feat: add exponential backoff retry for transient SDK errors

src/claude/sdk_integration.py

@@ -146,6 +146,16 @@ def __init__(
         else:
             logger.info("No API key provided, using existing Claude CLI authentication")
 
+    def _is_retryable_error(self, exc: BaseException) -> bool:
+        """Return True for transient errors that warrant a retry.
+        asyncio.TimeoutError is intentional (user-configured timeout) — not retried.
+        Only non-MCP CLIConnectionError is considered transient.
+        """
+        if isinstance(exc, CLIConnectionError):
+            msg = str(exc).lower()
+            return "mcp" not in msg  # "server" alone is too broad
+        return False
+
     async def execute_command(
         self,
         prompt: str,
@@ -288,11 +298,49 @@ async def _run_client() -> None:
                 finally:
                     await client.disconnect()
 
-            # Execute with timeout
-            await asyncio.wait_for(
-                _run_client(),
-                timeout=self.config.claude_timeout_seconds,
-            )
+            # Execute with timeout, retrying on transient CLIConnectionError
+            max_attempts = max(1, self.config.claude_retry_max_attempts)
+
+            for attempt in range(max_attempts):
+                # Reset message accumulator each attempt so that a failed attempt
+                # does not pollute the next one with partial/duplicate messages.
+                # _run_client() closes over `messages` by reference (late-binding
+                # closure), so clearing it here is seen by every new call.
+                messages.clear()
+
+                if attempt > 0:
+                    delay = min(
+                        self.config.claude_retry_base_delay
+                        * (self.config.claude_retry_backoff_factor ** (attempt - 1)),
+                        self.config.claude_retry_max_delay,
+                    )
+                    logger.warning(
+                        "Retrying Claude SDK command",
+                        attempt=attempt + 1,
+                        max_attempts=max_attempts,
+                        delay_seconds=delay,
+                    )
+                    await asyncio.sleep(delay)
+                # Note: asyncio.TimeoutError raised by wait_for is intentionally
+                # NOT caught below — it propagates immediately to the outer
+                # `except asyncio.TimeoutError` handler, bypassing the retry
+                # loop entirely.  Timeouts reflect a user-configured hard limit
+                # and should not be retried.
+                try:
+                    await asyncio.wait_for(
+                        _run_client(),
+                        timeout=self.config.claude_timeout_seconds,
+                    )
+                    break  # success — exit retry loop
+                except CLIConnectionError as exc:
+                    if self._is_retryable_error(exc) and attempt < max_attempts - 1:
+                        logger.warning(
+                            "Transient connection error, will retry",
+                            attempt=attempt + 1,
+                            error=str(exc),
+                        )
+                        continue
+                    raise  # non-retryable or attempts exhausted
 
             # Extract cost, tools, and session_id from result message
             cost = 0.0

src/config/settings.py

@@ -26,6 +26,10 @@
     DEFAULT_RATE_LIMIT_BURST,
     DEFAULT_RATE_LIMIT_REQUESTS,
     DEFAULT_RATE_LIMIT_WINDOW,
+    DEFAULT_RETRY_BACKOFF_FACTOR,
+    DEFAULT_RETRY_BASE_DELAY,
+    DEFAULT_RETRY_MAX_ATTEMPTS,
+    DEFAULT_RETRY_MAX_DELAY,
     DEFAULT_SESSION_TIMEOUT_HOURS,
 )
 
@@ -121,6 +125,34 @@ class Settings(BaseSettings):
         description="List of explicitly disallowed Claude tools/commands",
     )
 
+    # Retry settings
+    claude_retry_max_attempts: int = Field(
+        DEFAULT_RETRY_MAX_ATTEMPTS,
+        ge=0,
+        description="Max retry attempts for transient SDK errors (0 = disabled)",
+    )
+    claude_retry_base_delay: float = Field(
+        DEFAULT_RETRY_BASE_DELAY,
+        ge=0,
+        description=(
+            "Base delay in seconds between retries. "
+            "0 means retries are attempted immediately with no pause."
+        ),
+    )
+    claude_retry_backoff_factor: float = Field(
+        DEFAULT_RETRY_BACKOFF_FACTOR,
+        gt=0,
+        description="Exponential backoff multiplier",
+    )
+    claude_retry_max_delay: float = Field(
+        DEFAULT_RETRY_MAX_DELAY,
+        ge=0,
+        description=(
+            "Maximum delay cap in seconds. "
+            "0 disables the cap entirely (delays grow unbounded with backoff)."
+        ),
+    )
+
     # Sandbox settings
     sandbox_enabled: bool = Field(
         True,

src/utils/constants.py

@@ -85,5 +85,11 @@
 DEFAULT_CLAUDE_BINARY = "claude"
 DEFAULT_CLAUDE_OUTPUT_FORMAT = "stream-json"
 
