diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 85010bda..0b6d34c8 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -25,11 +25,9 @@ jobs:
   test:
     strategy:
       matrix:
-        python-version: ["3.8", "3.9", "3.10", "3.11", "3.12", "3.13", "3.14"]
+        python-version: ["3.9", "3.10", "3.11", "3.12", "3.13", "3.14"]
         pydantic-version: ["v2"]
         include:
-          - python-version: "3.8"
-            pydantic-version: "v1"
           - python-version: "3.9"
             pydantic-version: "v1"
           - python-version: "3.10"
diff --git a/.python-version b/.python-version
index cc1923a4..bd28b9c5 100644
--- a/.python-version
+++ b/.python-version
@@ -1 +1 @@
-3.8
+3.9
diff --git a/pyproject.toml b/pyproject.toml
index 2d0c946a..066b85e0 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -3,7 +3,7 @@ name = "fastapi-cloud-cli"
 dynamic = ["version"]
 description = "Deploy and manage FastAPI Cloud apps from the command line 🚀"
 authors = [{ name = "Patrick Arminio", email = "patrick@fastapilabs.com" }]
-requires-python = ">=3.8"
+requires-python = ">=3.9"
 readme = "README.md"
 license = { text = "MIT" }
 classifiers = [
@@ -22,7 +22,6 @@ classifiers = [
     "Intended Audience :: Developers",
     "License :: OSI Approved :: MIT License",
     "Programming Language :: Python :: 3 :: Only",
-    "Programming Language :: Python :: 3.8",
     "Programming Language :: Python :: 3.9",
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
diff --git a/src/fastapi_cloud_cli/commands/deploy.py b/src/fastapi_cloud_cli/commands/deploy.py
index e9c3f6ee..b67e18b6 100644
--- a/src/fastapi_cloud_cli/commands/deploy.py
+++ b/src/fastapi_cloud_cli/commands/deploy.py
@@ -7,7 +7,7 @@
 from itertools import cycle
 from pathlib import Path
 from textwrap import dedent
-from typing import Any, Dict, List, Optional, Union
+from typing import Annotated, Any, Optional, Union
 
 import fastar
 import rignore
@@ -17,7 +17,6 @@
 from rich.text import Text
 from rich_toolkit import RichToolkit
 from rich_toolkit.menu import Option
-from typing_extensions import Annotated
 
 from fastapi_cloud_cli.commands.login import login
 from fastapi_cloud_cli.utils.api import APIClient, BuildLogError, TooManyRetriesError
@@ -102,7 +101,7 @@ class Team(BaseModel):
     name: str
 
 
-def _get_teams() -> List[Team]:
+def _get_teams() -> list[Team]:
     with APIClient() as client:
         response = client.get("/teams/")
         response.raise_for_status()
@@ -184,7 +183,7 @@ def _create_deployment(app_id: str) -> CreateDeploymentResponse:
 
 class RequestUploadResponse(BaseModel):
     url: str
-    fields: Dict[str, str]
+    fields: dict[str, str]
 
 
 def _upload_deployment(deployment_id: str, archive_path: Path) -> None:
@@ -242,7 +241,7 @@ def _get_app(app_slug: str) -> Optional[AppResponse]:
     return model_validate(AppResponse, data)
 
 
-def _get_apps(team_id: str) -> List[AppResponse]:
+def _get_apps(team_id: str) -> list[AppResponse]:
     with APIClient() as client:
         response = client.get("/apps/", params={"team_id": team_id})
         response.raise_for_status()
@@ -363,9 +362,12 @@ def _wait_for_deployment(
 
     last_message_changed_at = time.monotonic()
 
-    with toolkit.progress(
-        next(messages), inline_logs=True, lines_to_show=20
-    ) as progress, APIClient() as client:
+    with (
+        toolkit.progress(
+            next(messages), inline_logs=True, lines_to_show=20
+        ) as progress,
+        APIClient() as client,
+    ):
         try:
             for log in client.stream_build_logs(deployment.id):
                 time_elapsed = time.monotonic() - started_at
@@ -609,9 +611,10 @@ def deploy(
             archive_path = Path(temp_dir) / "archive.tar"
             archive(path or Path.cwd(), archive_path)
 
