diff --git a/api/app.py b/api/app.py
index 460c06ce..3ee8e02b 100644
--- a/api/app.py
+++ b/api/app.py
@@ -79,11 +79,16 @@ async def lifespan(app: FastAPI):
 
             api_url = f"http://{settings.host}:{settings.port}/v1"
             allowed_dirs = [workspace] if settings.allowed_dir else []
+            plans_dir_abs = os.path.abspath(
+                os.path.join(settings.claude_workspace, "plans")
+            )
+            plans_directory = os.path.relpath(plans_dir_abs, workspace)
             cli_manager = CLISessionManager(
                 workspace_path=workspace,
                 api_url=api_url,
                 allowed_dirs=allowed_dirs,
                 max_sessions=settings.max_cli_sessions,
+                plans_directory=plans_directory,
             )
 
             # Initialize session store
diff --git a/cli/manager.py b/cli/manager.py
index 2d24a8c5..92b88c86 100644
--- a/cli/manager.py
+++ b/cli/manager.py
@@ -28,6 +28,7 @@ class CLISessionManager:
         api_url: str,
         allowed_dirs: Optional[List[str]] = None,
         max_sessions: int = 10,
+        plans_directory: Optional[str] = None,
     ):
         """
         Initialize the session manager.
@@ -37,10 +38,12 @@ class CLISessionManager:
             api_url: API URL for the proxy
             allowed_dirs: Directories the CLI is allowed to access
             max_sessions: Maximum concurrent sessions
+            plans_directory: Directory for Claude Code CLI plan files (passed via --settings)
         """
         self.workspace = workspace_path
         self.api_url = api_url
         self.allowed_dirs = allowed_dirs or []
+        self.plans_directory = plans_directory
         self.max_sessions = max_sessions
 
         self._sessions: Dict[str, CLISession] = {}
@@ -83,6 +86,7 @@ class CLISessionManager:
                 workspace_path=self.workspace,
                 api_url=self.api_url,
                 allowed_dirs=self.allowed_dirs,
+                plans_directory=self.plans_directory,
             )
             self._pending_sessions[temp_id] = new_session
             logger.info(f"Created new session: {temp_id}")
diff --git a/cli/session.py b/cli/session.py
index 334f2c7b..d8cc32e8 100644
--- a/cli/session.py
+++ b/cli/session.py
@@ -17,10 +17,12 @@ class CLISession:
         workspace_path: str,
         api_url: str,
         allowed_dirs: Optional[List[str]] = None,
+        plans_directory: Optional[str] = None,
     ):
         self.workspace = os.path.normpath(os.path.abspath(workspace_path))
         self.api_url = api_url
         self.allowed_dirs = [os.path.normpath(d) for d in (allowed_dirs or [])]
+        self.plans_directory = plans_directory
         self.process: Optional[asyncio.subprocess.Process] = None
         self.current_session_id: Optional[str] = None
         self._is_busy = False
@@ -94,6 +96,10 @@ class CLISession:
                 for d in self.allowed_dirs:
                     cmd.extend(["--add-dir", d])
 
+            if self.plans_directory is not None:
+                settings_json = json.dumps({"plansDirectory": self.plans_directory})
+                cmd.extend(["--settings", settings_json])
+
             try:
                 self.process = await asyncio.create_subprocess_exec(
                     *cmd,
diff --git a/tests/test_cli.py b/tests/test_cli.py
index 7456ef5d..151a3267 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -1,8 +1,11 @@
 """Tests for cli/ module."""
 
-import pytest
 import asyncio
+import json
 import os
+
+import pytest
+
 from unittest.mock import AsyncMock, MagicMock, patch
 from messaging.event_parser import parse_cli_event
 
@@ -476,6 +479,36 @@ class TestCLISession:
             assert os.path.normpath("/dir1") in cmd
             assert os.path.normpath("/dir2") in cmd
 
+    @pytest.mark.asyncio
+    async def test_start_task_plans_directory(self):
+        """Test start_task includes --settings plansDirectory when plans_directory set."""
+        from cli.session import CLISession
+
+        session = CLISession(
+            "/tmp",
+            "http://localhost:8082/v1",
+            plans_directory="./agent_workspace/plans",
+        )
+
+        mock_process = AsyncMock()
+        mock_process.stdout.read.side_effect = [b""]
+        mock_process.stderr.read.return_value = b""
+        mock_process.wait.return_value = 0
+
+        with patch(
+            "asyncio.create_subprocess_exec", new_callable=AsyncMock
+        ) as mock_exec:
+            mock_exec.return_value = mock_process
+            async for _ in session.start_task("test"):
+                pass
+
+            cmd = mock_exec.call_args[0]
+            assert "--settings" in cmd
+            settings_idx = cmd.index("--settings")
+            assert settings_idx + 1 < len(cmd)
+            settings = json.loads(cmd[settings_idx + 1])
+            assert settings["plansDirectory"] == "./agent_workspace/plans"
+
     @pytest.mark.asyncio
     async def test_start_task_json_error(self):
         """Test handling of non-JSON output from CLI."""