diff --git a/python/copilot/client.py b/python/copilot/client.py
index efb2b9d5..97496f1b 100644
--- a/python/copilot/client.py
+++ b/python/copilot/client.py
@@ -19,7 +19,7 @@
 import subprocess
 import threading
 from dataclasses import asdict, is_dataclass
-from typing import Any, Dict, List, Optional, cast
+from typing import Any, Optional, cast
 
 from .generated.session_events import session_event_from_dict
 from .jsonrpc import JsonRpcClient
@@ -28,9 +28,11 @@
 from .types import (
     ConnectionState,
     CopilotClientOptions,
+    CustomAgentConfig,
     GetAuthStatusResponse,
     GetStatusResponse,
     ModelInfo,
+    ProviderConfig,
     ResumeSessionConfig,
     SessionConfig,
     SessionMetadata,
@@ -132,7 +134,7 @@ def __init__(self, options: Optional[CopilotClientOptions] = None):
         self._process: Optional[subprocess.Popen] = None
         self._client: Optional[JsonRpcClient] = None
         self._state: ConnectionState = "disconnected"
-        self._sessions: Dict[str, CopilotSession] = {}
+        self._sessions: dict[str, CopilotSession] = {}
         self._sessions_lock = threading.Lock()
 
     def _parse_cli_url(self, url: str) -> tuple[str, int]:
@@ -218,7 +220,7 @@ async def start(self) -> None:
             self._state = "error"
             raise
 
-    async def stop(self) -> List[Dict[str, str]]:
+    async def stop(self) -> list[dict[str, str]]:
         """
         Stop the CLI server and close all active sessions.
 
@@ -237,7 +239,7 @@ async def stop(self) -> List[Dict[str, str]]:
             ...     for error in errors:
             ...         print(f"Cleanup error: {error['message']}")
         """
-        errors: List[Dict[str, str]] = []
+        errors: list[dict[str, str]] = []
 
         # Atomically take ownership of all sessions and clear the dict
         # so no other thread can access them
@@ -357,7 +359,7 @@ async def create_session(self, config: Optional[SessionConfig] = None) -> Copilo
                     definition["parameters"] = tool.parameters
                 tool_defs.append(definition)
 
-        payload: Dict[str, Any] = {}
+        payload: dict[str, Any] = {}
         if cfg.get("model"):
             payload["model"] = cfg["model"]
         if cfg.get("session_id"):
@@ -482,7 +484,7 @@ async def resume_session(
                     definition["parameters"] = tool.parameters
                 tool_defs.append(definition)
 
-        payload: Dict[str, Any] = {"sessionId": session_id}
+        payload: dict[str, Any] = {"sessionId": session_id}
         if tool_defs:
             payload["tools"] = tool_defs
 
@@ -612,7 +614,7 @@ async def get_auth_status(self) -> "GetAuthStatusResponse":
 
         return await self._client.request("auth.getStatus", {})
 
-    async def list_models(self) -> List["ModelInfo"]:
+    async def list_models(self) -> list["ModelInfo"]:
         """
         List available models with their metadata.
 
@@ -634,7 +636,7 @@ async def list_models(self) -> List["ModelInfo"]:
         response = await self._client.request("models.list", {})
         return response.get("models", [])
 
-    async def list_sessions(self) -> List["SessionMetadata"]:
+    async def list_sessions(self) -> list["SessionMetadata"]:
         """
         List all available sessions known to the server.
 
@@ -710,7 +712,9 @@ async def _verify_protocol_version(self) -> None:
                 f"Please update your SDK or server to ensure compatibility."
             )
 
-    def _convert_provider_to_wire_format(self, provider: Dict[str, Any]) -> Dict[str, Any]:
+    def _convert_provider_to_wire_format(
+        self, provider: ProviderConfig | dict[str, Any]
+    ) -> dict[str, Any]:
         """
         Convert provider config from snake_case to camelCase wire format.
 
