I'm reopening this. Its probably not a regression but I was sure that we had progress for large files fixed in the past.

Yeah no progress for files larger then 32 bit o.O... But this used to work 😭

On 64 bit linux this works btw. so I think it comes down to the difference between 32 bit off_t and 64 bit off_t

Yeah, its the ugly off_t again. I am just testing how this works with single files above that threshold we worked quite a bit on this back in the days https://dev.gnupg.org/T2368

Yeah, probably a Windows/MinGW 32-bit problem. GpgME::Data does

off_t size = seek(0, SEEK_END);
seek(0, SEEK_SET);
std::string sizestr = std::to_string(size);
// Ignore errors as this is optional
gpgme_data_set_flag(d->data, "size-hint", sizestr.c_str());

Probably some issue with large files / integer overflow. I am testing on Windows with 32 bit.

Mh, let me check where the size hint should come from and why it might be missing in my windows test. That is indeed strange then.

For me this does work also when decrypting:

btw. this does not work on the decrypting side because kleopatra there apparently does not provide a size hint. So it goes:

Due to back porting another change the fix for 2.2 is now also needed in 2.4.

works with Gpg4win-4.1.1-beta295

I checked the upstream. For the reported issue, upstream version raises an error with REG_ERR_UNMATCHED_BRACKET.
That behavior is better (as we don't have particular reason to maintain different behavior from upstream version).
Also, I found another change from upstream for end of word check.

To replicate the problem it is best to use Windows. Should be solved with my commit. Note that the bug is specific to 2.4 dues to irts multi-card and app support. There was no problem on 2.2.

my Yubikey works, too, if I disable PIV. With enabled PIV:

Unfortunately I can't replicate that with my Yubikey on 2.4.1. Tried several variant and with and without keyboxd. My Yubikey has PIV disabled but I doubt that this is the problem.

Test with GnuPG 2.4.1-beta76 failed with "error getting current key info: invalid name":