
 
     func show() {
@@ -108,18 +118,22 @@ final class SettingsWindowManager: ObservableObject {
         Log.success("Settings window closed", category: .settingsWindowManager)
     }
 
+    private func restartTimer() {
+        stopTimer()
+        startTimer()
+    }
+
     private func startTimer() {
         previewActionTimerTask?.cancel()
         previewActionTimerTask = Task(priority: .utility) {
-            while true {
-                try await Task.sleep(for: .seconds(1))
+            try await Task.sleep(for: .seconds(1))
 
-                if controller?.window?.isKeyWindow == true, !Task.isCancelled {
-                    await MainActor.run {
-                        previewedAction.direction = previewedAction.direction.nextPreviewDirection
-                        radialMenuViewModel.setAction(to: previewedAction)
-                    }
+            while !Task.isCancelled {
+                if controller?.window?.isKeyWindow == true {
+                    setNextPreviewedAction()
                 }
+
+                try await Task.sleep(for: .seconds(1))
             }
         }
     }
@@ -128,4 +142,40 @@ final class SettingsWindowManager: ObservableObject {
         previewActionTimerTask?.cancel()
         previewActionTimerTask = nil
     }
+
+    private func setNextPreviewedAction() {
+        if isPreviewingUserSelection {
+            guard let parent = previewedParentAction,
+                  parent.direction == .cycle,
+                  let cycle = parent.cycle,
+                  let index = cycle.firstIndex(of: previewedAction)
+            else {
+                return
+            }
+
+            let nextIndex = (index + 1) % cycle.count
+            setPreviewedAction(to: parent, cycleAction: cycle[nextIndex])
+        } else {
+            let radialMenuActions: [WindowAction] = RadialMenuAction.userConfiguredActions
+                .compactMap(\.resolved)
+
+            let nextAction = if let index = radialMenuActions.firstIndex(of: previewedParentAction ?? previewedAction) {
+                radialMenuActions[(index + 1) % radialMenuActions.count]
+            } else {
+                radialMenuActions.first ?? .init(.noAction)
+            }
+
+            setPreviewedAction(to: nextAction)
+        }
+    }
+
+    func setPreviewedAction(to newAction: WindowAction, cycleAction: WindowAction? = nil) {
+        if newAction.direction == .cycle {
+            previewedParentAction = newAction
+            previewedAction = cycleAction ?? newAction.cycle?.first ?? .init(.noAction)
+        } else {
+            previewedParentAction = nil
+            previewedAction = newAction
+        }
+    }
 }
diff --git a/Loop/Settings Window/Theming/AccentColorConfiguration.swift b/Loop/Settings Window/Theming/AccentColorConfiguration.swift
index fc485efc..5fef1654 100644
--- a/Loop/Settings Window/Theming/AccentColorConfiguration.swift	
+++ b/Loop/Settings Window/Theming/AccentColorConfiguration.swift	
@@ -12,7 +12,6 @@ import SwiftUI
 // MARK: - View
 
 struct AccentColorConfigurationView: View {
-    @Environment(\.luminareTintColor) var tint
     @Environment(\.luminareAnimation) private var luminareAnimation
     @ObservedObject private var accentColorController: AccentColorController = .shared
 
