I'm going with Redwire's assessment here.
I hope you've been insulating the TO-3's with something like in the first picture. This is how I have all four of mine on the same heatsink mounted to an all aluminum case. A little non conductive thermal compound on both sides of the mica washer and you're good to go. I went the extra mile in that the holes that the transistors leads and mounting screws go through also are lined with nylon tubing so everything is insulated just to be on the safe side.
As long as everything is insulated properly you'll never have issues. If you can't insulate the transistors , you can insulate separate heatsinks with two 2N3055's each, just make sure the cases are at least tied together with a wire and don't just rely on the heatsink itself to act as a conductor, I wouldn't trust that. I made sure that when mine were all mounted, I used a continuity tester to make sure the cases were isolated, as a matter of fact, I checked everything before powering up, three times. Measure twice, cut once.