@@ -720,7 +724,7 @@ def _convert_provider_to_wire_format(self, provider: Dict[str, Any]) -> Dict[str
         Returns:
             The provider configuration in camelCase wire format.
         """
-        wire_provider: Dict[str, Any] = {"type": provider.get("type")}
+        wire_provider: dict[str, Any] = {"type": provider.get("type")}
         if "base_url" in provider:
             wire_provider["baseUrl"] = provider["base_url"]
         if "api_key" in provider:
@@ -731,14 +735,16 @@ def _convert_provider_to_wire_format(self, provider: Dict[str, Any]) -> Dict[str
             wire_provider["bearerToken"] = provider["bearer_token"]
         if "azure" in provider:
             azure = provider["azure"]
-            wire_azure: Dict[str, Any] = {}
+            wire_azure: dict[str, Any] = {}
             if "api_version" in azure:
                 wire_azure["apiVersion"] = azure["api_version"]
             if wire_azure:
                 wire_provider["azure"] = wire_azure
         return wire_provider
 
-    def _convert_custom_agent_to_wire_format(self, agent: Dict[str, Any]) -> Dict[str, Any]:
+    def _convert_custom_agent_to_wire_format(
+        self, agent: CustomAgentConfig | dict[str, Any]
+    ) -> dict[str, Any]:
         """
         Convert custom agent config from snake_case to camelCase wire format.
 
@@ -748,7 +754,7 @@ def _convert_custom_agent_to_wire_format(self, agent: Dict[str, Any]) -> Dict[st
         Returns:
             The custom agent configuration in camelCase wire format.
         """
-        wire_agent: Dict[str, Any] = {"name": agent.get("name"), "prompt": agent.get("prompt")}
+        wire_agent: dict[str, Any] = {"name": agent.get("name"), "prompt": agent.get("prompt")}
         if "display_name" in agent:
             wire_agent["displayName"] = agent["display_name"]
         if "description" in agent:
diff --git a/python/copilot/jsonrpc.py b/python/copilot/jsonrpc.py
index 6be85c10..b9322fd4 100644
--- a/python/copilot/jsonrpc.py
+++ b/python/copilot/jsonrpc.py
@@ -10,7 +10,8 @@
 import json
 import threading
 import uuid
-from typing import Any, Awaitable, Callable, Dict, Optional, Union
+from collections.abc import Awaitable
+from typing import Any, Callable, Optional, Union
 
 
 class JsonRpcError(Exception):
@@ -41,9 +42,9 @@ def __init__(self, process):
             process: subprocess.Popen with stdin=PIPE, stdout=PIPE
         """
         self.process = process
-        self.pending_requests: Dict[str, asyncio.Future] = {}
+        self.pending_requests: dict[str, asyncio.Future] = {}
         self.notification_handler: Optional[Callable[[str, dict], None]] = None
-        self.request_handlers: Dict[str, RequestHandler] = {}
+        self.request_handlers: dict[str, RequestHandler] = {}
         self._running = False
         self._read_thread: Optional[threading.Thread] = None
         self._loop: Optional[asyncio.AbstractEventLoop] = None
diff --git a/python/copilot/session.py b/python/copilot/session.py
index 06409641..63a1cb0d 100644
--- a/python/copilot/session.py
+++ b/python/copilot/session.py
@@ -8,7 +8,7 @@
 import asyncio
 import inspect
 import threading
-from typing import Any, Callable, Dict, List, Optional, Set
+from typing import Any, Callable, Optional
 
 from .generated.session_events import SessionEvent, SessionEventType, session_event_from_dict
 from .types import (
@@ -62,9 +62,9 @@ def __init__(self, session_id: str, client: Any):
         """
         self.session_id = session_id
         self._client = client
-        self._event_handlers: Set[Callable[[SessionEvent], None]] = set()
+        self._event_handlers: set[Callable[[SessionEvent], None]] = set()
         self._event_handlers_lock = threading.Lock()
-        self._tool_handlers: Dict[str, ToolHandler] = {}
+        self._tool_handlers: dict[str, ToolHandler] = {}
         self._tool_handlers_lock = threading.Lock()
         self._permission_handler: Optional[PermissionHandler] = None
         self._permission_handler_lock = threading.Lock()
@@ -220,7 +220,7 @@ def _dispatch_event(self, event: SessionEvent) -> None:
             except Exception as e:
                 print(f"Error in session event handler: {e}")
 
-    def _register_tools(self, tools: Optional[List[Tool]]) -> None:
+    def _register_tools(self, tools: Optional[list[Tool]]) -> None:
         """
         Register custom tool handlers for this session.
 
