It has been tested with certifications for a record with MFA, application secret phrases for a record with MFA, qualifications without MFA, and 'Less secure application access' enabled (be careful about different devices). On ports 465 and 587, I've attempted everything above, but get the same error message on 'Test association'.
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I am a bit confused here, Confluence Cloud has its own SMTP server and does not have a way to be set to use an external one. So I am not sure what you are trying to do here.
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