@@ -53,7 +52,7 @@ struct AccentColorConfigurationView: View {
 
                         if didSyncWallpaper {
                             Image(systemName: "checkmark")
-                                .foregroundStyle(tint)
+                                .foregroundStyle(.green)
                                 .bold()
                         }
                     }
diff --git a/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionItemView.swift b/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionItemView.swift
new file mode 100644
index 00000000..7a416e3c
--- /dev/null
+++ b/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionItemView.swift	
@@ -0,0 +1,228 @@
+//
+//  RadialMenuActionItemView.swift
+//  Loop
+//
+//  Created by Kai Azim on 2025-12-08.
+//
+
+import Defaults
+import Luminare
+import SwiftUI
+
+@MainActor
+final class RadialMenuWindowActionWrapper: ObservableObject {
+    @Published var isConfiguringCustom: Bool = false
+    @Published var isConfiguringCycle: Bool = false
+    @Published var action: RadialMenuAction {
+        didSet { updateBindingAction() }
+    }
+
+    private let bindingAction: Binding<RadialMenuAction>
+
+    init(binding action: Binding<RadialMenuAction>) {
+        self.action = action.wrappedValue
+        self.bindingAction = action
+    }
+
+    private func updateBindingAction() {
+        guard bindingAction.wrappedValue != action else { return }
+        bindingAction.wrappedValue = action
+
+        guard let resolvedAction = action.resolved else {
+            isConfiguringCustom = false
+            isConfiguringCycle = false
+            return
+        }
+
+        Task {
+            isConfiguringCustom = resolvedAction.direction.isCustomizable
+            isConfiguringCycle = resolvedAction.direction == .cycle
+        }
+    }
+}
+
+struct RadialMenuActionItemView: View {
+    @EnvironmentObject private var windowModel: SettingsWindowManager
+    @Environment(\.luminareItemBeingHovered) private var isHovering
+    @Environment(\.luminareAnimation) var luminareAnimation
+    @StateObject private var wrapper: RadialMenuWindowActionWrapper
+
+    @Default(.radialMenuActions) private var radialMenuActions
+    @Default(.keybinds) private var keybinds
+
+    private let moveUp: () -> ()
+    private let moveDown: () -> ()
+
+    @State private var isPickerPresented = false
+
+    init(
+        _ action: Binding<RadialMenuAction>,
+        moveUp: @escaping () -> (),
+        moveDown: @escaping () -> ()
+    ) {
+        self._wrapper = StateObject(wrappedValue: RadialMenuWindowActionWrapper(binding: action))
+        self.moveUp = moveUp
+        self.moveDown = moveDown
+    }
+
+    var body: some View {
+        HStack(spacing: 12) {
+            label
+
+            Spacer()
+
+            if wrapper.action.type.isKeybindReference {
+                Image(systemName: "keyboard")
+                    .foregroundStyle(.secondary)
+                    .help("This action is linked to a keybind. Changes made to this action will affect both.")
+            }
+
+            HStack(spacing: 8) {
+                Button(action: moveUp) {
+                    Image(systemName: "arrow.up")
+                        .frame(width: 27, height: 27)
+                        .font(.callout)
+                        .contentShape(.rect)
+                }
+                .luminareContentSize(aspectRatio: 1.0, contentMode: .fit, hasFixedHeight: true)
+                .luminareRoundingBehavior(top: true, bottom: true)
+
+                Button(action: moveDown) {
+                    Image(systemName: "arrow.down")
+                        .frame(width: 27, height: 27)
+                        .font(.callout)
+                        .contentShape(.rect)
+                }
+                .luminareContentSize(aspectRatio: 1.0, contentMode: .fit, hasFixedHeight: true)
+                .luminareRoundingBehavior(top: true, bottom: true)
+            }
+        }
+        .padding(.horizontal, 12)
+        .onChange(of: isHovering) { _ in
+            if !isHovering {
+                isPickerPresented = false
+            }
+        }
+    }
+
+    @ViewBuilder
+    private var label: some View {
+        actionIndicator
+            .background {
+                if isHovering {
+                    Color.clear
+                        .luminarePopup(
+                            isPresented: $isPickerPresented,
+                            alignment: .leadingLastTextBaseline
+                        ) {
+                            RadialMenuActionPickerView(selection: $wrapper.action.type)
+                        }
+                        .luminareSheetClosesOnDefocus(true)
+                }
+            }
+    }
+
+    @ViewBuilder
+    var actionIndicator: some View {
+        HStack(spacing: 2) {
+            Button {
+                isPickerPresented = true
+            } label: {
+                HStack(spacing: 8) {
+                    if let action = wrapper.action.resolved {
+                        IconView(action: action)
+
+                        Text(action.getName())
+                            .fontWeight(.regular)
+                            .lineLimit(1)
+                    } else {
+                        Image(systemName: "bolt.horizontal.fill")
+                            .foregroundStyle(.secondary)
+
+                        Text("Failed to resolve linked keybind")
+                            .foregroundStyle(.secondary)
+                    }
+                }
+                .padding(.horizontal, 4)
+            }
+            .luminareContentSize(contentMode: .fit, hasFixedHeight: true)
+            .luminareRoundingBehavior(top: true, bottom: true)
+            .luminareFilledStates([.hovering, .pressed])
+            .luminareBorderedStates(.hovering)
+            .luminareMinHeight(24)
+            .padding(.leading, -4)
+
+            Group {
+                if let resolvedAction = wrapper.action.resolved {
+                    let actionBinding = Binding<WindowAction>(
+                        get: {
+                            resolvedAction
+                        },
+                        set: { newAction in
+                            switch wrapper.action.type {
+                            case .custom:
+                                wrapper.action.type = .custom(newAction)
+                            case .keybindReference:
+                                guard let index = Defaults[.keybinds].firstIndex(where: { $0.id == wrapper.action.associatedActionId }) else {
+                                    return
+                                }
+
+                                keybinds[index] = newAction
+                            }
+                        }
+                    )
+
+                    if resolvedAction.direction.isCustomizable {
+                        Button {
+                            wrapper.isConfiguringCustom = true
+                        } label: {
+                            Image(systemName: "slider.horizontal.3")
+                        }
+                        .buttonStyle(.plain)
+                        .luminareModalWithPredefinedSheetStyle(
+                            isPresented: $wrapper.isConfiguringCustom,
+                            isCompact: false
+                        ) {
+                            if resolvedAction.direction == .custom {
+                                CustomActionConfigurationView(
+                                    action: actionBinding,
+                                    isPresented: $wrapper.isConfiguringCustom
+                                )
+                                .frame(width: 400)
+                            } else {
+                                StashActionConfigurationView(
+                                    action: actionBinding,
+                                    isPresented: $wrapper.isConfiguringCustom
+                                )
+                                .frame(width: 400)
+                            }
+                        }
+                        .help("Customize this action's custom frame.")
+                    }
+
+                    if resolvedAction.direction == .cycle {
+                        Button {
+                            wrapper.isConfiguringCycle = true
+                        } label: {
+                            Image(systemName: "repeat")
+                        }
+                        .buttonStyle(.plain)
+                        .luminareModalWithPredefinedSheetStyle(
+                            isPresented: $wrapper.isConfiguringCycle,
+                            isCompact: false
+                        ) {
+                            CycleActionConfigurationView(
+                                action: actionBinding,
+                                isPresented: $wrapper.isConfiguringCycle
+                            )
+                            .frame(width: 400)
+                        }
+                        .help("Customize what this action cycles through.")
+                    }
+                }
+            }
+            .font(.title3)
+            .foregroundStyle(isHovering ? .primary : .secondary)
+        }
+    }
+}
diff --git a/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionPickerView.swift b/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionPickerView.swift
new file mode 100644
index 00000000..72a42f84
--- /dev/null
+++ b/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionPickerView.swift	
@@ -0,0 +1,158 @@
+//
+//  RadialMenuActionPickerView.swift
+//  Loop
+//
+//  Created by Kai Azim on 2026-01-02.
+//
+
+import Defaults
+import SwiftUI
+
+struct RadialMenuActionPickerView: View {
+    @Default(.keybinds) private var keybinds
+
+    private let padding: CGFloat = 12
+
+    @State private var searchText = ""
+    @State private var searchResults: [RadialMenuAction.ActionType] = []
+
+    @Binding private var selection: RadialMenuAction.ActionType
+
+    private static let directionSections: [PickerSection<RadialMenuAction.ActionType>] = {
+        let windowDirections = PickerSection.windowDirections
+            .map { section in
+                PickerSection(
+                    section.title,
+                    section.items.map { RadialMenuAction.ActionType.custom(.init($0)) }
+                )
+            }
+
+        let moreSection = PickerSection(
+            String(localized: "More", comment: "Section header in the action picker of the Keybinds tab"),
+            [WindowDirection.custom, WindowDirection.cycle].map { RadialMenuAction.ActionType.custom(.init($0)) }
+        )
+
+        return windowDirections + [moreSection]
+    }()
+
+    private var keybindsSection: PickerSection<RadialMenuAction.ActionType> {
+        PickerSection(
+            "Your Keybinds",
+            keybinds.map { RadialMenuAction.ActionType.keybindReference($0.id) }
+        )
+    }
+
+    private var allSections: [PickerSection<RadialMenuAction.ActionType>] {
+        Self.directionSections + [keybindsSection]
+    }
+
+    private var allSectionItems: [RadialMenuAction.ActionType] {
+        allSections
+            .map(\.items)
+            .flatMap(\.self)
+    }
+
+    init(selection: Binding<RadialMenuAction.ActionType>) {
+        self._selection = selection
+    }
+
+    var body: some View {
+        VStack(spacing: 0) {
+            CustomTextField(
+                $searchText,
+                placeholder: .init(localized: "Search for a window action", defaultValue: "Search…")
+            )
+            .padding(padding)
+
+            Divider()
+
+            PickerList(
+                $selection,
+                $searchResults,
+                padding,
+                allSections
+            ) { item in
+                HStack(spacing: 8) {
+                    if let action = item.resolvedAction {
+                        HStack(spacing: 8) {
+                            IconView(action: action)
+
+                            Text(action.getName())
+                                .fontWeight(.regular)
+                                .lineLimit(1)
+                        }
+                    } else {
+                        Image(systemName: "bolt.horizontal.fill")
+                    }
+
+                    Spacer()
+
+                    if item.isKeybindReference {
+                        Image(systemName: "keyboard")
+                            .foregroundStyle(.secondary)
+                    }
+                }
+            }
+        }
+        .frame(width: 300, height: 300)
+        .onAppear {
+            searchText = ""
+            computeSearchResults()
+        }
+        .onDisappear {
+            searchText = ""
+        }
+        .onChange(of: searchText) { _ in
+            computeSearchResults()
+        }
+    }
+
+    private func computeSearchResults() {
+        guard !searchText.isEmpty else {
+            searchResults = []
+            return
+        }
+
+        let key = searchText.lowercased()
+
+        let matches = allSectionItems
+            .compactMap { item -> (RadialMenuAction.ActionType, Int)? in
+                guard let action = item.resolvedAction else { return nil }
+
+                if let score = fuzzyScore(action.getName(), key) {
+                    return (item, score)
+                }
+
+                return nil
+            }
+            .sorted { $0.1 < $1.1 }
+            .map(\.0)
+
+        searchResults = matches
+    }
+
+    private func fuzzyScore(_ text: String, _ pattern: String) -> Int? {
+        let text = text.lowercased()
+        let pattern = pattern.lowercased()
+
+        // Strong prefix match
+        if text.hasPrefix(pattern) { return 0 }
+
+        // Contains substring