-            with toolkit.progress(
-                title="Creating deployment"
-            ) as progress, handle_http_errors(progress):
+            with (
+                toolkit.progress(title="Creating deployment") as progress,
+                handle_http_errors(progress),
+            ):
                 logger.debug("Creating deployment for app: %s", app.id)
                 deployment = _create_deployment(app.id)
 
diff --git a/src/fastapi_cloud_cli/commands/env.py b/src/fastapi_cloud_cli/commands/env.py
index 613c49f3..1f81e131 100644
--- a/src/fastapi_cloud_cli/commands/env.py
+++ b/src/fastapi_cloud_cli/commands/env.py
@@ -1,10 +1,9 @@
 import logging
 from pathlib import Path
-from typing import Any, List, Union
+from typing import Annotated, Any, Union
 
 import typer
 from pydantic import BaseModel
-from typing_extensions import Annotated
 
 from fastapi_cloud_cli.utils.api import APIClient
 from fastapi_cloud_cli.utils.apps import get_app_config
@@ -22,7 +21,7 @@ class EnvironmentVariable(BaseModel):
 
 
 class EnvironmentVariableResponse(BaseModel):
-    data: List[EnvironmentVariable]
+    data: list[EnvironmentVariable]
 
 
 def _get_environment_variables(app_id: str) -> EnvironmentVariableResponse:
diff --git a/src/fastapi_cloud_cli/utils/api.py b/src/fastapi_cloud_cli/utils/api.py
index 5c817039..5e64c60a 100644
--- a/src/fastapi_cloud_cli/utils/api.py
+++ b/src/fastapi_cloud_cli/utils/api.py
@@ -1,12 +1,13 @@
 import json
 import logging
 import time
+from collections.abc import Generator
 from contextlib import contextmanager
 from datetime import timedelta
 from functools import wraps
 from typing import (
+    Annotated,
     Callable,
-    Generator,
     Literal,
     Optional,
     TypeVar,
@@ -15,7 +16,7 @@
 
 import httpx
 from pydantic import BaseModel, Field, ValidationError
-from typing_extensions import Annotated, ParamSpec
+from typing_extensions import ParamSpec
 
 from fastapi_cloud_cli import __version__
 from fastapi_cloud_cli.config import Settings
diff --git a/src/fastapi_cloud_cli/utils/cli.py b/src/fastapi_cloud_cli/utils/cli.py
index 2e798b57..5d815e92 100644
--- a/src/fastapi_cloud_cli/utils/cli.py
+++ b/src/fastapi_cloud_cli/utils/cli.py
@@ -1,6 +1,7 @@
 import contextlib
 import logging
-from typing import Any, Dict, Generator, List, Optional, Tuple
+from collections.abc import Generator
+from typing import Any, Optional
 
 import typer
 from httpx import HTTPError, HTTPStatusError, ReadTimeout
@@ -18,10 +19,10 @@ def __init__(self, tag_width: int = 11):
 
     def _get_tag_segments(
         self,
-        metadata: Dict[str, Any],
+        metadata: dict[str, Any],
         is_animated: bool = False,
         done: bool = False,
-    ) -> Tuple[List[Segment], int]:
+    ) -> tuple[list[Segment], int]:
         if not is_animated:
             return super()._get_tag_segments(metadata, is_animated, done)
 
diff --git a/src/fastapi_cloud_cli/utils/pydantic_compat.py b/src/fastapi_cloud_cli/utils/pydantic_compat.py
index 0e9d9a57..424fbfec 100644
--- a/src/fastapi_cloud_cli/utils/pydantic_compat.py
+++ b/src/fastapi_cloud_cli/utils/pydantic_compat.py
@@ -1,4 +1,4 @@
-from typing import Any, Dict, Generic, Type, TypeVar
+from typing import Any, Generic, TypeVar
 
 from pydantic import BaseModel
 from pydantic.version import VERSION as PYDANTIC_VERSION
@@ -11,21 +11,21 @@
 Model = TypeVar("Model", bound=BaseModel)
 