@@ -307,7 +307,7 @@ async def _handle_permission_request(self, request: dict) -> dict:
             # Handler failed, deny permission
             return {"kind": "denied-no-approval-rule-and-could-not-request-from-user"}
 
-    async def get_messages(self) -> List[SessionEvent]:
+    async def get_messages(self) -> list[SessionEvent]:
         """
         Retrieve all events and messages from this session's history.
 
diff --git a/python/copilot/tools.py b/python/copilot/tools.py
index d69faa45..d9757820 100644
--- a/python/copilot/tools.py
+++ b/python/copilot/tools.py
@@ -9,7 +9,7 @@
 
 import inspect
 import json
-from typing import Any, Callable, Type, TypeVar, get_type_hints, overload
+from typing import Any, Callable, TypeVar, get_type_hints, overload
 
 from pydantic import BaseModel
 
@@ -33,7 +33,7 @@ def define_tool(
     *,
     description: str | None = None,
     handler: Callable[[T, ToolInvocation], R],
-    params_type: Type[T],
+    params_type: type[T],
 ) -> Tool: ...
 
 
@@ -42,7 +42,7 @@ def define_tool(
     *,
     description: str | None = None,
     handler: Callable[[Any, ToolInvocation], Any] | None = None,
-    params_type: Type[BaseModel] | None = None,
+    params_type: type[BaseModel] | None = None,
 ) -> Tool | Callable[[Callable[[Any, ToolInvocation], Any]], Tool]:
     """
     Define a tool with automatic JSON schema generation from Pydantic models.
diff --git a/python/copilot/types.py b/python/copilot/types.py
index ddf960f7..2a06be98 100644
--- a/python/copilot/types.py
+++ b/python/copilot/types.py
@@ -4,8 +4,9 @@
 
 from __future__ import annotations
 
+from collections.abc import Awaitable
 from dataclasses import dataclass
-from typing import Any, Awaitable, Callable, Dict, List, Literal, TypedDict, Union
+from typing import Any, Callable, Literal, TypedDict, Union
 
 from typing_extensions import NotRequired
 
@@ -47,7 +48,7 @@ class CopilotClientOptions(TypedDict, total=False):
     auto_start: bool  # Auto-start the CLI server on first use (default: True)
     # Auto-restart the CLI server if it crashes (default: True)
     auto_restart: bool
-    env: Dict[str, str]  # Environment variables for the CLI process
+    env: dict[str, str]  # Environment variables for the CLI process
 
 
 ToolResultType = Literal["success", "failure", "rejected", "denied"]
@@ -64,11 +65,11 @@ class ToolResult(TypedDict, total=False):
     """Result of a tool invocation."""
 
     textResultForLlm: str
-    binaryResultsForLlm: List[ToolBinaryResult]
+    binaryResultsForLlm: list[ToolBinaryResult]
     resultType: ToolResultType
     error: str
     sessionLog: str
-    toolTelemetry: Dict[str, Any]
+    toolTelemetry: dict[str, Any]
 
 
 class ToolInvocation(TypedDict):
@@ -86,7 +87,7 @@ class Tool:
     name: str
     description: str
     handler: ToolHandler
-    parameters: Dict[str, Any] | None = None
+    parameters: dict[str, Any] | None = None
 
 
 # System message configuration (discriminated union)
@@ -134,11 +135,11 @@ class PermissionRequestResult(TypedDict, total=False):
         "denied-no-approval-rule-and-could-not-request-from-user",
         "denied-interactively-by-user",
     ]
-    rules: List[Any]
+    rules: list[Any]
 
 
 PermissionHandler = Callable[
-    [PermissionRequest, Dict[str, str]],
+    [PermissionRequest, dict[str, str]],
     Union[PermissionRequestResult, Awaitable[PermissionRequestResult]],
 ]
 
@@ -151,23 +152,23 @@ class PermissionRequestResult(TypedDict, total=False):
 class MCPLocalServerConfig(TypedDict, total=False):
     """Configuration for a local/stdio MCP server."""
 