+        if text.contains(pattern) { return 1 }
+
+        // Subsequence fuzzy match (letters appear in order)
+        var tIndex = text.startIndex
+        var pIndex = pattern.startIndex
+        while tIndex < text.endIndex, pIndex < pattern.endIndex {
+            if text[tIndex] == pattern[pIndex] {
+                pIndex = text.index(after: pIndex)
+            }
+            tIndex = text.index(after: tIndex)
+        }
+
+        if pIndex == pattern.endIndex { return 2 }
+
+        return nil
+    }
+}
diff --git a/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionsGuide.swift b/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionsGuide.swift
new file mode 100644
index 00000000..835a9f19
--- /dev/null
+++ b/Loop/Settings Window/Theming/Radial Menu/RadialMenuActionsGuide.swift	
@@ -0,0 +1,125 @@
+//
+//  RadialMenuActionsGuide.swift
+//  Loop
+//
+//  Created by Kai Azim on 2026-01-01.
+//
+
+import Defaults
+import Luminare
+import SwiftUI
+
+struct RadialMenuActionsGuide: View {
+    @EnvironmentObject private var windowModel: SettingsWindowManager
+    @ObservedObject private var accentColorController: AccentColorController = .shared
+    @Environment(\.luminareAnimation) private var luminareAnimation
+
+    @Default(.radialMenuActions) private var radialMenuActions
+
+    private var radialActions: [RadialMenuAction] {
+        Array(radialMenuActions.dropLast())
+    }
+
+    private var centerAction: RadialMenuAction {
+        radialMenuActions.last ?? .custom(.init(.noAction))
+    }
+
+    private var activeAction: WindowAction {
+        windowModel.previewedParentAction ?? windowModel.previewedAction
+    }
+
+    private var selectedColor: Color {
+        windowModel.isPreviewingUserSelection ? accentColorController.color1.opacity(0.6) : accentColorController.color2.opacity(0.3)
+    }
+
+    private var buttonShape: RoundedRectangle {
+        RoundedRectangle(cornerRadius: 12)
+    }
+
+    var body: some View {
+        ZStack {
+            if let centerResolved = centerAction.resolved {
+                actionButton(
+                    action: centerResolved,
+                    isActive: centerResolved == activeAction
+                ) {
+                    IconView(action: centerResolved)
+                }
+            } else {
+                actionButton(isActive: false) {
+                    Image(systemName: "bolt.horizontal.fill")
+                        .foregroundStyle(.secondary)
+                }
+            }
+
+            RadialLayout {
+                ForEach(Array(radialMenuActions.dropLast()), id: \.id) { action in
+                    if let resolved = action.resolved {
+                        actionButton(
+                            action: resolved,
+                            isActive: resolved == activeAction
+                        ) {
+                            IconView(action: resolved)
+                        }
+                    } else {
+                        actionButton(isActive: false) {
+                            Image(systemName: "bolt.horizontal.fill")
+                                .foregroundStyle(.secondary)
+                        }
+                    }
+                }
+            }
+        }
+        .compositingGroup()
+        .shadow(radius: 8)
+        .frame(width: 200, height: 200)
+        .animation(luminareAnimation, value: radialMenuActions)
+    }
+
+    @ViewBuilder
+    private func actionButton(
+        action: WindowAction? = nil,
+        isActive: Bool,
+        content: () -> some View
+    ) -> some View {
+        Button {
+            guard let action else {
+                return
+            }
+
+            if windowModel.previewedParentAction ?? windowModel.previewedAction == action {
+                windowModel.isPreviewingUserSelection.toggle()
+            } else {
+                windowModel.isPreviewingUserSelection = true
+            }
+
+            if windowModel.isPreviewingUserSelection {
+                windowModel.setPreviewedAction(to: action)
+            }
+        } label: {
+            ZStack {
+                if #available(macOS 26.0, *) {
+                    content()
+                        .frame(width: 30, height: 30)
+                        .glassEffect(
+                            .clear.tint(isActive ? selectedColor : nil),
+                            in: buttonShape
+                        )
+                } else {
+                    content()
+                        .frame(width: 30, height: 30)
+                }
+            }
+            .background {
+                VisualEffectView(material: .hudWindow, blendingMode: .behindWindow)
+                    .padding(0.5) // Fixes odd clipping behavior where slither of view is shown at top
+                    .clipShape(buttonShape)
+            }
+            .contentShape(.rect)
+        }
+        .buttonStyle(.plain)
+        .scaleEffect(isActive ? 1.05 : 0.95)
+        .disabled(action == nil)
+        .animation(luminareAnimation, value: isActive)
+    }
+}
diff --git a/Loop/Settings Window/Theming/Radial Menu/RadialMenuConfigurationView.swift b/Loop/Settings Window/Theming/Radial Menu/RadialMenuConfigurationView.swift
new file mode 100644
index 00000000..a556872c
--- /dev/null
+++ b/Loop/Settings Window/Theming/Radial Menu/RadialMenuConfigurationView.swift	
@@ -0,0 +1,147 @@
+//
+//  RadialMenuConfigurationView.swift
+//  Loop
+//
+//  Created by Kai Azim on 2024-04-19.
+//
+
+import Defaults
+import Luminare
+import SwiftUI
+
+struct RadialMenuConfigurationView: View {
+    @EnvironmentObject private var windowModel: SettingsWindowManager
+
+    @Default(.radialMenuVisibility) private var radialMenuVisibility
+    @Default(.radialMenuCornerRadius) private var radialMenuCornerRadius
+    @Default(.radialMenuThickness) private var radialMenuThickness
+    @Default(.enableRadialMenuCustomization) var enableRadialMenuCustomization
+    @Default(.radialMenuActions) private var radialMenuActions
+    @State private var selectedRadialMenuActions: Set<RadialMenuAction> = []
+
+    var body: some View {
+        LuminareSection {
+            LuminareToggle("Radial menu", isOn: $radialMenuVisibility)
+
+            if radialMenuVisibility {
+                LuminareSlider(
+                    "Corner radius",
+                    value: $radialMenuCornerRadius.doubleBinding,
+                    in: 30...50,
+                    format: .number.precision(.fractionLength(0...0)),
+                    clampsUpper: true,
+                    clampsLower: true,
+                    suffix: Text("px", comment: "Unit symbol: pixels")
+                )
+                .onChange(of: radialMenuCornerRadius) { _ in
+                    if radialMenuCornerRadius - 1 < radialMenuThickness {
+                        radialMenuThickness = radialMenuCornerRadius - 1
+                    }
+                }
+
+                LuminareSlider(
+                    "Thickness",
+                    value: $radialMenuThickness.doubleBinding,
+                    in: 10...35,
+                    format: .number.precision(.fractionLength(0...0)),
+                    clampsUpper: true,
+                    clampsLower: true,
+                    suffix: Text("px", comment: "Unit symbol: pixels")
+                )
+                .onChange(of: radialMenuThickness) { _ in
+                    if radialMenuThickness + 1 > radialMenuCornerRadius {
+                        radialMenuCornerRadius = radialMenuThickness + 1
+                    }
+                }
+            }
+        }
+        .animation(.smooth(duration: 0.25), value: radialMenuVisibility)
+
+        if enableRadialMenuCustomization {
+            LuminareSection(
+                String(localized: "Actions", comment: "Section header shown in settings"),
+                String(localized: "Left-click to step through cycle actions.", comment: "Section footer shown in settings")
+            ) {
+                HStack(spacing: 4) {
+                    Button("Add") {
+                        radialMenuActions.insert(.custom(.init(.noAction)), at: 0)
+                    }
+                    .luminareRoundingBehavior(topLeading: true)
+
+                    Button("Remove", role: .destructive) {
+                        radialMenuActions.removeAll(where: selectedRadialMenuActions.contains)
+                    }
+                    .luminareRoundingBehavior(topTrailing: true)
+                    .disabled(selectedRadialMenuActions.isEmpty)
+                    .keyboardShortcut(.delete)
+                }
+
+                LuminareList(
+                    items: $radialMenuActions,
+                    selection: $selectedRadialMenuActions,
+                    id: \.id
+                ) { action in
+                    RadialMenuActionItemView(
+                        action,
+                        moveUp: { moveAction(action.wrappedValue, down: false) },
+                        moveDown: { moveAction(action.wrappedValue, down: true) }
+                    )
+                } emptyView: {
+                    HStack {
+                        Spacer()
+                        VStack {
+                            Text("No radial menu actions")
+                                .font(.title3)
+                            Text("Press \"Add\" to add an action")
+                                .font(.caption)
+                        }
+                        Spacer()
+                    }
+                    .foregroundStyle(.secondary)
+                    .padding()
+                }
+                .luminareRoundingBehavior(bottom: true)
+                .onChange(of: selectedRadialMenuActions, perform: userSelectionChanged)
+                .onChange(of: windowModel.previewedParentAction ?? windowModel.previewedAction, perform: previewedActionChanged)
+                .onDisappear {
+                    windowModel.isPreviewingUserSelection = false
+                }
+            }
+        }
+    }
+
+    private func moveAction(_ action: RadialMenuAction, down: Bool) {
+        guard
+            let index = radialMenuActions.firstIndex(where: { $0.id == action.id })
+        else { return }
+
+        let newIndex = index + (down ? 1 : -1)
+        guard radialMenuActions.indices.contains(newIndex) else { return }
+
+        radialMenuActions.move(
+            fromOffsets: IndexSet(integer: index),
+            toOffset: newIndex > index ? newIndex + 1 : newIndex
+        )
+    }
+
+    private func userSelectionChanged(_ newValue: Set<RadialMenuAction>) {
+        if newValue.count == 1, let resolved = newValue.first?.resolved {
+            windowModel.isPreviewingUserSelection = true
+            windowModel.setPreviewedAction(to: resolved)
+        } else {
+            windowModel.isPreviewingUserSelection = false
+        }
+    }
+
+    private func previewedActionChanged(_ newAction: WindowAction) {
+        guard windowModel.isPreviewingUserSelection else {
+            return
+        }
+
+        if let match = radialMenuActions.first(where: { $0.associatedActionId == newAction.id }) {
+            selectedRadialMenuActions = [match]
+        } else {
+            selectedRadialMenuActions = []
+        }
+    }
+}
diff --git a/Loop/Settings Window/Theming/RadialMenuConfiguration.swift b/Loop/Settings Window/Theming/RadialMenuConfiguration.swift
deleted file mode 100644
index b7017a5b..00000000
--- a/Loop/Settings Window/Theming/RadialMenuConfiguration.swift	
+++ /dev/null
@@ -1,55 +0,0 @@
-//
-//  RadialMenuConfiguration.swift
-//  Loop
-//
-//  Created by Kai Azim on 2024-04-19.
-//
-
-import Defaults
-import Luminare
-import SwiftUI
-
-struct RadialMenuConfigurationView: View {
-    @Default(.radialMenuVisibility) private var radialMenuVisibility
-    @Default(.radialMenuCornerRadius) private var radialMenuCornerRadius
-    @Default(.radialMenuThickness) private var radialMenuThickness
-
-    var body: some View {
-        LuminareSection {
-            LuminareToggle("Radial menu", isOn: $radialMenuVisibility)
-
-            if radialMenuVisibility {
-                LuminareSlider(
-                    "Corner radius",
-                    value: $radialMenuCornerRadius.doubleBinding,
-                    in: 30...50,
-                    format: .number.precision(.fractionLength(0...0)),
-                    clampsUpper: true,
-                    clampsLower: true,
-                    suffix: Text("px", comment: "Unit symbol: pixels")
-                )
-                .onChange(of: radialMenuCornerRadius) { _ in
-                    if radialMenuCornerRadius - 1 < radialMenuThickness {
-                        radialMenuThickness = radialMenuCornerRadius - 1
-                    }
-                }
-
-                LuminareSlider(
-                    "Thickness",
-                    value: $radialMenuThickness.doubleBinding,
-                    in: 10...35,
-                    format: .number.precision(.fractionLength(0...0)),
-                    clampsUpper: true,
-                    clampsLower: true,
-                    suffix: Text("px", comment: "Unit symbol: pixels")
-                )
-                .onChange(of: radialMenuThickness) { _ in
-                    if radialMenuThickness + 1 > radialMenuCornerRadius {
-                        radialMenuCornerRadius = radialMenuThickness + 1
-                    }
-                }
-            }
-        }
-        .animation(.smooth(duration: 0.25), value: radialMenuVisibility)
-    }
-}
diff --git a/Loop/Stashing/StashManager.swift b/Loop/Stashing/StashManager.swift
index 0d370d57..6518b390 100644
--- a/Loop/Stashing/StashManager.swift
+++ b/Loop/Stashing/StashManager.swift
@@ -415,7 +415,7 @@ private extension StashManager {
 