 
-def model_validate(model_class: Type[Model], data: Dict[Any, Any]) -> Model:
+def model_validate(model_class: type[Model], data: dict[Any, Any]) -> Model:
     if PYDANTIC_V2:
         return model_class.model_validate(data)  # type: ignore[no-any-return, unused-ignore, attr-defined]
     else:
         return model_class.parse_obj(data)  # type: ignore[no-any-return, unused-ignore, attr-defined]
 
 
-def model_validate_json(model_class: Type[Model], data: str) -> Model:
+def model_validate_json(model_class: type[Model], data: str) -> Model:
     if PYDANTIC_V2:
         return model_class.model_validate_json(data)  # type: ignore[no-any-return, unused-ignore, attr-defined]
     else:
         return model_class.parse_raw(data)  # type: ignore[no-any-return, unused-ignore, attr-defined]
 
 
-def model_dump(obj: BaseModel, **kwargs: Any) -> Dict[Any, Any]:
+def model_dump(obj: BaseModel, **kwargs: Any) -> dict[Any, Any]:
     if PYDANTIC_V2:
         return obj.model_dump(**kwargs)  # type: ignore[no-any-return, unused-ignore, attr-defined]
     else:
@@ -41,7 +41,7 @@ def model_dump_json(obj: BaseModel) -> str:
 
 
 class TypeAdapter(Generic[T]):
-    def __init__(self, type_: Type[T]) -> None:
+    def __init__(self, type_: type[T]) -> None:
         self.type_ = type_
 
         if PYDANTIC_V2:
diff --git a/tests/conftest.py b/tests/conftest.py
index 6de52c5d..4571ea42 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -1,7 +1,7 @@
 import sys
+from collections.abc import Generator
 from dataclasses import dataclass
 from pathlib import Path
-from typing import Generator
 from unittest.mock import patch
 
 import pytest
diff --git a/tests/test_cli_deploy.py b/tests/test_cli_deploy.py
index 77d4b59b..33976ed2 100644
--- a/tests/test_cli_deploy.py
+++ b/tests/test_cli_deploy.py
@@ -2,7 +2,7 @@
 import string
 from datetime import timedelta
 from pathlib import Path
-from typing import Dict, Optional
+from typing import Optional
 from unittest.mock import patch
 
 import httpx
@@ -25,7 +25,7 @@
 assets_path = Path(__file__).parent / "assets"
 
 
-def _get_random_team() -> Dict[str, str]:
+def _get_random_team() -> dict[str, str]:
     name = "".join(random.choices(string.ascii_lowercase, k=10))
     slug = "".join(random.choices(string.ascii_lowercase, k=10))
     id = "".join(random.choices(string.digits, k=10))
@@ -35,7 +35,7 @@ def _get_random_team() -> Dict[str, str]:
 
 def _get_random_app(
     *, slug: Optional[str] = None, team_id: Optional[str] = None
-) -> Dict[str, str]:
+) -> dict[str, str]:
     name = "".join(random.choices(string.ascii_lowercase, k=10))
     slug = slug or "".join(random.choices(string.ascii_lowercase, k=10))
     id = "".join(random.choices(string.digits, k=10))
@@ -48,7 +48,7 @@ def _get_random_deployment(
     *,
     app_id: Optional[str] = None,
     status: str = "waiting_upload",
-) -> Dict[str, str]:
+) -> dict[str, str]:
     id = "".join(random.choices(string.digits, k=10))
     slug = "".join(random.choices(string.ascii_lowercase, k=10))
     app_id = app_id or "".join(random.choices(string.digits, k=10))
@@ -91,11 +91,11 @@ def test_chooses_login_option_when_not_logged_in(
         },
     ).mock(return_value=Response(200, json={"access_token": "test_token_1234"}))
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar, patch(
-        "fastapi_cloud_cli.commands.login.typer.launch"
-    ) as mock_launch:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+        patch("fastapi_cloud_cli.commands.login.typer.launch") as mock_launch,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -136,9 +136,10 @@ def test_chooses_waitlist_option_when_not_logged_in(
         },
     ).mock(return_value=Response(200))
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -200,9 +201,10 @@ def test_shows_waitlist_form_when_not_logged_in_longer_flow(
         },
     ).mock(return_value=Response(200))
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -220,9 +222,10 @@ def test_shows_error_when_trying_to_get_teams(
 