-    tools: List[str]  # List of tools to include. [] means none. "*" means all.
+    tools: list[str]  # List of tools to include. [] means none. "*" means all.
     type: NotRequired[Literal["local", "stdio"]]  # Server type
     timeout: NotRequired[int]  # Timeout in milliseconds
     command: str  # Command to run
-    args: List[str]  # Command arguments
-    env: NotRequired[Dict[str, str]]  # Environment variables
+    args: list[str]  # Command arguments
+    env: NotRequired[dict[str, str]]  # Environment variables
     cwd: NotRequired[str]  # Working directory
 
 
 class MCPRemoteServerConfig(TypedDict, total=False):
     """Configuration for a remote MCP server (HTTP or SSE)."""
 
-    tools: List[str]  # List of tools to include. [] means none. "*" means all.
+    tools: list[str]  # List of tools to include. [] means none. "*" means all.
     type: Literal["http", "sse"]  # Server type
     timeout: NotRequired[int]  # Timeout in milliseconds
     url: str  # URL of the remote server
-    headers: NotRequired[Dict[str, str]]  # HTTP headers
+    headers: NotRequired[dict[str, str]]  # HTTP headers
 
 
 MCPServerConfig = Union[MCPLocalServerConfig, MCPRemoteServerConfig]
@@ -185,10 +186,10 @@ class CustomAgentConfig(TypedDict, total=False):
     display_name: NotRequired[str]  # Display name for UI purposes
     description: NotRequired[str]  # Description of what the agent does
     # List of tool names the agent can use
-    tools: NotRequired[List[str] | None]
+    tools: NotRequired[list[str] | None]
     prompt: str  # The prompt content for the agent
     # MCP servers specific to agent
-    mcp_servers: NotRequired[Dict[str, MCPServerConfig]]
+    mcp_servers: NotRequired[dict[str, MCPServerConfig]]
     infer: NotRequired[bool]  # Whether agent is available for model inference
 
 
@@ -198,7 +199,7 @@ class SessionConfig(TypedDict, total=False):
 
     session_id: str  # Optional custom session ID
     model: Literal["gpt-5", "claude-sonnet-4", "claude-sonnet-4.5", "claude-haiku-4.5"]
-    tools: List[Tool]
+    tools: list[Tool]
     system_message: SystemMessageConfig  # System message configuration
     # List of tool names to allow (takes precedence over excluded_tools)
     available_tools: list[str]
@@ -213,16 +214,16 @@ class SessionConfig(TypedDict, total=False):
     # with delta_content are sent as the response is generated
     streaming: bool
     # MCP server configurations for the session
-    mcp_servers: Dict[str, MCPServerConfig]
+    mcp_servers: dict[str, MCPServerConfig]
     # Custom agent configurations for the session
-    custom_agents: List[CustomAgentConfig]
+    custom_agents: list[CustomAgentConfig]
     # Override the default configuration directory location.
     # When specified, the session will use this directory for storing config and state.
     config_dir: str
     # Directories to load skills from
-    skill_directories: List[str]
+    skill_directories: list[str]
     # List of skill names to disable
-    disabled_skills: List[str]
+    disabled_skills: list[str]
 
 
 # Azure-specific provider options
@@ -251,19 +252,19 @@ class ProviderConfig(TypedDict, total=False):
 class ResumeSessionConfig(TypedDict, total=False):
     """Configuration for resuming a session"""
 
-    tools: List[Tool]
+    tools: list[Tool]
     provider: ProviderConfig
     on_permission_request: PermissionHandler
     # Enable streaming of assistant message chunks
     streaming: bool
     # MCP server configurations for the session
-    mcp_servers: Dict[str, MCPServerConfig]
+    mcp_servers: dict[str, MCPServerConfig]
     # Custom agent configurations for the session
-    custom_agents: List[CustomAgentConfig]
+    custom_agents: list[CustomAgentConfig]
     # Directories to load skills from
-    skill_directories: List[str]
+    skill_directories: list[str]
     # List of skill names to disable
-    disabled_skills: List[str]
+    disabled_skills: list[str]
 