             // Trying to store windowToStash in the same place as stashedWindow.
             // No need for frame comparaison, it will always overlap.
-            if stashedWindow.action.isSameManipulation(as: windowToStash.action), stashedWindow.screen.isSameScreen(windowToStash.screen) {
+            if stashedWindow.action.id == windowToStash.action.id, stashedWindow.screen.isSameScreen(windowToStash.screen) {
                 Log.info("Trying to stash a window in the same place as another one. Replacing…", category: .stashManager)
                 unstash(stashedWindow, resetFrame: true, resetFrameAnimated: animate)
             } else {
diff --git a/Loop/Stashing/StashedWindowStore.swift b/Loop/Stashing/StashedWindowStore.swift
index 4fc8209b..8e38bbc9 100644
--- a/Loop/Stashing/StashedWindowStore.swift
+++ b/Loop/Stashing/StashedWindowStore.swift
@@ -23,9 +23,7 @@ final class StashedWindowsStore {
         didSet { persistStashedWindows() }
     }
 
-    var revealed: Set<CGWindowID> = [] {
-        didSet { persistRevealedWindows() }
-    }
+    private(set) var revealed: Set<CGWindowID> = []
 
     /// Hold data from `Defaults[.stashManagerStashedWindows]` for windows that failed to be restored.
     private var failedToRestore: [CGWindowID: WindowAction] = [:]
@@ -34,7 +32,6 @@ final class StashedWindowsStore {
     // MARK: - Public methods
 
     func restore() {
-        restoreRevealedWindows()
         restoreStashedWindows()
     }
 
@@ -53,7 +50,7 @@ final class StashedWindowsStore {
     /// Return the stashed window that match the given `action` and `screen`
     func stashedWindow(for action: WindowAction, on screen: NSScreen) -> StashedWindow? {
         for stashedWindow in stashed.values {
-            if stashedWindow.action.isSameManipulation(as: action), stashedWindow.screen.isSameScreen(screen) {
+            if stashedWindow.action.id == action.id, stashedWindow.screen.isSameScreen(screen) {
                 return stashedWindow
             }
         }
@@ -62,10 +59,6 @@ final class StashedWindowsStore {
 
     // MARK: Private methods
 
-    func restoreRevealedWindows() {
-        revealed = Defaults[.stashManagerRevealedWindows]
-    }
-
     func restoreStashedWindows() {
         let windows = WindowUtility.windowList()
         let defaultStashedWindows = Defaults[.stashManagerStashedWindows]
@@ -130,10 +123,6 @@ final class StashedWindowsStore {
         return StashedWindow(window: window, screen: screen, action: action)
     }
 
-    func persistRevealedWindows() {
-        Defaults[.stashManagerRevealedWindows] = revealed
-    }
-
     func persistStashedWindows() {
         Defaults[.stashManagerStashedWindows] = stashed.mapValues(\.action)
     }
diff --git a/Loop/Settings Window/Settings/Keybinds/Item View/CustomTextField.swift b/Loop/Utilities/CustomTextField.swift
similarity index 92%
rename from Loop/Settings Window/Settings/Keybinds/Item View/CustomTextField.swift
rename to Loop/Utilities/CustomTextField.swift
index 42a5ddd8..0cae2196 100644
--- a/Loop/Settings Window/Settings/Keybinds/Item View/CustomTextField.swift	
+++ b/Loop/Utilities/CustomTextField.swift
@@ -12,7 +12,7 @@ struct CustomTextField: NSViewRepresentable {
     @Binding var text: String
     let placeholder: String
 
-    init(_ text: Binding<String>, _ placeholder: String = .init(localized: "Search for a window action", defaultValue: "Search…")) {
+    init(_ text: Binding<String>, placeholder: String) {
         self._text = text
         self.placeholder = placeholder
     }
diff --git a/Loop/Settings Window/Settings/Keybinds/Item View/PickerList.swift b/Loop/Utilities/PickerList.swift
similarity index 73%
rename from Loop/Settings Window/Settings/Keybinds/Item View/PickerList.swift
rename to Loop/Utilities/PickerList.swift
index 6fa9eec7..368ab6c7 100644
--- a/Loop/Settings Window/Settings/Keybinds/Item View/PickerList.swift	
+++ b/Loop/Utilities/PickerList.swift
@@ -205,3 +205,24 @@ struct PickerSection<V>: Identifiable, Hashable where V: Hashable, V: Identifiab
         self.items = items
     }
 }
+
+extension PickerSection where V == WindowDirection {
+    static var windowDirections: [PickerSection<WindowDirection>] {
+        [
+            .init(String(localized: "General", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.general),
+            .init(String(localized: "Halves", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.halves),
+            .init(String(localized: "Quarters", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.quarters),
+            .init(String(localized: "Horizontal Thirds", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.horizontalThirds),
+            .init(String(localized: "Vertical Thirds", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.verticalThirds),
+            .init(String(localized: "Horizontal Fourths", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.horizontalFourths),
+            .init(String(localized: "Screen Switching", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.screenSwitching),
+            .init(String(localized: "Size Adjustment", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.sizeAdjustment),
+            .init(String(localized: "Shrink", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.shrink),
+            .init(String(localized: "Grow", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.grow),
+            .init(String(localized: "Move", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.move),
+            .init(String(localized: "Focus", comment: "Section header in the action picker of the Keybinds tab"), WindowDirection.focus),
+            .init(String(localized: "Stash", comment: "Section header in the action picker of the Keybinds tab"), [WindowDirection.stash, WindowDirection.unstash]),
+            .init(String(localized: "Go Back", comment: "Section header in the action picker of the Keybinds tab"), [WindowDirection.initialFrame, WindowDirection.undo])
+        ]
+    }
+}
diff --git a/Loop/Window Action Indicators/Preview Window/LuminarePreviewView.swift b/Loop/Window Action Indicators/Preview Window/LuminarePreviewView.swift
index 6a7b12a2..698aa6c9 100644
--- a/Loop/Window Action Indicators/Preview Window/LuminarePreviewView.swift	
+++ b/Loop/Window Action Indicators/Preview Window/LuminarePreviewView.swift	
@@ -12,11 +12,10 @@ import SwiftUI
 struct LuminarePreviewView: View {
     @Environment(\.luminareAnimation) private var luminareAnimation
     @Environment(\.appearsActive) private var appearsActive
-    @ObservedObject var model: SettingsWindowManager = .shared
+    @EnvironmentObject private var windowModel: SettingsWindowManager
     @ObservedObject private var accentColorController: AccentColorController = .shared
 
