I'd suggest the dropdown re-populate based on the server selected and be based on the cutoffs you use for the different configurations it generates. So, if you select Apache, it'd give you something like 1.x, 2.1.0 - 2.2.x, 2.3.x, etc based on which versions share configurations.

Well, for the GP the 'feature' might be to allow a 'latest' version string already?

Keeping track of each released version is probably a huge pain in the .. back. But 'latest' (which isn't selected for openssl for me, for example: It shows 0.9.8.h atm) might already help to get the most fitting configuration for the current set of software?

I assume you don't care about individual releases _unless_ they change the configuration syntax/offer different cipher options?

That's a valid point. I'd suggest capturing it in the issue https://github.com/mozilla/server-side-tls/issues/39

There's a number of edge cases but we can probably find a middle ground that works well enough for the general case.