 
 # Options for sending a message to a session
@@ -272,7 +273,7 @@ class MessageOptions(TypedDict):
 
     prompt: str  # The prompt/message to send
     # Optional file/directory attachments
-    attachments: NotRequired[List[Attachment]]
+    attachments: NotRequired[list[Attachment]]
     # Message processing mode
     mode: NotRequired[Literal["enqueue", "immediate"]]
 
@@ -306,7 +307,7 @@ class GetAuthStatusResponse(TypedDict):
 class ModelVisionLimits(TypedDict, total=False):
     """Vision-specific limits"""
 
-    supported_media_types: List[str]
+    supported_media_types: list[str]
     max_prompt_images: int
     max_prompt_image_size: int
 
@@ -358,7 +359,7 @@ class ModelInfo(TypedDict):
 class GetModelsResponse(TypedDict):
     """Response from models.list"""
 
-    models: List[ModelInfo]
+    models: list[ModelInfo]
 
 
 class SessionMetadata(TypedDict):
diff --git a/python/e2e/test_session.py b/python/e2e/test_session.py
index cc6b6300..92ce9e0f 100644
--- a/python/e2e/test_session.py
+++ b/python/e2e/test_session.py
@@ -181,9 +181,16 @@ async def test_should_throw_error_resuming_nonexistent_session(self, ctx: E2ETes
             await ctx.client.resume_session("non-existent-session-id")
 
     async def test_should_list_sessions(self, ctx: E2ETestContext):
-        # Create a couple of sessions
+        import asyncio
+
+        # Create a couple of sessions and send messages to persist them
         session1 = await ctx.client.create_session()
+        await session1.send_and_wait({"prompt": "Say hello"})
         session2 = await ctx.client.create_session()
+        await session2.send_and_wait({"prompt": "Say goodbye"})
+
+        # Small delay to ensure session files are written to disk
+        await asyncio.sleep(0.2)
 
         # List sessions and verify they're included
         sessions = await ctx.client.list_sessions()
@@ -206,10 +213,16 @@ async def test_should_list_sessions(self, ctx: E2ETestContext):
             assert isinstance(session_data["isRemote"], bool)
 
     async def test_should_delete_session(self, ctx: E2ETestContext):
-        # Create a session
+        import asyncio
+
+        # Create a session and send a message to persist it
         session = await ctx.client.create_session()
+        await session.send_and_wait({"prompt": "Hello"})
         session_id = session.session_id
 
+        # Small delay to ensure session file is written to disk
+        await asyncio.sleep(0.2)
+
         # Verify session exists in the list
         sessions = await ctx.client.list_sessions()
         session_ids = [s["sessionId"] for s in sessions]
diff --git a/python/e2e/testharness/proxy.py b/python/e2e/testharness/proxy.py
index c1c857a7..e26ec65c 100644
--- a/python/e2e/testharness/proxy.py
+++ b/python/e2e/testharness/proxy.py
@@ -9,7 +9,7 @@
 import platform
 import re
 import subprocess
-from typing import Any, Dict, List, Optional
+from typing import Any, Optional
 
 import httpx
 
@@ -97,7 +97,7 @@ async def configure(self, file_path: str, work_dir: str):
             if resp.status_code != 200:
                 raise RuntimeError(f"Proxy config failed with status {resp.status_code}")
 
