Its luck of the draw at CT DMV. The clerks will do nothing with a title if you have one, since it isn't required.
https://www.ct.gov/dmv/cwp/view.asp?a=804&q=527244
If you go by what the DMV wants you to do, you will need to take the truck to the inspection lane. According to the website, military vehicles need to go to there for the VIN check.
That is where they take the opportunity to bust your chops. They can hit your for safety violations, namely the high rear bumper or lack there of. They see you as commercial. Wrongly, mind you. Argue all you want, you won't win. They are WRONG, since you are not commercial and are not trying to use it for commerce. Waste of time arguing with them unless you want to lawyer up and waste a lot of time later on. Maybe you get through without an issue, maybe not. I know some inspection lanes are better than others. Do NOT go the Wethersfield hub.
Another approach? Take it to any emissions center and have them do the vin check. Take the paperwork you need to the dmv and mention nothing of former military vehicle. You will probably be pushed right through and can get your classic vehicle plate. Classic vehicle is anything over 20 years old, there is no antique or old or special truck plate for this. Any old civic, pathfinder or whatever can get it. There is no weight designation, it is just a tax break. You aren't commercial, right? There will be no GVWR on your reg. Nothing in the statue limits what you can do with it. Now for insuring and what you actually haul, that is different and entirely on you.
http://www.ct.gov/dot/LIB/dot/documents/dbikes/14-1.pdf
That says 25 years, but it was changed to 20.
Now, if the dmv clerk pushes back, take your stuff and try again later at the same or a different DMV. From my own experience, different clerk, different results.
Good luck.