This is kind of a tricky question. You are right that terminal alpha hydroxy ketones will tautomerize to aldehydes which are reactive with the Tollens reagent, and non-terminal ones don’t exhibit that tautomerism. However, from personal experience, non-terminal alpha hydroxy ketones also tend to be fairly straightforward to oxidize (to diones) under mild conditions. I’ve never tried oxidizing them specifically with Tollens’ reagent, but I know copper(II) will do the trick, so I can imagine silver(I) might as well. Normally, this would be a 5 minute experiment: I’d just walk into lab, whip up a batch of Tollens’ reagent, and toss in some benzoin, but these aren’t normal times and I don’t know when I’ll be able to get back into lab.
So you’re right in the tautomerism part, but it’s possible that the oxidation could still proceed through a different mechanism even with non-terminal alpha hydroxy ketones.