     respx_mock.get("/teams/").mock(return_value=Response(500))
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -240,9 +243,10 @@ def test_handles_invalid_auth(
 
     respx_mock.get("/teams/").mock(return_value=Response(401))
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -268,9 +272,10 @@ def test_shows_teams(
         )
     )
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -294,9 +299,10 @@ def test_asks_for_app_name_after_team(
         )
     )
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -325,9 +331,10 @@ def test_creates_app_on_backend(
         return_value=Response(201, json=_get_random_app(team_id=team["id"]))
     )
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -353,9 +360,10 @@ def test_uses_existing_app(
         return_value=Response(200, json={"data": [app_data]})
     )
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -426,9 +434,10 @@ def test_exits_successfully_when_deployment_is_done(
         )
     )
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -668,9 +677,10 @@ def _deploy_without_waiting(respx_mock: respx.MockRouter, tmp_path: Path) -> Res
         return_value=Response(200)
     )
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         return runner.invoke(app, ["deploy", "--no-wait"])
@@ -723,9 +733,11 @@ def test_shows_error_for_invalid_waitlist_form_data(
         Keys.CTRL_C,  # Interrupt to avoid infinite loop
     ]
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar, patch("rich_toolkit.form.Form.run") as mock_form_run:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+        patch("rich_toolkit.form.Form.run") as mock_form_run,
+    ):
         mock_getchar.side_effect = steps
         # Simulate form returning data with invalid email field to trigger ValidationError
         mock_form_run.return_value = {
@@ -758,9 +770,10 @@ def test_shows_no_apps_found_message_when_team_has_no_apps(
         return_value=Response(200, json={"data": []})
     )
 
-    with changing_dir(tmp_path), patch(
-        "rich_toolkit.container.getchar"
-    ) as mock_getchar:
+    with (
+        changing_dir(tmp_path),
+        patch("rich_toolkit.container.getchar") as mock_getchar,
+    ):
         mock_getchar.side_effect = steps
 
         result = runner.invoke(app, ["deploy"])
@@ -806,9 +819,12 @@ def test_shows_error_message_on_build_exception(
         return_value=Response(200)
     )
 
-    with changing_dir(tmp_path), patch(
-        "fastapi_cloud_cli.utils.api.APIClient.stream_build_logs",
-        side_effect=error,
+    with (
+        changing_dir(tmp_path),
+        patch(
+            "fastapi_cloud_cli.utils.api.APIClient.stream_build_logs",
+            side_effect=error,
+        ),
     ):
         result = runner.invoke(app, ["deploy"])
 
@@ -1017,9 +1033,12 @@ def test_calls_upload_cancelled_when_user_interrupts(
         f"/deployments/{deployment_data['id']}/upload-cancelled"
     ).mock(return_value=Response(200))
 
-    with changing_dir(tmp_path), patch(
-        "fastapi_cloud_cli.commands.deploy._upload_deployment",
-        side_effect=KeyboardInterrupt(),
+    with (
+        changing_dir(tmp_path),
+        patch(
+            "fastapi_cloud_cli.commands.deploy._upload_deployment",
+            side_effect=KeyboardInterrupt(),
+        ),
     ):
         runner.invoke(app, ["deploy"])
 
@@ -1049,9 +1068,12 @@ def test_cancel_upload_swallows_exceptions(
         f"/deployments/{deployment_data['id']}/upload-cancelled"
     ).mock(return_value=Response(500))
 
-    with changing_dir(tmp_path), patch(
-        "fastapi_cloud_cli.commands.deploy._upload_deployment",
-        side_effect=KeyboardInterrupt(),
+    with (
+        changing_dir(tmp_path),
+        patch(
+            "fastapi_cloud_cli.commands.deploy._upload_deployment",
+            side_effect=KeyboardInterrupt(),
+        ),
     ):
         result = runner.invoke(app, ["deploy"])
 
diff --git a/tests/test_env_delete.py b/tests/test_env_delete.py
index c4d1f4d5..ea2d39a5 100644
--- a/tests/test_env_delete.py
+++ b/tests/test_env_delete.py
@@ -122,8 +122,9 @@ def test_shows_selector_for_environment_variables(
         return_value=Response(204)
     )
 
