diff --git a/src/askui/tools/askui/askui_ui_controller_grpc/desktop_agent_os_error.py b/src/askui/tools/askui/askui_ui_controller_grpc/desktop_agent_os_error.py
index 14a66aba..5b482aa0 100644
--- a/src/askui/tools/askui/askui_ui_controller_grpc/desktop_agent_os_error.py
+++ b/src/askui/tools/askui/askui_ui_controller_grpc/desktop_agent_os_error.py
@@ -1,5 +1,9 @@
-class DesktopAgentOsError(BaseException):
+class DesktopAgentOsError(Exception):
     """Base class for Desktop Agent OS errors.
 
     This error is raised when an error occurs in the Desktop Agent OS.
+
+    Inherits from `Exception` (not `BaseException`) so that the standard
+    `except Exception` handlers in the tool-calling loop can catch it and
+    surface it to the agent as a tool error result instead of crashing.
     """
diff --git a/tests/unit/models/shared/test_tool_error_handling.py b/tests/unit/models/shared/test_tool_error_handling.py
new file mode 100644
index 00000000..e02cd71b
--- /dev/null
+++ b/tests/unit/models/shared/test_tool_error_handling.py
@@ -0,0 +1,60 @@
+"""Tests that tool failures are surfaced to the agent instead of crashing.
+
+When a tool raises, the tool-calling loop is expected to catch the error and
+return a `ToolResultBlockParam` with `is_error=True` so the agent can react to
+it. This only works if the raised exception derives from `Exception`; a
+`BaseException` subclass would slip past the `except Exception` handler and
+crash the run instead. `DesktopAgentOsError` (raised e.g. when reading a remote
+file/directory that does not exist) must therefore behave like a regular
+`Exception`.
+"""
+
+from askui.models.shared.agent_message_param import (
+    ToolResultBlockParam,
+    ToolUseBlockParam,
+)
+from askui.models.shared.tools import Tool, ToolCollection
+from askui.tools.askui.askui_ui_controller_grpc.desktop_agent_os_error import (
+    DesktopAgentOsError,
+)
+
+
+class _RaisingTool(Tool):
+    """A tool whose `__call__` always raises a `DesktopAgentOsError`."""
+
+    def __init__(self) -> None:
+        super().__init__(
+            name="raising_tool",
+            description="Always raises a DesktopAgentOsError.",
+        )
+
+    def __call__(self) -> str:
+        raise DesktopAgentOsError(self._error_message)
+
+    _error_message = (
+        "directory_iterator::directory_iterator: The system cannot find the "
+        'path specified.: "FrontEnd\\Traces"'
+    )
+
+
+class TestDesktopAgentOsErrorHandling:
+    def test_desktop_agent_os_error_is_an_exception(self) -> None:
+        assert issubclass(DesktopAgentOsError, Exception)
+
+    def test_raising_tool_returns_error_result_instead_of_crashing(self) -> None:
+        tool = _RaisingTool()
+        collection = ToolCollection(tools=[tool])
+        tool_use = ToolUseBlockParam(
+            id="tool_use_1",
+            input={},
+            name=tool.name,
+        )
+
+        results = collection.run([tool_use])
+
+        assert len(results) == 1
+        result = results[0]
+        assert isinstance(result, ToolResultBlockParam)
+        assert result.is_error is True
+        assert result.tool_use_id == "tool_use_1"
+        assert "FrontEnd\\Traces" in str(result.content)