The ocsp-update option should be between brackets
/etc/haproxy/ssl/mangadex.dev.pem [ocsp-update on] mangadex.dev *.mangadex.dev

Oh that makes more sense indeed; should have guessed so since other crt-list bind params used those indeed...

- does the OCSP update mechanism update the files on-disk?

No we never write anything on disk.
[...]
- if not, what happens if upon restart/reload of HAProxy the .ocsp file is outdated? will HAProxy aggressively try to get an up-to-date response before starting its listeners or will I be risking ssl issues by enabling OCSP must-staple with it?

The OCSP update mechanism will not block anything, it runs alongside all the "regular" HAProxy tasks. If I remember correctly, you cannot load outdated OCSP responses so you should not face this particular problem. But if you have many certificates for which OCSP update was activated and no OCSP response was provided, fetching all the missing responses will indeed take some time and OCSP stapling will temporarily fail for the given server certificates.

Hmm, I understand why it was decided to go that route, and indeed that is probably not too too hard to do... Though I can't help wonder if an opt-in mechanism similar to the server state file would make sense for it?

Either way, it all worked flawlessly within these constraints after putting the brackets, so that's great. Thanks.

Tristan

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