So I went back to this and I think the problem is we are forced to create a RSA_private_encrypt function even if all we want to do is sign.

https://github.com/openssl/openssl/blob/master/crypto/rsa/rsa_pmeth.c#L184

That branch gets hit on doing a TLS connection but not on creating a certificate. Ideally, shouldn't RSA_PKCS1_PSS_PADDING (and the other padding mode) also be handled by the RSA_sign of the engine implementation? I mean it is inside a function called pkey_rsa_sign. Though the RSA_sign function signature doesn't seem to allow specifying the padding.

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