-    async def get_exchanges(self) -> List[Dict[str, Any]]:
+    async def get_exchanges(self) -> list[dict[str, Any]]:
         """Retrieve the captured HTTP exchanges from the proxy."""
         if not self._proxy_url:
             raise RuntimeError("Proxy not started")
diff --git a/python/uv.lock b/python/uv.lock
index 98bf0253..1c1dfb58 100644
--- a/python/uv.lock
+++ b/python/uv.lock
@@ -1,54 +1,28 @@
 version = 1
-revision = 2
-requires-python = ">=3.8"
+revision = 3
+requires-python = ">=3.9"
 resolution-markers = [
     "python_full_version >= '3.10'",
-    "python_full_version == '3.9.*'",
-    "python_full_version < '3.9'",
+    "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 = [
-    "python_full_version < '3.9'",
-]
-dependencies = [
-    { name = "exceptiongroup", marker = "python_full_version < '3.9'" },
-    { name = "idna", marker = "python_full_version < '3.9'" },
-    { name = "sniffio", marker = "python_full_version < '3.9'" },
-    { 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/4d/f9/9a7ce600ebe7804daf90d4d48b1c0510a4561ddce43a596be46676f82343/anyio-4.5.2.tar.gz", hash = "sha256:23009af4ed04ce05991845451e11ef02fc7c5ed29179ac9a420e5ad0ac7ddc5b", size = 171293, upload-time = "2024-10-13T22:18:03.307Z" }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/1b/b4/f7e396030e3b11394436358ca258a81d6010106582422f23443c16ca1873/anyio-4.5.2-py3-none-any.whl", hash = "sha256:c011ee36bc1e8ba40e5a81cb9df91925c218fe9b778554e0b56a21e1b5d4716f", size = 89766, upload-time = "2024-10-13T22:18:01.524Z" },
-]
-
 [[package]]
 name = "anyio"
 version = "4.12.0"
 source = { registry = "https://pypi.org/simple" }
-resolution-markers = [
-    "python_full_version >= '3.10'",
-    "python_full_version == '3.9.*'",
-]
 dependencies = [
-    { name = "exceptiongroup", marker = "python_full_version >= '3.9' and python_full_version < '3.11'" },
-    { name = "idna", marker = "python_full_version >= '3.9'" },
-    { name = "typing-extensions", version = "4.15.0", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version >= '3.9' and python_full_version < '3.13'" },
+    { name = "exceptiongroup", marker = "python_full_version < '3.11'" },
+    { name = "idna" },
+    { name = "typing-extensions", marker = "python_full_version < '3.13'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/16/ce/8a777047513153587e5434fd752e89334ac33e379aa3497db860eeb60377/anyio-4.12.0.tar.gz", hash = "sha256:73c693b567b0c55130c104d0b43a9baf3aa6a31fc6110116509f27bf75e21ec0", size = 228266, upload-time = "2025-11-28T23:37:38.911Z" }
 wheels = [
@@ -82,31 +56,38 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/d1/d6/3965ed04c63042e047cb6a3e6ed1a63a35087b6a609aa3a15ed8ac56c221/colorama-0.4.6-py2.py3-none-any.whl", hash = "sha256:4f1d9991f5acc0ca119f9d443620b77f9d6b33703e51011c16baf57afb285fc6", size = 25335, upload-time = "2022-10-25T02:36:20.889Z" },
 ]
 
