diff --git a/enterprise/integrations/jira/jira_view.py b/enterprise/integrations/jira/jira_view.py
index 1cc1e71046..eeff968ec3 100644
--- a/enterprise/integrations/jira/jira_view.py
+++ b/enterprise/integrations/jira/jira_view.py
@@ -132,8 +132,10 @@ class JiraExistingConversationView(JiraViewInterface):
             conversation_store = await ConversationStoreImpl.get_instance(
                 config, user_id
             )
-            metadata = await conversation_store.get_metadata(self.conversation_id)
-            if not metadata:
+
+            try:
+                await conversation_store.get_metadata(self.conversation_id)
+            except FileNotFoundError:
                 raise StartingConvoException('Conversation no longer exists.')
 
             provider_tokens = await self.saas_user_auth.get_provider_tokens()
diff --git a/enterprise/integrations/jira_dc/jira_dc_view.py b/enterprise/integrations/jira_dc/jira_dc_view.py
index 907d83bcd4..c60cbfc982 100644
--- a/enterprise/integrations/jira_dc/jira_dc_view.py
+++ b/enterprise/integrations/jira_dc/jira_dc_view.py
@@ -135,8 +135,10 @@ class JiraDcExistingConversationView(JiraDcViewInterface):
             conversation_store = await ConversationStoreImpl.get_instance(
                 config, user_id
             )
-            metadata = await conversation_store.get_metadata(self.conversation_id)
-            if not metadata:
+
+            try:
+                await conversation_store.get_metadata(self.conversation_id)
+            except FileNotFoundError:
                 raise StartingConvoException('Conversation no longer exists.')
 
             provider_tokens = await self.saas_user_auth.get_provider_tokens()
diff --git a/enterprise/integrations/linear/linear_view.py b/enterprise/integrations/linear/linear_view.py
index c2c0292f53..a0cf69a5f8 100644
--- a/enterprise/integrations/linear/linear_view.py
+++ b/enterprise/integrations/linear/linear_view.py
@@ -132,8 +132,10 @@ class LinearExistingConversationView(LinearViewInterface):
             conversation_store = await ConversationStoreImpl.get_instance(
                 config, user_id
             )
-            metadata = await conversation_store.get_metadata(self.conversation_id)
-            if not metadata:
+
+            try:
+                await conversation_store.get_metadata(self.conversation_id)
+            except FileNotFoundError:
                 raise StartingConvoException('Conversation no longer exists.')
 
             provider_tokens = await self.saas_user_auth.get_provider_tokens()
diff --git a/enterprise/integrations/slack/slack_view.py b/enterprise/integrations/slack/slack_view.py
index 4c5bc00ced..fdaed07971 100644
--- a/enterprise/integrations/slack/slack_view.py
+++ b/enterprise/integrations/slack/slack_view.py
@@ -263,8 +263,10 @@ class SlackUpdateExistingConversationView(SlackNewConversationView):
         # Check if conversation has been deleted
         # Update logic when soft delete is implemented
         conversation_store = await ConversationStoreImpl.get_instance(config, user_id)
-        metadata = await conversation_store.get_metadata(self.conversation_id)
-        if not metadata:
+
+        try:
+            await conversation_store.get_metadata(self.conversation_id)
+        except FileNotFoundError:
             raise StartingConvoException('Conversation no longer exists.')
 
         provider_tokens = await saas_user_auth.get_provider_tokens()
diff --git a/enterprise/tests/unit/integrations/jira/test_jira_view.py b/enterprise/tests/unit/integrations/jira/test_jira_view.py
index 0fcdcd8afa..07b885f59d 100644
--- a/enterprise/tests/unit/integrations/jira/test_jira_view.py
+++ b/enterprise/tests/unit/integrations/jira/test_jira_view.py
@@ -137,7 +137,9 @@ class TestJiraExistingConversationView:
     ):
         """Test conversation update with no metadata"""
         mock_store = AsyncMock()
-        mock_store.get_metadata.return_value = None
+        mock_store.get_metadata.side_effect = FileNotFoundError(
+            'No such file or directory'
+        )
         mock_store_impl.return_value = mock_store
 
         with pytest.raises(
diff --git a/enterprise/tests/unit/integrations/jira_dc/test_jira_dc_view.py b/enterprise/tests/unit/integrations/jira_dc/test_jira_dc_view.py
index 3efb616a62..bd1f1f352e 100644
--- a/enterprise/tests/unit/integrations/jira_dc/test_jira_dc_view.py
+++ b/enterprise/tests/unit/integrations/jira_dc/test_jira_dc_view.py
@@ -137,7 +137,9 @@ class TestJiraDcExistingConversationView:
     ):
         """Test conversation update with no metadata"""
         mock_store = AsyncMock()
-        mock_store.get_metadata.return_value = None
+        mock_store.get_metadata.side_effect = FileNotFoundError(
+            'No such file or directory'
+        )
         mock_store_impl.return_value = mock_store
 
         with pytest.raises(
diff --git a/enterprise/tests/unit/integrations/linear/test_linear_view.py b/enterprise/tests/unit/integrations/linear/test_linear_view.py
index 67acf720f0..dc410a9a5c 100644
--- a/enterprise/tests/unit/integrations/linear/test_linear_view.py
+++ b/enterprise/tests/unit/integrations/linear/test_linear_view.py
@@ -137,7 +137,9 @@ class TestLinearExistingConversationView:
     ):
         """Test conversation update with no metadata"""
         mock_store = AsyncMock()
-        mock_store.get_metadata.return_value = None
+        mock_store.get_metadata.side_effect = FileNotFoundError(
+            'No such file or directory'
+        )
         mock_store_impl.return_value = mock_store
 
         with pytest.raises(
diff --git a/openhands/server/services/conversation_service.py b/openhands/server/services/conversation_service.py
index 407c351b2f..2b0f61ee55 100644
--- a/openhands/server/services/conversation_service.py
+++ b/openhands/server/services/conversation_service.py
@@ -38,7 +38,7 @@ async def initialize_conversation(
     selected_branch: str | None,
     conversation_trigger: ConversationTrigger = ConversationTrigger.GUI,
     git_provider: ProviderType | None = None,
-) -> ConversationMetadata | None:
+) -> ConversationMetadata:
     if conversation_id is None:
         conversation_id = uuid.uuid4().hex
 
@@ -66,13 +66,8 @@ async def initialize_conversation(
         await conversation_store.save_metadata(conversation_metadata)
         return conversation_metadata
 
-    try:
-        conversation_metadata = await conversation_store.get_metadata(conversation_id)
-        return conversation_metadata
-    except Exception:
-        pass
-
-    return None
+    conversation_metadata = await conversation_store.get_metadata(conversation_id)
+    return conversation_metadata
 
 
 async def start_conversation(
@@ -190,9 +185,6 @@ async def create_new_conversation(
         git_provider,
     )
 
-    if not conversation_metadata:
-        raise Exception('Failed to initialize conversation')
-
     return await start_conversation(
         user_id,
         git_provider_tokens,