This has happened to me twice, so I figured I'd ask and see if it's a problem, and if so how I can help fix it. It seems that if I file IFR between two airports on a non-direct routing, a controller midway between my origin and destination doesn't know about the routing. The first instance happened to me on a flight between my home base (KCGF, Cleveland OH) and 3CK (Lake in the Hills, Chicago IL). The plane I was flying had a GPS that was placarded as VFR-only, so I dutifully filed airways. Somewhere over Indiana I was asked if I was direct my destination. I responded that no, I was V228, OBK, 3CK. The controller accepted that response without further comment, but I'm assuming he should have seen that without having to ask. The second, more recently, was on a flight from KCGF to KUMP (Indianapolis, IN). There was a line of storms on the direct path that I could circumnavigate by going south, so I filed KCGF, SGH, KUMP which took me down toward Columbus and Dayton before turning west. The Columbus approach controller called me to say there was weather between me and my destination and advised that heading south to about Newark would get me around it. I looked at my ADS-B radar to make sure nothing had changed significantly, looked at the route he offered, and replied that I was already direct to the SGH VOR. His response was to confirm that I was indeed direct the Springfield VOR, then told me that should be sufficient and to advise of deviations. In the first case to Chicago the airway routing and the direct routing were close enough that it probably didn't make much difference in terms of separation over the route. But on the way to Indianapolis there was a pretty significant difference between the route I was flying and the route the controller thought I was flying. It seems to me that could easily cause problems down the line. I'd be interested to see what comments any of the controllers on the board have.