diff --git a/coderd/database/dump.sql b/coderd/database/dump.sql
index 9c2df36cab..ff743ba902 100644
--- a/coderd/database/dump.sql
+++ b/coderd/database/dump.sql
@@ -1216,6 +1216,17 @@ BEGIN
 END;
 $$;
 
+CREATE FUNCTION remove_mcp_server_config_id_from_chats() RETURNS trigger
+    LANGUAGE plpgsql
+    AS $$
+BEGIN
+	UPDATE chats
+	SET mcp_server_ids = array_remove(mcp_server_ids, OLD.id)
+	WHERE OLD.id = ANY(mcp_server_ids);
+	RETURN OLD;
+END;
+$$;
+
 CREATE FUNCTION remove_organization_member_role() RETURNS trigger
     LANGUAGE plpgsql
     AS $$
@@ -4435,6 +4446,10 @@ CREATE TRIGGER inhibit_enqueue_if_disabled BEFORE INSERT ON notification_message
 
 CREATE TRIGGER protect_deleting_organizations BEFORE UPDATE ON organizations FOR EACH ROW WHEN (((new.deleted = true) AND (old.deleted = false))) EXECUTE FUNCTION protect_deleting_organizations();
 
+CREATE TRIGGER remove_chat_mcp_server_config_id BEFORE DELETE ON mcp_server_configs FOR EACH ROW EXECUTE FUNCTION remove_mcp_server_config_id_from_chats();
+
+COMMENT ON TRIGGER remove_chat_mcp_server_config_id ON mcp_server_configs IS 'When an MCP server config is deleted, this trigger removes its ID from all chats.';
+
 CREATE TRIGGER remove_organization_member_custom_role BEFORE DELETE ON custom_roles FOR EACH ROW EXECUTE FUNCTION remove_organization_member_role();
 
 COMMENT ON TRIGGER remove_organization_member_custom_role ON custom_roles IS 'When a custom_role is deleted, this trigger removes the role from all organization members.';
diff --git a/coderd/database/migrations/000510_cleanup_chats_mcp_server_ids_on_delete.down.sql b/coderd/database/migrations/000510_cleanup_chats_mcp_server_ids_on_delete.down.sql
new file mode 100644
index 0000000000..15c10e19e6
--- /dev/null
+++ b/coderd/database/migrations/000510_cleanup_chats_mcp_server_ids_on_delete.down.sql
@@ -0,0 +1,2 @@
+DROP TRIGGER IF EXISTS remove_chat_mcp_server_config_id ON mcp_server_configs;
+DROP FUNCTION IF EXISTS remove_mcp_server_config_id_from_chats;
diff --git a/coderd/database/migrations/000510_cleanup_chats_mcp_server_ids_on_delete.up.sql b/coderd/database/migrations/000510_cleanup_chats_mcp_server_ids_on_delete.up.sql
new file mode 100644
index 0000000000..5366328b3c
--- /dev/null
+++ b/coderd/database/migrations/000510_cleanup_chats_mcp_server_ids_on_delete.up.sql
@@ -0,0 +1,41 @@
+-- Remove already-stale MCP server references before future deletes are
+-- handled by the trigger below.
+UPDATE chats
+SET mcp_server_ids = (
+	SELECT COALESCE(array_agg(ids.mcp_server_id ORDER BY ids.position), '{}'::uuid[])
+	FROM unnest(chats.mcp_server_ids) WITH ORDINALITY AS ids(mcp_server_id, position)
+	WHERE EXISTS (
+		SELECT 1
+		FROM mcp_server_configs
+		WHERE mcp_server_configs.id = ids.mcp_server_id
+	)
+)
+WHERE EXISTS (
+	SELECT 1
+	FROM unnest(chats.mcp_server_ids) AS ids(mcp_server_id)
+	WHERE NOT EXISTS (
+		SELECT 1
+		FROM mcp_server_configs
+		WHERE mcp_server_configs.id = ids.mcp_server_id
+	)
+);
+
+CREATE OR REPLACE FUNCTION remove_mcp_server_config_id_from_chats()
+	RETURNS TRIGGER AS
+$$
+BEGIN
+	UPDATE chats
+	SET mcp_server_ids = array_remove(mcp_server_ids, OLD.id)
+	WHERE OLD.id = ANY(mcp_server_ids);
+	RETURN OLD;
+END;
+$$ LANGUAGE plpgsql;
+
+CREATE TRIGGER remove_chat_mcp_server_config_id
+	BEFORE DELETE ON mcp_server_configs FOR EACH ROW
+	EXECUTE PROCEDURE remove_mcp_server_config_id_from_chats();
+
+COMMENT ON TRIGGER
+	remove_chat_mcp_server_config_id
+	ON mcp_server_configs IS
+		'When an MCP server config is deleted, this trigger removes its ID from all chats.';
diff --git a/coderd/mcp_test.go b/coderd/mcp_test.go
index add730960f..dde85f12e7 100644
--- a/coderd/mcp_test.go
+++ b/coderd/mcp_test.go
@@ -1396,10 +1396,11 @@ func TestChatWithMCPServerIDs(t *testing.T) {
 	// Create the chat model config required for creating a chat.
 	_ = createChatModelConfigForMCP(t, expClient)
 
-	// Create an enabled MCP server config.
-	mcpConfig := createMCPServerConfig(t, client, "chat-mcp-server", true)
+	// Create enabled MCP server configs.
+	mcpConfigA := createMCPServerConfig(t, client, "chat-mcp-server-a", true)
+	mcpConfigB := createMCPServerConfig(t, client, "chat-mcp-server-b", true)
 
-	// Create a chat referencing the MCP server.
+	// Create a chat referencing the MCP servers.
 	chat, err := expClient.CreateChat(ctx, codersdk.CreateChatRequest{
 		OrganizationID: firstUser.OrganizationID,
 		Content: []codersdk.ChatInputPart{
@@ -1408,16 +1409,24 @@ func TestChatWithMCPServerIDs(t *testing.T) {
 				Text: "hello with mcp server",
 			},
 		},
-		MCPServerIDs: []uuid.UUID{mcpConfig.ID},
+		MCPServerIDs: []uuid.UUID{mcpConfigA.ID, mcpConfigB.ID},
 	})
 	require.NoError(t, err)
 	require.NotEqual(t, uuid.Nil, chat.ID)
-	require.Contains(t, chat.MCPServerIDs, mcpConfig.ID)
+	require.ElementsMatch(t, []uuid.UUID{mcpConfigA.ID, mcpConfigB.ID}, chat.MCPServerIDs)
 
 	// Fetch the chat and verify the MCP server IDs persist.
 	fetched, err := expClient.GetChat(ctx, chat.ID)
 	require.NoError(t, err)
-	require.Contains(t, fetched.MCPServerIDs, mcpConfig.ID)
+	require.ElementsMatch(t, []uuid.UUID{mcpConfigA.ID, mcpConfigB.ID}, fetched.MCPServerIDs)
+
+	err = client.DeleteMCPServerConfig(ctx, mcpConfigA.ID)
+	require.NoError(t, err)
+
+	fetched, err = expClient.GetChat(ctx, chat.ID)
+	require.NoError(t, err)
+	require.NotContains(t, fetched.MCPServerIDs, mcpConfigA.ID)
+	require.Contains(t, fetched.MCPServerIDs, mcpConfigB.ID)
 }
 
 func createChatModelConfigForMCP(t testing.TB, client *codersdk.ExperimentalClient) codersdk.ChatModelConfig {