     @State var actionRect: CGRect = .zero
-    @State private var scale: CGFloat = 1
 
     @Default(.previewPadding) var previewPadding
     @Default(.padding) var padding
@@ -52,23 +51,32 @@ struct LuminarePreviewView: View {
             .padding(previewPadding + previewBorderThickness / 2)
             .frame(width: actionRect.width, height: actionRect.height)
             .offset(x: actionRect.minX, y: actionRect.minY)
-            .scaleEffect(CGSize(width: scale, height: scale))
-            .onAppear {
-                actionRect = model.previewedAction.getFrame(window: nil, bounds: .init(origin: .zero, size: geo.size), isPreview: true)
-
-                withAnimation(
-                    .interpolatingSpring(
-                        duration: 0.2,
-                        bounce: 0.1,
-                        initialVelocity: 1 / 2
+            .opacity(actionRect.size.area == .zero ? 0 : 1)
+            .onChange(
+                of: windowModel.previewedAction,
+                initial: true
+            ) { newAction in
+                let newActionRect: CGRect = if newAction.willManipulateExistingWindowFrame {
+                    .zero
+                } else {
+                    newAction.getFrame(
+                        window: nil,
+                        bounds: .init(origin: .zero, size: geo.size),
+                        isPreview: true
                     )
-                ) {
-                    scale = 1
                 }
-            }
-            .onChange(of: model.previewedAction) { _ in
+
                 withAnimation(animationConfiguration.previewTimingFunctionSwiftUI) {
-                    actionRect = model.previewedAction.getFrame(window: nil, bounds: .init(origin: .zero, size: geo.size))
+                    if newActionRect.size.area == .zero {
+                        actionRect = .init(
+                            x: geo.size.width / 2,
+                            y: geo.size.height / 2,
+                            width: 0,
+                            height: 0
+                        )
+                    } else {
+                        actionRect = newActionRect
+                    }
                 }
             }
         }
diff --git a/Loop/Window Action Indicators/Preview Window/PreviewController.swift b/Loop/Window Action Indicators/Preview Window/PreviewController.swift
index 5d08363c..406dd55b 100644
--- a/Loop/Window Action Indicators/Preview Window/PreviewController.swift	
+++ b/Loop/Window Action Indicators/Preview Window/PreviewController.swift	
@@ -60,6 +60,11 @@ final class PreviewController {
         let window = windowController.window
         controller = nil
 
+        if window?.alphaValue == 0 {
+            windowController.close()
+            return
+        }
+
         let animationConfiguration = Defaults[.animationConfiguration]
         if let timingFunction = animationConfiguration.previewTimingFunction {
             window?.alphaValue = 1
diff --git a/Loop/Window Action Indicators/Radial Menu/RadialLayout.swift b/Loop/Window Action Indicators/Radial Menu/RadialLayout.swift
new file mode 100644
index 00000000..d2099d4a
--- /dev/null
+++ b/Loop/Window Action Indicators/Radial Menu/RadialLayout.swift	
@@ -0,0 +1,29 @@
+//
+//  RadialLayout.swift
+//  Loop
+//
+//  Created by Kai Azim on 2025-12-31.
+//
+
+import SwiftUI
+
+struct RadialLayout: Layout {
+    func sizeThatFits(proposal: ProposedViewSize, subviews _: Subviews, cache _: inout ()) -> CGSize {
+        proposal.replacingUnspecifiedDimensions()
+    }
+
+    func placeSubviews(in bounds: CGRect, proposal _: ProposedViewSize, subviews: Subviews, cache _: inout ()) {
+        let radius = min(bounds.size.width, bounds.size.height) / 2
+        let angle = Angle.degrees(360 / Double(subviews.count)).radians
+
+        for (index, subview) in subviews.enumerated() {
+            let viewSize = subview.sizeThatFits(.unspecified)
+
+            let xPos = cos(angle * Double(index) - .pi / 2) * (radius - viewSize.width / 2)
+            let yPos = sin(angle * Double(index) - .pi / 2) * (radius - viewSize.height / 2)
+
+            let point = CGPoint(x: bounds.midX + xPos, y: bounds.midY + yPos)
+            subview.place(at: point, anchor: .center, proposal: .unspecified)
+        }
+    }
+}
diff --git a/Loop/Window Action Indicators/Radial Menu/RadialMenuController.swift b/Loop/Window Action Indicators/Radial Menu/RadialMenuController.swift
index c8ecc4c1..b8eea381 100644
--- a/Loop/Window Action Indicators/Radial Menu/RadialMenuController.swift	
+++ b/Loop/Window Action Indicators/Radial Menu/RadialMenuController.swift	
@@ -16,7 +16,7 @@ final class RadialMenuController {
     func open(
         position: CGPoint,
         window: Window?,
-        startingAction: WindowAction?
+        startingAction: WindowAction
     ) {
         if let windowController = controller {
             windowController.window?.orderFrontRegardless()
diff --git a/Loop/Window Action Indicators/Radial Menu/RadialMenuView.swift b/Loop/Window Action Indicators/Radial Menu/RadialMenuView.swift
index 6c151e81..8984bbce 100644
--- a/Loop/Window Action Indicators/Radial Menu/RadialMenuView.swift	
+++ b/Loop/Window Action Indicators/Radial Menu/RadialMenuView.swift	
@@ -70,7 +70,7 @@ struct RadialMenuView: View {
         .shadow(radius: 10)
         .padding(20)
         .fixedSize()
-        .scaleEffect(viewModel.radialMenuScale)
+        .scaleEffect(viewModel.shouldFillRadialMenu ? 0.85 : 1.0)
         .animation(animationConfiguration.radialMenuSize, value: viewModel.currentAction)
         .animation(luminareAnimation, value: [accentColorController.color1, accentColorController.color2])
     }
@@ -79,24 +79,24 @@ struct RadialMenuView: View {
         ZStack {
             if viewModel.shouldFillRadialMenu {
                 Color.white
-            }
-
-            ZStack {
-                if radialMenuCornerRadius >= radialMenuSize / 2 - 2 {
-                    DirectionSelectorCircleSegment(
-                        angle: viewModel.angle,
-                        radialMenuSize: radialMenuSize
-                    )
-                } else {
-                    DirectionSelectorSquareSegment(
-                        angle: viewModel.angle,
-                        radialMenuCornerRadius: radialMenuCornerRadius,
-                        radialMenuThickness: radialMenuThickness
-                    )
+            } else {
+                ZStack {
+                    if radialMenuCornerRadius >= radialMenuSize / 2 - 2 {
+                        DirectionSelectorCircleSegment(
+                            angle: viewModel.angle,
+                            radialMenuSize: radialMenuSize
+                        )
+                    } else {
+                        DirectionSelectorSquareSegment(
+                            angle: viewModel.angle,
+                            radialMenuCornerRadius: radialMenuCornerRadius,
+                            radialMenuThickness: radialMenuThickness
+                        )
+                    }
                 }
+                .compositingGroup()
+                .opacity(viewModel.shouldHideDirectionSelector ? 0 : 1)
             }
-            .compositingGroup()
-            .opacity(viewModel.shouldHideDirectionSelector ? 0 : 1)
         }
         .frame(maxWidth: .infinity, maxHeight: .infinity)
     }
diff --git a/Loop/Window Action Indicators/Radial Menu/RadialMenuViewModel.swift b/Loop/Window Action Indicators/Radial Menu/RadialMenuViewModel.swift
index 9a4ca64f..a2c8396d 100644
--- a/Loop/Window Action Indicators/Radial Menu/RadialMenuViewModel.swift	
+++ b/Loop/Window Action Indicators/Radial Menu/RadialMenuViewModel.swift	
@@ -12,14 +12,17 @@ import SwiftUI
 /// By keeping the state separate, we are able to use the same `RadialMenuView` both in the app's settings, as well as in actual usage.
 final class RadialMenuViewModel: ObservableObject {
     @Published private(set) var angle: Double
-    @Published private(set) var currentAction: WindowAction?
+    @Published private(set) var currentAction: WindowAction
+
+    /// If a cycling action is chosen, this will represent the enclosing cycle action
+    @Published private(set) var parentAction: WindowAction?
 
