office 365

[edwardgoodnow]

Same error no matter what options are used
SMTPError: connection encountered an error (0008A9C0BE7F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:355

This is on a CentOs 8 server with openssl 3 installed have tried every setting metnioned including specifying tls cipher with v3 and tls set to false and everything in between

[eleith]

i haven't personally tested connecting to an office365 smtp server, but i have connected to many other smtp servers using very similar settings (ex: port 587/starttls).

it is possible your error is either due to misconfiguration, or your centos was compiled with openssl in a way that it can't do a proper handshake with office365.