Can an attacker guess the key given enough codes for the same key? And if so, how many times is it safe to use the same key?


I don't think there is any official limitations when it comes from standardization bodies such as NIST. However, there do seem to be some papers such as New Generic Attacks Against Hash-based MACs.

They show that HMAC may have less security than previously thought after the birthday bound. Generally, if you have a hash output size of, say 256 bits for SHA-256 then you may have to start worrying after $2^{128}$ messages. This is of course not a limit that should worry you.

Even for SHA-1 you're probably going to be fine. However, you may want to stop using (MD5 for which the bound is a worrying $2^{64}$) and SHA-1 by now for other reasons than just the output size; there are too many attacks on those hash functions and attacks only get better.

Just use a modern hash function - SHA-2 or SHA-3 - as base for HMAC and you'll be alright. For SHA-3 you might want to take a look at KMAC as well, although support for that particular MAC is sparse.

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    $\begingroup$ TL;DR: a single CPU is not powerful enough to make enough HMAC that it becomes unsafe, for any common hash, even the broken MD5 or SHA-1 as far as we know. But use at least SHA-256. $\endgroup$ – fgrieu Mar 2 at 4:44

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