     private var previousAction: WindowAction?
     private var window: Window?
     let previewMode: Bool
 
     init(
-        startingAction: WindowAction?,
+        startingAction: WindowAction,
         window: Window?,
         previewMode: Bool
     ) {
@@ -34,22 +37,50 @@ final class RadialMenuViewModel: ObservableObject {
         recomputeAngle()
     }
 
+    private var effectiveWindowAction: WindowAction {
+        parentAction ?? currentAction
+    }
+
+    private var radialMenuActions: [RadialMenuAction] {
+        RadialMenuAction.userConfiguredActions
+    }
+
+    private var directionalRadialMenuActions: [RadialMenuAction] {
+        radialMenuActions.dropLast()
+    }
+
+    private var centerRadialMenuAction: RadialMenuAction? {
+        radialMenuActions.last
+    }
+
     var shouldFillRadialMenu: Bool {
-        currentAction?.direction.shouldFillRadialMenu ?? false
+        // If the user has the center action selected, then fill the radial menu
+        if effectiveWindowAction.id == centerRadialMenuAction?.associatedActionId {
+            return true
+        }
+
+        guard !directionalRadialMenuActions.contains(where: { $0.associatedActionId == effectiveWindowAction.id }) else {
+            return false
+        }
+
+        // Otherwise, default to the action's settings
+        return effectiveWindowAction.direction.shouldFillRadialMenu
     }
 
     var shouldHideDirectionSelector: Bool {
-        currentAction?.direction.hasRadialMenuAngle != true || currentAction?.direction.isCustomizable == true
-    }
+        // If the current action is a user-set radial menu action, always show the direction selector
+        if radialMenuActions.contains(where: { $0.associatedActionId == effectiveWindowAction.id }) {
+            return false
+        }
 
-    var radialMenuScale: CGFloat {
-        currentAction?.direction == .maximize ? 0.85 : 1
+        // Otherwise, default to the action's settings
+        return currentAction.direction.hasRadialMenuAngle != true || currentAction.direction.isCustomizable == true
     }
 
     var radialMenuImage: Image? {
         if window == nil, !previewMode {
             return Image(systemName: "exclamationmark.triangle")
-        } else if let image = currentAction?.image {
+        } else if let image = currentAction.image {
             let image = image.withSymbolConfiguration(.init(pointSize: 20, weight: .bold)) ?? image
             return Image(nsImage: image)
         } else {
@@ -61,26 +92,43 @@ final class RadialMenuViewModel: ObservableObject {
         window = newWindow
     }
 
-    func setAction(to action: WindowAction) {
+    func setAction(to action: WindowAction, parent: WindowAction? = nil) {
         previousAction = currentAction
         currentAction = action
+        parentAction = parent
 
         recomputeAngle()
     }
 
     func recomputeAngle() {
-        if let target = currentAction?.radialMenuAngle(window: window) {
-            let closestAngle: Angle = .degrees(angle).angleDifference(to: target)
+        guard let targetAngle = calculateTargetAngle() else { return }
 
-            let previousActionHadAngle = previousAction?.direction.hasRadialMenuAngle ?? false
-            let animate: Bool = abs(closestAngle.degrees) < 179 && previousActionHadAngle
+        let closestAngle = Angle.degrees(angle).angleDifference(to: targetAngle)
+        let shouldAnimate = shouldAnimateTransition(closestAngle: closestAngle)
 
-            let defaultAnimation = AnimationConfiguration.radialMenuAngle
-            let noAnimation = Animation.linear(duration: 0)
+        withAnimation(shouldAnimate ? AnimationConfiguration.radialMenuAngle : .linear(duration: 0)) {
+            angle += closestAngle.degrees
+        }
+    }
 
-            withAnimation(animate ? defaultAnimation : noAnimation) {
-                angle += closestAngle.degrees
-            }
+    private func calculateTargetAngle() -> Angle? {
+        // Check directional radial menu actions first
+        if let index = directionalRadialMenuActions.firstIndex(where: { $0.associatedActionId == effectiveWindowAction.id }) {
+            let actionAngleSpan = 360.0 / CGFloat(directionalRadialMenuActions.count)
+            return Angle(degrees: CGFloat(index) * actionAngleSpan - 90)
         }
+
+        // Otherwise, default to the current action's radial menu angle
+        return currentAction.radialMenuAngle(window: window)
+    }
+
+    private func shouldAnimateTransition(closestAngle: Angle) -> Bool {
+        guard abs(closestAngle.degrees) < 179 else { return false }
+
+        if let previousAction {
+            return directionalRadialMenuActions.contains(where: { $0.associatedActionId == previousAction.id }) || previousAction.direction.hasRadialMenuAngle
+        }
+
+        return false
     }
 }
diff --git a/Loop/Window Management/Window Action/RadialMenuAction.swift b/Loop/Window Management/Window Action/RadialMenuAction.swift
new file mode 100644
index 00000000..f31d3173
--- /dev/null
+++ b/Loop/Window Management/Window Action/RadialMenuAction.swift	
@@ -0,0 +1,125 @@
+//
+//  RadialMenuAction.swift
+//  Loop
+//
+//  Created by Kai Azim on 2025-11-11.
+//
+
+import Defaults
+import Foundation
+
+struct RadialMenuAction: Identifiable, Codable, Hashable, Defaults.Serializable {
+    let id: UUID
+    var type: ActionType
+
+    enum ActionType: Identifiable, Codable, Hashable {
+        case custom(WindowAction)
+        case keybindReference(UUID)
+
+        var id: UUID {
+            switch self {
+            case let .custom(windowAction):
+                windowAction.id
+            case let .keybindReference(id):
+                id
+            }
+        }
+
+        var resolvedAction: WindowAction? {
+            switch self {
+            case let .custom(windowAction):
+                windowAction
+            case let .keybindReference(id):
+                if let action = Defaults[.keybinds].first(where: { $0.id == id }) {
+                    action
+                } else {
+                    nil
+                }
+            }
+        }
+
+        var isKeybindReference: Bool {
+            switch self {
+            case .custom:
+                false
+            case .keybindReference:
+                true
+            }
+        }
+    }
+
+    private init(id: UUID, type: ActionType) {
+        self.id = id
+        self.type = type
+    }
+
+    static func custom(_ action: WindowAction) -> Self {
+        self.init(
+            id: .init(),
+            type: .custom(action)
+        )
+    }
+
+    static func keybindReference(_ id: UUID) -> Self {
+        self.init(
+            id: .init(),
+            type: .keybindReference(id)
+        )
+    }
+
+    // MARK: Computed Helpers
+
+    var associatedActionId: UUID {
+        type.id
+    }
+
+    var resolved: WindowAction? {
+        type.resolvedAction
+    }
+}
+
+extension RadialMenuAction {
+    static let defaultRadialMenuActions: [RadialMenuAction] = [
+        .custom(
+            WindowAction(
+                .init(localized: "Top Cycle"),
+                cycle: [.init(.topHalf), .init(.topThird), .init(.topTwoThirds)]
+            )
+        ),
+        .custom(WindowAction(.topRightQuarter)),
+        .custom(
+            WindowAction(
+                .init(localized: "Right Cycle"),
+                cycle: [.init(.rightHalf), .init(.rightThird), .init(.rightTwoThirds)]
+            )
+        ),
+        .custom(WindowAction(.bottomRightQuarter)),
+        .custom(
+            WindowAction(
+                .init(localized: "Bottom Cycle"),
+                cycle: [.init(.bottomHalf), .init(.bottomThird), .init(.bottomTwoThirds)]
+            )
+        ),
+        .custom(WindowAction(.bottomLeftQuarter)),
+        .custom(
+            WindowAction(
+                .init(localized: "Left Cycle"),
+                cycle: [.init(.leftHalf), .init(.leftThird), .init(.leftTwoThirds)]
+            )
+        ),
+        .custom(WindowAction(.topLeftQuarter)),
+        .custom(
+            WindowAction(
+                "\(WindowDirection.maximize.name) + \(WindowDirection.macOSCenter.name)",
+                cycle: [
+                    .init(.maximize),
+                    .init(.macOSCenter)
+                ]
+            )
+        )
+    ]
+
+    static var userConfiguredActions: [RadialMenuAction] {
+        Defaults[.enableRadialMenuCustomization] ? Defaults[.radialMenuActions] : defaultRadialMenuActions
+    }
+}
diff --git a/Loop/Window Management/Window Action/RadialMenuWindowAction.swift b/Loop/Window Management/Window Action/RadialMenuWindowAction.swift
deleted file mode 100644
index 4795fd8f..00000000
--- a/Loop/Window Management/Window Action/RadialMenuWindowAction.swift	
+++ /dev/null
@@ -1,26 +0,0 @@
-//
-//  RadialMenuWindowAction.swift
-//  Loop
-//
-//  Created by Kai Azim on 2025-11-11.
-//
-
-import Defaults
-import Foundation
-
-enum RadialMenuWindowAction: Codable, Defaults.Serializable {
-    case custom(WindowAction)
-    case keybindReference(UUID)
-
-    static let defaultRadialMenuActions: [RadialMenuWindowAction] = [
-        .custom(.init([.init(.maximize), .init(.macOSCenter)])),
-        .custom(.init([.init(.rightHalf), .init(.rightThird), .init(.rightTwoThirds)])),
-        .custom(.init(.bottomRightQuarter)),
-        .custom(.init([.init(.bottomHalf), .init(.bottomThird), .init(.bottomTwoThirds)])),
-        .custom(.init(.bottomLeftQuarter)),
-        .custom(.init([.init(.leftHalf), .init(.leftThird), .init(.leftTwoThirds)])),
-        .custom(.init(.topLeftQuarter)),
-        .custom(.init([.init(.topHalf), .init(.topThird), .init(.topTwoThirds)])),
-        .custom(.init(.topRightQuarter))
-    ]
-}
diff --git a/Loop/Window Management/Window Action/WindowAction+Image.swift b/Loop/Window Management/Window Action/WindowAction+Image.swift
index 6298a7da..cae4ce16 100644
--- a/Loop/Window Management/Window Action/WindowAction+Image.swift	
+++ b/Loop/Window Management/Window Action/WindowAction+Image.swift	
@@ -11,6 +11,8 @@ import SwiftUI
 extension WindowAction {
     var image: NSImage? {
         switch direction {
+        case .noAction:
+            NSImage(systemSymbolName: "questionmark", accessibilityDescription: nil)
         case .undo:
             NSImage(systemSymbolName: "arrow.uturn.backward", accessibilityDescription: nil)
         case .initialFrame:
@@ -152,7 +154,7 @@ final class IconRenderView: NSView {
         to action: WindowAction,
         animated: Bool
     ) {
-        guard !action.isSameManipulation(as: currentAction) else { return }
+        guard action.id != currentAction.id else { return }
         currentAction = action
         updatePath(duration: animated ? 0.2 : 0.0)
     }
diff --git a/Loop/Window Management/Window Action/WindowAction.swift b/Loop/Window Management/Window Action/WindowAction.swift
index 3ce452fc..fefd40a1 100644
--- a/Loop/Window Management/Window Action/WindowAction.swift	
+++ b/Loop/Window Management/Window Action/WindowAction.swift	
@@ -13,7 +13,8 @@ import SwiftUI
 ///
 /// Common actions, such as right half, or bottom right quarter, are represented by `WindowDirection` enum, while user-made actions, such as custom frames and cycles are speciied by this struct.
 struct WindowAction: Codable, Identifiable, Hashable, Equatable, Defaults.Serializable {
-    private(set) var id: UUID = .init()
+    private(set) var id: UUID
+    private static var sharedNoSelectionId: UUID = .init()
 