-    with changing_dir(configured_app), patch(
-        "rich_toolkit.container.getchar", side_effect=steps
+    with (
+        changing_dir(configured_app),
+        patch("rich_toolkit.container.getchar", side_effect=steps),
     ):
         result = runner.invoke(app, ["env", "delete"])
 
diff --git a/tests/test_env_set.py b/tests/test_env_set.py
index 8bdce4af..5cd7738e 100644
--- a/tests/test_env_set.py
+++ b/tests/test_env_set.py
@@ -80,8 +80,9 @@ def test_asks_for_name_and_value(
 
     respx_mock.post("/apps/123/environment-variables/").mock(return_value=Response(200))
 
-    with changing_dir(configured_app), patch(
-        "rich_toolkit.container.getchar", side_effect=steps
+    with (
+        changing_dir(configured_app),
+        patch("rich_toolkit.container.getchar", side_effect=steps),
     ):
         result = runner.invoke(app, ["env", "set"])
 
diff --git a/tests/utils.py b/tests/utils.py
index 562e9941..d2c597b1 100644
--- a/tests/utils.py
+++ b/tests/utils.py
@@ -1,9 +1,10 @@
 import base64
 import json
 import os
+from collections.abc import Generator
 from contextlib import contextmanager
 from pathlib import Path
-from typing import Any, Dict, Generator, Union
+from typing import Any, Union
 
 
 @contextmanager
@@ -16,7 +17,7 @@ def changing_dir(directory: Union[str, Path]) -> Generator[None, None, None]:
         os.chdir(initial_dir)
 
 
-def build_logs_response(*logs: Dict[str, Any]) -> str:
+def build_logs_response(*logs: dict[str, Any]) -> str:
     """Helper to create NDJSON build logs response."""
     return "\n".join(json.dumps(log) for log in logs)
 
@@ -29,7 +30,7 @@ class Keys:
     TAB = "\t"
 
 
-def create_jwt_token(payload: Dict[str, Any]) -> str:
+def create_jwt_token(payload: dict[str, Any]) -> str:
     # Note: This creates a JWT with an invalid signature, but that's OK for our tests
     # since we only parse the payload, not verify the signature.
 
diff --git a/uv.lock b/uv.lock
index e718c27f..2b309a43 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1,57 +1,29 @@
 version = 1
 revision = 3
-requires-python = ">=3.8"
+requires-python = ">=3.9"
 resolution-markers = [
     "python_full_version >= '3.10'",
-    "python_full_version == '3.9.*'",
-    "python_full_version >= '3.8.1' and python_full_version < '3.9'",
-    "python_full_version < '3.8.1'",
+    "python_full_version < '3.10'",
 ]
 
 [[package]]
 name = "annotated-types"
 version = "0.7.0"
 source = { registry = "https://pypi.org/simple" }
-dependencies = [
-    { name = "typing-extensions", version = "4.13.2", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version < '3.9'" },
-]
 sdist = { url = "https://files.pythonhosted.org/packages/ee/67/531ea369ba64dcff5ec9c3402f9f51bf748cec26dde048a2f973a4eea7f5/annotated_types-0.7.0.tar.gz", hash = "sha256:aff07c09a53a08bc8cfccb9c85b05f1aa9a2a6f23728d790723543408344ce89", size = 16081, upload-time = "2024-05-20T21:33:25.928Z" }
 wheels = [
     { url = "https://files.pythonhosted.org/packages/78/b6/6307fbef88d9b5ee7421e68d78a9f162e0da4900bc5f5793f6d3d0e34fb8/annotated_types-0.7.0-py3-none-any.whl", hash = "sha256:1f02e8b43a8fbbc3f3e0d4f0f4bfc8131bcb4eebe8849b8e5c773f3a1c582a53", size = 13643, upload-time = "2024-05-20T21:33:24.1Z" },
 ]
 
-[[package]]
-name = "anyio"
-version = "4.5.2"
-source = { registry = "https://pypi.org/simple" }
-resolution-markers = [
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