Forgot the non-greedy on the first one.

.ttarpit.json

@@ -10,7 +10,7 @@
     }
   },
   "Triggers": [
-    "(?<File>.*):(?<Line>[0-9]+):(?<Col>[0-9]+):\\s*(?<ErrType>.*):\\s*(?<Message>.*)",
+    "(?<File>.*?):(?<Line>[0-9]+):(?<Col>[0-9]+):\\s*(?<ErrType>.*):\\s*(?<Message>.*)",
-    "(?<File>.*):(?<Line>[0-9]+):(?<Col>[0-9]+):\\s*(?<Message>.*)"
+    "(?<File>.*?):(?<Line>[0-9]+):(?<Col>[0-9]+):\\s*(?<Message>.*)"
   ]
 }