     /// Initializes a `WindowAction` with the specified parameters. Only to be used when decoding from JSON.
     /// - Parameters:
@@ -61,6 +62,12 @@ struct WindowAction: Codable, Identifiable, Hashable, Equatable, Defaults.Serial
     /// Initializes a `WindowAction` with the specified direction and an empty keybind.
     /// - Parameter direction: the direction of the window action.
     init(_ direction: WindowDirection, keybind: Set<CGKeyCode> = []) {
+        if direction == .noSelection {
+            self.id = Self.sharedNoSelectionId
+        } else {
+            self.id = UUID()
+        }
+
         self.direction = direction
         self.keybind = keybind
     }
@@ -71,6 +78,7 @@ struct WindowAction: Codable, Identifiable, Hashable, Equatable, Defaults.Serial
     ///   - cycle: the cycle of window actions. This is an array of `WindowAction` that will be cycled through when the action is triggered.
     ///   - keybind: the keybinds associated with this action.
     init(_ name: String? = nil, cycle: [WindowAction], keybind: Set<CGKeyCode> = []) {
+        self.id = UUID()
         self.direction = .cycle
         self.name = name
         self.cycle = cycle
@@ -103,32 +111,6 @@ struct WindowAction: Codable, Identifiable, Hashable, Equatable, Defaults.Serial
 
     // MARK: - Methods
 
-    /// Determines if one action is equivalent to another, ignore all properties that are not related to resizing or moving the window.
-    /// - Parameter other: the other `WindowAction` to compare against.
-    /// - Returns: `true` if the two actions are equivalent in terms of resizing or moving the window, otherwise `false`.
-    func isSameManipulation(as other: WindowAction) -> Bool {
-        let commonID = UUID()
-
-        /// Removes ID, keybind and name. This is useful when checking for equality between an otherwise identical keybind and radial menu action.
-        func stripNonResizingProperties(of action: WindowAction) -> WindowAction {
-            var strippedAction = action
-            strippedAction.id = commonID
-            strippedAction.keybind = []
-            strippedAction.name = nil
-
-            if let cycle = action.cycle {
-                strippedAction.cycle = cycle.map { stripNonResizingProperties(of: $0) }
-            }
-
-            return strippedAction
-        }
-
-        let modifiedSelf = stripNonResizingProperties(of: self)
-        let modifiedOther = stripNonResizingProperties(of: other)
-
-        return modifiedSelf == modifiedOther
-    }
-
     /// Retrieves the name of the action, either from the `name` property or from the `direction` enum.
     /// - Returns: the name of the action.
     func getName() -> String {
@@ -138,7 +120,7 @@ struct WindowAction: Codable, Identifiable, Hashable, Equatable, Defaults.Serial
             result = if let name, !name.isEmpty {
                 name
             } else {
-                .init(localized: .init("Custom Keybind", defaultValue: "Custom Keybind"))
+                .init(localized: .init("Custom Action", defaultValue: "Custom Action"))
             }
         } else if direction == .stash {
             result = if let name, !name.isEmpty {
@@ -216,7 +198,7 @@ struct WindowAction: Codable, Identifiable, Hashable, Equatable, Defaults.Serial
         let frame = CGRect(origin: .zero, size: .init(width: 1, height: 1))
         let targetWindowFrame = getFrame(window: window, bounds: frame, disablePadding: true)
         let angle = frame.center.angle(to: targetWindowFrame.center)
-        let result: Angle = .radians(angle) * -1
+        let result: Angle = angle * -1
 
         return result.normalized()
     }
@@ -230,7 +212,7 @@ struct WindowAction: Codable, Identifiable, Hashable, Equatable, Defaults.Serial
     ///   - isPreview: ensures that when manipulating the preview window, the last target frame does not affect the actual resizing of the window.
     /// - Returns: the calculated frame for the specified window action.
     func getFrame(window: Window?, bounds: CGRect, disablePadding: Bool = false, screen: NSScreen? = nil, isPreview: Bool = false) -> CGRect {
-        let noFrameActions: [WindowDirection] = [.noAction, .cycle, .minimize, .hide]
+        let noFrameActions: [WindowDirection] = [.noAction, .noSelection, .cycle, .minimize, .hide]
         guard !noFrameActions.contains(direction), !direction.willFocusWindow else {
             return NSRect(origin: bounds.center, size: .zero)
         }
@@ -609,7 +591,6 @@ extension WindowAction {
     /// - Returns: the adjusted frame after applying the size adjustment based on the direction and bounds.
     private func calculateSizeAdjustment(_ frameToResizeFrom: CGRect, _ bounds: CGRect) -> CGRect {
         var result = frameToResizeFrom
-        let totalBounds: Edge.Set = [.top, .bottom, .leading, .trailing]
         let step = Defaults[.sizeIncrement] * ((direction == .larger || direction.willGrow) ? -1 : 1)
 
