diff --git a/core/cli/main.py b/core/cli/main.py
index 0ea3cb42..ca1359bf 100644
--- a/core/cli/main.py
+++ b/core/cli/main.py
@@ -82,37 +82,36 @@ async def run_project(sm: StateManager, ui: UIBase, args) -> bool:
         telemetry.set("end_result", "interrupt")
         await sm.rollback()
     except APIError as err:
-        log.warning(f"LLM API error occurred: {err.message}")
-        capture_exception(err)
-        await ui.send_message(
-            f"Stopping Pythagora due to an error while calling the LLM API: {err.message}",
-            source=pythagora_source,
-        )
+        log.warning(f"an LLM API error occurred: {err.message}")
+        await send_error(ui, "error while calling the LLM API", err)
         telemetry.set("end_result", "failure:api-error")
         await sm.rollback()
     except CustomAssertionError as err:
-        log.warning(f"Anthropic assertion error occurred: {str(err)}")
-        capture_exception(err)
-        await ui.send_message(
-            f"Stopping Pythagora due to an error inside Anthropic SDK. {str(err)}",
-            source=pythagora_source,
-        )
+        log.warning(f"an Anthropic assertion error occurred: {str(err)}")
+        await send_error(ui, "error inside Anthropic SDK", err)
         telemetry.set("end_result", "failure:assertion-error")
         await sm.rollback()
     except Exception as err:
         log.error(f"Uncaught exception: {err}", exc_info=True)
-        capture_exception(err)
+        await send_error(ui, "an error", err)
 
-        stack_trace = telemetry.record_crash(err)
+        telemetry.record_crash(err)
         await sm.rollback()
-        await ui.send_message(
-            f"Stopping Pythagora due to error:\n\n{stack_trace}",
-            source=pythagora_source,
-        )
 
     return success
 
 
+async def send_error(ui: UIBase, error_source: str, err: Exception):
+    await ui.send_fatal_error(
+        f"Stopping Pythagora due to {error_source}:\n\n{err}",
+        source=pythagora_source,
+        extra_info={
+            "fatal_error": True,
+        },
+    )
+    capture_exception(err)
+
+
 async def start_new_project(sm: StateManager, ui: UIBase, args: Namespace = None) -> bool:
     """
     Start a new project.
@@ -368,7 +367,7 @@ async def async_main(
         success = await run_pythagora_session(sm, ui, args)
     except Exception as err:
         log.error(f"Uncaught exception in main session: {err}", exc_info=True)
-        capture_exception(err)
+        await send_error(ui, "an error", err)
         raise
     finally:
         await cleanup(ui)
diff --git a/core/ui/base.py b/core/ui/base.py
index cdea2997..adcbaa2d 100644
--- a/core/ui/base.py
+++ b/core/ui/base.py
@@ -516,6 +516,15 @@ class UIBase:
         """
         raise NotImplementedError()
 
+    async def send_fatal_error(
+        self,
+        message: str,
+        extra_info: Optional[dict] = None,
+        source: Optional[UISource] = None,
+        project_state_id: Optional[str] = None,
+    ):
+        pass
+
     async def send_front_logs_headers(
         self,
         project_state_id: str,
diff --git a/core/ui/console.py b/core/ui/console.py
index 2d8c7804..5dc5a373 100644
--- a/core/ui/console.py
+++ b/core/ui/console.py
@@ -240,6 +240,15 @@ class PlainConsoleUI(UIBase):
     ):
         pass
 
+    async def send_fatal_error(
+        self,
+        message: str,
+        extra_info: Optional[dict] = None,
+        source: Optional[UISource] = None,
+        project_state_id: Optional[str] = None,
+    ):
+        pass
+
     async def send_front_logs_headers(
         self,
         project_state_id: str,
diff --git a/core/ui/ipc_client.py b/core/ui/ipc_client.py
index 0fb4a66b..962f4fb9 100644
--- a/core/ui/ipc_client.py
+++ b/core/ui/ipc_client.py
@@ -68,6 +68,7 @@ class MessageType(str, Enum):
     LOAD_FRONT_LOGS = "loadFrontLogs"
     FRONT_LOGS_HEADERS = "frontLogsHeaders"
     CLEAR_MAIN_LOGS = "clearMainLogs"
+    FATAL_ERROR = "fatalError"
 
 
 class Message(BaseModel):
@@ -621,6 +622,21 @@ class IPCClientUI(UIBase):
 
         await self._send(MessageType.BACK_LOGS, content={"items": items})
 
+    async def send_fatal_error(
+        self,
+        message: str,
+        extra_info: Optional[dict] = None,
+        source: Optional[UISource] = None,
+        project_state_id: Optional[str] = None,
+    ):
+        await self._send(
+            MessageType.FATAL_ERROR,
+            content=message,
+            category=source.type_name if source else None,
+            project_state_id=project_state_id,
+            extra_info=extra_info,
+        )
+
     async def send_front_logs_headers(
         self,
         project_state_id: str,
diff --git a/core/ui/virtual.py b/core/ui/virtual.py
index 33243d36..ca94b241 100644
--- a/core/ui/virtual.py
+++ b/core/ui/virtual.py
@@ -228,6 +228,15 @@ class VirtualUI(UIBase):
     ):
         pass
 
+    async def send_fatal_error(
+        self,
+        message: str,
+        extra_info: Optional[dict] = None,
+        source: Optional[UISource] = None,
+        project_state_id: Optional[str] = None,
+    ):
+        pass
+
     async def send_front_logs_headers(
         self,
         project_state_id: str,
diff --git a/tests/cli/test_cli.py b/tests/cli/test_cli.py
index 7d24b69a..a5096225 100644
--- a/tests/cli/test_cli.py
+++ b/tests/cli/test_cli.py
@@ -342,7 +342,7 @@ async def test_main_handles_crash(mock_Orchestrator, tmp_path):
     mock_response = MagicMock(text="test", cancelled=False)
     mock_response.button = "test_project_type"  # Set a string value for project_type
     ui.ask_question = AsyncMock(return_value=mock_response)
-    ui.send_message = AsyncMock()
+    ui.send_fatal_error = AsyncMock()
 
     mock_orca = mock_Orchestrator.return_value
     mock_orca.run = AsyncMock(side_effect=RuntimeError("test error"))
@@ -350,5 +350,5 @@ async def test_main_handles_crash(mock_Orchestrator, tmp_path):
     success = await async_main(ui, db, args)
 
     assert success is False
-    ui.send_message.assert_called_once()
-    assert "test error" in ui.send_message.call_args[0][0]
+    ui.send_fatal_error.assert_called_once()
+    assert "test error" in ui.send_fatal_error.call_args[0][0]