+[[package]]
+name = "exceptiongroup"
+version = "1.3.1"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "typing-extensions", marker = "python_full_version < '3.13'" },
+]
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-    { name = "pluggy", version = "1.6.0", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version >= '3.10'" },
+    { name = "pluggy", marker = "python_full_version >= '3.10'" },
     { name = "pygments", marker = "python_full_version >= '3.10'" },
     { name = "tomli", marker = "python_full_version == '3.10.*'" },
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-resolution-markers = [
-    "python_full_version < '3.9'",
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-]
-sdist = { url = "https://files.pythonhosted.org/packages/52/6d/c6cf50ce320cf8611df7a1254d86233b3df7cc07f9b5f5cbcb82e08aa534/pytest_asyncio-0.24.0.tar.gz", hash = "sha256:d081d828e576d85f875399194281e92bf8a68d60d72d1a2faf2feddb6c46b276", size = 49855, upload-time = "2024-08-22T08:03:18.145Z" }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/96/31/6607dab48616902f76885dfcf62c08d929796fc3b2d2318faf9fd54dbed9/pytest_asyncio-0.24.0-py3-none-any.whl", hash = "sha256:a811296ed596b69bf0b6f3dc40f83bcaf341b155a269052d82efa2b25ac7037b", size = 18024, upload-time = "2024-08-22T08:03:15.536Z" },
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-
 [[package]]
 name = "pytest-asyncio"
 version = "1.2.0"
 source = { registry = "https://pypi.org/simple" }
 resolution-markers = [
-    "python_full_version == '3.9.*'",
+    "python_full_version < '3.10'",
 ]
 dependencies = [
-    { name = "backports-asyncio-runner", marker = "python_full_version == '3.9.*'" },
-    { name = "pytest", version = "8.4.2", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version == '3.9.*'" },
-    { name = "typing-extensions", version = "4.15.0", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version == '3.9.*'" },
+    { name = "backports-asyncio-runner", marker = "python_full_version < '3.10'" },
+    { name = "pytest", version = "8.4.2", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version < '3.10'" },
+    { name = "typing-extensions", marker = "python_full_version < '3.10'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/42/86/9e3c5f48f7b7b638b216e4b9e645f54d199d7abbbab7a64a13b4e12ba10f/pytest_asyncio-1.2.0.tar.gz", hash = "sha256:c609a64a2a8768462d0c99811ddb8bd2583c33fd33cf7f21af1c142e824ffb57", size = 50119, upload-time = "2025-09-12T07:33:53.816Z" }
 wheels = [
@@ -639,7 +416,7 @@ resolution-markers = [
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     { name = "backports-asyncio-runner", marker = "python_full_version == '3.10.*'" },
     { name = "pytest", version = "9.0.2", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version >= '3.10'" },
-    { name = "typing-extensions", version = "4.15.0", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version >= '3.10' and python_full_version < '3.13'" },
+    { name = "typing-extensions", marker = "python_full_version >= '3.10' and python_full_version < '3.13'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/90/2c/8af215c0f776415f3590cac4f9086ccefd6fd463befeae41cd4d3f193e5a/pytest_asyncio-1.3.0.tar.gz", hash = "sha256:d7f52f36d231b80ee124cd216ffb19369aa168fc10095013c6b014a34d3ee9e5", size = 50087, upload-time = "2025-11-10T16:07:47.256Z" }
 wheels = [
@@ -693,15 +470,6 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/b7/ce/149a00dd41f10bc29e5921b496af8b574d8413afcd5e30dfa0ed46c2cc5e/six-1.17.0-py2.py3-none-any.whl", hash = "sha256:4721f391ed90541fddacab5acf947aa0d3dc7d27b2e1e8eda2be8970586c3274", size = 11050, upload-time = "2024-12-04T17:35:26.475Z" },
 ]
 
