diff --git a/capiscio_mcp/guard.py b/capiscio_mcp/guard.py
index 215cca6..eb54054 100644
--- a/capiscio_mcp/guard.py
+++ b/capiscio_mcp/guard.py
@@ -688,7 +688,18 @@ async def run_eval():
                 # We're in an async context, use run_coroutine_threadsafe
                 import concurrent.futures
                 future = asyncio.run_coroutine_threadsafe(run_eval(), loop)
-                result = future.result(timeout=30.0)
+                try:
+                    result = future.result(timeout=30.0)
+                except (TimeoutError, concurrent.futures.TimeoutError):
+                    future.cancel()
+                    raise GuardError(
+                        reason=DenyReason.INTERNAL_ERROR,
+                        detail=(
+                            "Guard evaluation timed out. This usually means the "
+                            "guard is being called outside of an MCP request context "
+                            "or the gRPC core server is not responding."
+                        ),
+                    )
             else:
                 # No event loop, create one
                 result = asyncio.run(run_eval())
diff --git a/pyproject.toml b/pyproject.toml
index 3ecccce..bb7b9ab 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -4,7 +4,7 @@ build-backend = "hatchling.build"
 
 [project]
 name = "capiscio-mcp"
-version = "2.7.1"
+version = "2.7.2"
 description = "Trust badges for MCP tool calls - RFC-006 & RFC-007 implementation"
 readme = "README.md"
 requires-python = ">=3.10"