         let padding = PaddingSettings.padding
@@ -621,20 +602,24 @@ extension WindowAction {
 
         if LoopManager.sidesToAdjust == nil {
             let edgesTouchingBounds = frameToResizeFrom.getEdgesTouchingBounds(bounds)
-            LoopManager.sidesToAdjust = totalBounds.subtracting(edgesTouchingBounds)
+            LoopManager.sidesToAdjust = .all.subtracting(edgesTouchingBounds)
         }
 
         if let edgesToInset = LoopManager.sidesToAdjust {
-            if edgesToInset.isEmpty || edgesToInset.contains(totalBounds) {
-                result = result.inset(
-                    by: step,
-                    minSize: .init(
-                        width: minWidth,
-                        height: minHeight
+            if edgesToInset.isEmpty || edgesToInset.contains(.all) {
+                result = result
+                    .inset(
+                        by: step,
+                        minSize: .init(
+                            width: minWidth,
+                            height: minHeight
+                        )
                     )
-                )
+                    .intersection(bounds)
             } else {
-                result = result.padding(edgesToInset, step)
+                result = result
+                    .padding(edgesToInset, step)
+                    .intersection(bounds)
 
                 if result.width < minWidth {
                     result.size.width = minWidth
diff --git a/Loop/Window Management/Window Action/WindowDirection+LocalizedString.swift b/Loop/Window Management/Window Action/WindowDirection+LocalizedString.swift
index 38265762..188432b3 100644
--- a/Loop/Window Management/Window Action/WindowDirection+LocalizedString.swift	
+++ b/Loop/Window Management/Window Action/WindowDirection+LocalizedString.swift	
@@ -18,7 +18,7 @@ extension WindowDirection {
 
     var name: String {
         switch self {
-        case .noAction:
+        case .noAction, .noSelection:
             String(localized: "No Action", comment: "Window action: no selection")
         case .maximize:
             String(localized: "Maximize", comment: "Window action")
diff --git a/Loop/Window Management/Window Action/WindowDirection.swift b/Loop/Window Management/Window Action/WindowDirection.swift
index 5af27793..d9e27027 100644
--- a/Loop/Window Management/Window Action/WindowDirection.swift	
+++ b/Loop/Window Management/Window Action/WindowDirection.swift	
@@ -12,8 +12,13 @@ import SwiftUI
 enum WindowDirection: String, CaseIterable, Identifiable, Codable {
     var id: Self { self }
 
+    // "Empty" actions.
+    /// `noAction` is explicitly chosen or user-bound.
+    /// `noSelection` is the default state before any radial menu selection is made.
+    case noAction = "NoAction", noSelection = "NoSelection"
+
     // General Actions
-    case noAction = "NoAction", maximize = "Maximize", almostMaximize = "AlmostMaximize", fullscreen = "Fullscreen"
+    case maximize = "Maximize", almostMaximize = "AlmostMaximize", fullscreen = "Fullscreen"
     case maximizeHeight = "MaximizeHeight", maximizeWidth = "MaximizeWidth"
     case undo = "Undo", initialFrame = "InitialFrame", hide = "Hide", minimize = "Minimize", minimizeOthers = "MinimizeOthers"
     case macOSCenter = "MacOSCenter", center = "Center"
@@ -92,7 +97,7 @@ enum WindowDirection: String, CaseIterable, Identifiable, Codable {
     var isCustomizable: Bool { [.custom, .stash].contains(self) }
 
     var hasRadialMenuAngle: Bool {
-        let noAngleActions: [WindowDirection] = [.noAction, .minimize, .minimizeOthers, .hide, .initialFrame, .undo, .cycle]
+        let noAngleActions: [WindowDirection] = [.noAction, .noSelection, .minimize, .minimizeOthers, .hide, .initialFrame, .undo, .cycle]
         return !(noAngleActions.contains(self) || willChangeScreen || willAdjustSize || willShrink || willGrow || willMove || willFocusWindow || willMaximize || willCenter)
     }
 
@@ -138,20 +143,6 @@ enum WindowDirection: String, CaseIterable, Identifiable, Codable {
         }
     }
 
-    var nextPreviewDirection: WindowDirection {
-        switch self {
-        case .topHalf: .topRightQuarter
-        case .topRightQuarter: .rightHalf
-        case .rightHalf: .bottomRightQuarter
-        case .bottomRightQuarter: .bottomHalf
-        case .bottomHalf: .bottomLeftQuarter
-        case .bottomLeftQuarter: .leftHalf
-        case .leftHalf: .topLeftQuarter
-        case .topLeftQuarter: .maximize
-        default: .topHalf
-        }
-    }
-
     var focusDirection: NavigationDirection? {
         switch self {
         case .focusLeft: .left
diff --git a/Loop/Window Management/Window Manipulation/WindowEngine.swift b/Loop/Window Management/Window Manipulation/WindowEngine.swift
index 1813a758..a6176e30 100644
--- a/Loop/Window Management/Window Manipulation/WindowEngine.swift	
+++ b/Loop/Window Management/Window Manipulation/WindowEngine.swift	
@@ -23,7 +23,7 @@ enum WindowEngine {
         on screen: NSScreen,
         shouldRecord: Bool = true
     ) {
-        guard action.direction != .noAction, !action.direction.willFocusWindow else { return }
+        guard action.direction != .noAction, action.direction != .noSelection, !action.direction.willFocusWindow else { return }
 
         let willChangeScreens = ScreenUtility.screenContaining(window) != screen
 
@@ -74,47 +74,45 @@ enum WindowEngine {
             if !Defaults[.previewVisibility] {
                 LoopManager.lastTargetFrame = window.frame
             }
-
-            return
-        }
-
-        // Otherwise, we obviously need to disable fullscreen to resize the window
-        window.fullscreen = false
-
-        // Calculate the target frame
-        let targetFrame: CGRect = action.getFrame(
-            window: window,
-            bounds: screen.safeScreenFrame,
-            screen: screen
-        )
-        Log.info("Target window frame: \(targetFrame.debugDescription)", category: .windowEngine)
-
-        // If the action is undo, remove the last action from the window records.
-        if action.direction == .undo {
-            WindowRecords.removeLastAction(for: window)
-        }
-
-        // If the window is one of Loop's windows, resize it using the actual NSWindow, preventing crashes
-        if window.nsRunningApplication?.bundleIdentifier == Bundle.main.bundleIdentifier {
-            resizeOwnWindow(targetFrame: targetFrame)
         } else {
-            let shouldAnimate = shouldAnimateResize(
-                for: window,
-                willChangeScreens: willChangeScreens
-            )
-            resizeWindow(
-                window,
-                targetFrame: targetFrame,
-                screen: screen,
-                willChangeScreens: willChangeScreens,
-                ignorePadding: action.direction.willMove,
-                animate: shouldAnimate
+            // Otherwise, we obviously need to disable fullscreen to resize the window
+            window.fullscreen = false
+
+            // Calculate the target frame
+            let targetFrame: CGRect = action.getFrame(
+                window: window,
+                bounds: screen.safeScreenFrame,
+                screen: screen
             )
-        }
+            Log.info("Target window frame: \(targetFrame.debugDescription)", category: .windowEngine)
 
-        // Move cursor to center of window if user has enabled it
-        if Defaults[.moveCursorWithWindow] {
-            CGWarpMouseCursorPosition(targetFrame.center)
+            // If the action is undo, remove the last action from the window records.
+            if action.direction == .undo {
+                WindowRecords.removeLastAction(for: window)
+            }
+
+            // If the window is one of Loop's windows, resize it using the actual NSWindow, preventing crashes
+            if window.nsRunningApplication?.bundleIdentifier == Bundle.main.bundleIdentifier {
+                resizeOwnWindow(targetFrame: targetFrame)
+            } else {
+                let shouldAnimate = shouldAnimateResize(
+                    for: window,
+                    willChangeScreens: willChangeScreens
+                )
+                resizeWindow(
+                    window,
+                    targetFrame: targetFrame,
+                    screen: screen,
+                    willChangeScreens: willChangeScreens,
+                    ignorePadding: action.direction.willMove,
+                    animate: shouldAnimate
+                )
+            }
+
+            // Move cursor to center of window if user has enabled it
+            if Defaults[.moveCursorWithWindow] {
+                CGWarpMouseCursorPosition(targetFrame.center)
+            }
         }
 
         StashManager.shared.onWindowResized(