+# Retry defaults
+DEFAULT_RETRY_MAX_ATTEMPTS = 3
+DEFAULT_RETRY_BASE_DELAY = 1.0
+DEFAULT_RETRY_BACKOFF_FACTOR = 3.0
+DEFAULT_RETRY_MAX_DELAY = 30.0
+
 # Logging
 LOG_FORMAT = "%(asctime)s - %(name)s - %(levelname)s - %(message)s"

tests/unit/test_claude/test_sdk_integration.py

@@ -390,6 +390,90 @@ async def test_execute_command_no_resume_for_new_session(self, sdk_manager):
             not hasattr(captured_options[0], "resume") or not captured_options[0].resume
         )
 
+    async def test_retry_on_transient_cli_connection_error(self, sdk_manager):
+        """Test that transient CLIConnectionError triggers retry and succeeds."""
+        from claude_agent_sdk import CLIConnectionError
+
+        call_count = 0
+
+        async def flaky_receive():
+            nonlocal call_count
+            call_count += 1
+            if call_count == 1:
+                raise CLIConnectionError("connection reset")
+            # Second attempt succeeds - yield a ResultMessage
+            yield
+
+        # Use a config with 2 attempts
+        sdk_manager.config.claude_retry_max_attempts = 2
+
+        client = AsyncMock()
+        client.connect = AsyncMock()
+        client.disconnect = AsyncMock()
+        client.query = AsyncMock()
+        query_mock = AsyncMock()
+        query_mock.receive_messages = flaky_receive
+        client._query = query_mock
+
+        # Should not raise - second attempt succeeds
+        with patch("src.claude.sdk_integration.ClaudeSDKClient", return_value=client):
+            with patch("asyncio.sleep", new_callable=AsyncMock):
+                try:
+                    await sdk_manager.execute_command(
+                        prompt="Test",
+                        working_directory=Path("/test"),
+                    )
+                except Exception:
+                    pass  # Response parsing may fail - what matters is retry happened
+        assert call_count == 2
+
+    async def test_no_retry_on_mcp_connection_error(self, sdk_manager):
+        """Test that MCP CLIConnectionError is NOT retried."""
+        from claude_agent_sdk import CLIConnectionError
+
+        from src.claude.exceptions import ClaudeMCPError
+
+        client = AsyncMock()
+        client.connect = AsyncMock()
+        client.disconnect = AsyncMock()
+        client.query = AsyncMock(side_effect=CLIConnectionError("mcp server failed"))
+
+        with patch("src.claude.sdk_integration.ClaudeSDKClient", return_value=client):
+            with pytest.raises((ClaudeMCPError, Exception)):
+                await sdk_manager.execute_command(
+                    prompt="Test",
+                    working_directory=Path("/test"),
+                )
+        # Only called once - no retry for MCP errors
+        assert client.query.call_count == 1
+
+    async def test_retry_disabled_when_max_attempts_zero(self, sdk_manager):
+        """Test that setting max_attempts=0 effectively disables retries (1 attempt)."""
+        sdk_manager.config.claude_retry_max_attempts = 0
+        assert max(1, sdk_manager.config.claude_retry_max_attempts) == 1
+
+    def test_is_retryable_error_transient(self, sdk_manager):
+        """Test _is_retryable_error returns True for transient connection errors."""
+        from claude_agent_sdk import CLIConnectionError
+
+        assert (
+            sdk_manager._is_retryable_error(CLIConnectionError("connection reset"))
+            is True
+        )
+
+    def test_is_retryable_error_mcp(self, sdk_manager):
+        """Test _is_retryable_error returns False for MCP errors."""
+        from claude_agent_sdk import CLIConnectionError
+
+        assert (
+            sdk_manager._is_retryable_error(CLIConnectionError("mcp server failed"))
+            is False
+        )
+
+    def test_is_retryable_error_timeout(self, sdk_manager):
+        """Test _is_retryable_error returns False for timeout errors."""
+        assert sdk_manager._is_retryable_error(asyncio.TimeoutError()) is False
+
 
 class TestClaudeSandboxSettings:
     """Test sandbox and system_prompt settings on ClaudeAgentOptions."""