-[[package]]
-name = "sniffio"
-version = "1.3.1"
-source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/a2/87/a6771e1546d97e7e041b6ae58d80074f81b7d5121207425c964ddf5cfdbd/sniffio-1.3.1.tar.gz", hash = "sha256:f4324edc670a0f49750a81b895f35c3adb843cca46f0530f79fc1babb23789dc", size = 20372, upload-time = "2024-02-25T23:20:04.057Z" }
-wheels = [
-    { url = "https://files.pythonhosted.org/packages/e9/44/75a9c9421471a6c4805dbf2356f7c181a29c1879239abab1ea2cc8f38b40/sniffio-1.3.1-py3-none-any.whl", hash = "sha256:2f6da418d1f1e0fddd844478f41680e794e6051915791a034ff65e5f100525a2", size = 10235, upload-time = "2024-02-25T23:20:01.196Z" },
-]
-
 [[package]]
 name = "tomli"
 version = "2.3.0"
@@ -776,26 +544,10 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/5a/c4/97958503cf62bfb7908d2a77b03b91a20499a7ff405f5a098c4989589f34/ty-0.0.2-py3-none-win_arm64.whl", hash = "sha256:fbdef644ade0cd4420c4ec14b604b7894cefe77bfd8659686ac2f6aba9d1a306", size = 9572022, upload-time = "2025-12-16T20:13:39.189Z" },
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-version = "4.13.2"
-source = { registry = "https://pypi.org/simple" }
-resolution-markers = [
-    "python_full_version < '3.9'",
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-]
-
 [[package]]
 name = "typing-extensions"
 version = "4.15.0"
 source = { registry = "https://pypi.org/simple" }
-resolution-markers = [
-    "python_full_version >= '3.10'",
-    "python_full_version == '3.9.*'",
-]
 sdist = { url = "https://files.pythonhosted.org/packages/72/94/1a15dd82efb362ac84269196e94cf00f187f7ed21c242792a923cdb1c61f/typing_extensions-4.15.0.tar.gz", hash = "sha256:0cea48d173cc12fa28ecabc3b837ea3cf6f38c6d1136f85cbaaf598984861466", size = 109391, upload-time = "2025-08-25T13:49:26.313Z" }
 wheels = [
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@@ -806,7 +558,7 @@ name = "typing-inspection"
 version = "0.4.2"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
-    { name = "typing-extensions", version = "4.15.0", source = { registry = "https://pypi.org/simple" }, marker = "python_full_version >= '3.9'" },
+    { name = "typing-extensions" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/55/e3/70399cb7dd41c10ac53367ae42139cf4b1ca5f36bb3dc6c9d33acdb43655/typing_inspection-0.4.2.tar.gz", hash = "sha256:ba561c48a67c5958007083d386c3295464928b01faa735ab8547c5692e87f464", size = 75949, upload-time = "2025-10-01T02:14:41.687Z" }
 wheels = [
diff --git a/test/snapshots/session/should_abort_a_session.yaml b/test/snapshots/session/should_abort_a_session.yaml
index 24b97b2d..4c7093ad 100644
--- a/test/snapshots/session/should_abort_a_session.yaml
+++ b/test/snapshots/session/should_abort_a_session.yaml
@@ -5,7 +5,7 @@ conversations:
       - role: system
         content: ${system}
       - role: user
-        content: run the shell command 'sleep 100' (note this works on both bash and PowerShell)
+        content: run the shell command 'sleep 100' (works on bash and PowerShell)
       - role: assistant
         tool_calls:
           - id: toolcall_0
@@ -19,12 +19,12 @@ conversations:
             type: function
             function:
               name: ${shell}
-              arguments: '{"description":"Run sleep 100 command","command":"sleep 100","mode":"sync","initial_wait":30}'
+              arguments: '{"command":"sleep 100","description":"Run sleep 100 command","mode":"sync","initial_wait":30}'
   - messages:
       - role: system
         content: ${system}
       - role: user
-        content: run the shell command 'sleep 100' (note this works on both bash and PowerShell)
+        content: run the shell command 'sleep 100' (works on bash and PowerShell)
       - role: assistant
         tool_calls:
           - id: toolcall_0
@@ -36,7 +36,7 @@ conversations:
             type: function
             function:
               name: ${shell}
-              arguments: '{"description":"Run sleep 100 command","command":"sleep 100","mode":"sync","initial_wait":30}'
+              arguments: '{"command":"sleep 100","description":"Run sleep 100 command","mode":"sync","initial_wait":30}'
       - role: tool
         tool_call_id: toolcall_0
         content: Intent logged
@@ -46,4 +46,4 @@ conversations:
       - role: user
         content: What is 2+2?
       - role: assistant
-        content: 2+2 = 4
+        content: 2 + 2 = 4
diff --git a/test/snapshots/session/should_delete_session.yaml b/test/snapshots/session/should_delete_session.yaml
new file mode 100644
index 00000000..fb8249d3
--- /dev/null
+++ b/test/snapshots/session/should_delete_session.yaml
@@ -0,0 +1,11 @@
+models:
+  - claude-sonnet-4.5
+conversations:
+  - messages:
+      - role: system
+        content: ${system}
+      - role: user
+        content: Hello
+      - role: assistant
+        content: Hello! I'm GitHub Copilot CLI, your terminal assistant. I can help you with software engineering tasks like
+          exploring code, making changes, running tests, debugging, and more. What would you like to work on?
diff --git a/test/snapshots/session/should_list_sessions.yaml b/test/snapshots/session/should_list_sessions.yaml
new file mode 100644
index 00000000..46835065
--- /dev/null
+++ b/test/snapshots/session/should_list_sessions.yaml
@@ -0,0 +1,18 @@
+models:
+  - claude-sonnet-4.5
+conversations:
+  - messages:
+      - role: system
+        content: ${system}
+      - role: user
+        content: Say hello
+      - role: assistant
+        content: Hello! I'm GitHub Copilot CLI, ready to help you with your software engineering tasks. What can I assist you
+          with today?
+  - messages:
+      - role: system
+        content: ${system}
+      - role: user
+        content: Say goodbye
+      - role: assistant
+        content: Goodbye! Feel free to return anytime you need help. 👋