Ozzy are you using the BETA or non BETA of Ensign? I'm going to assume the beta because that is the only place you can get IB backfill from Ensign right now. From the folks in the B-Line chatroom using the BETA there are quite a few issues still with it. Mainly with regard to remaining connected to the TWS. It is BETA so sadly one must expect the unexpected.
So which programs do positively work with the API? OwnData maybe? Tried Metatrader RT IB version and am not fully content. I got some backfill for the current 5 days with leaks and more than that seems to be difficult. They're still working on it though.