Hi
I am facing similar unsuccessful authentication issue, I did setup complete my domain DNS settings, enable DKIM, add Dmarc, MX and etc on domain provider, also verified the domain settings populated on office365.
For the test I am using "https://www.gmass.co/smtp-test# " provide my credentials "******@ultimatecookingcourse.com", select TLS when available, smtp.office365.com, 587, but the getting this error.
Connected to smtp://smtp.office365.com:587/?starttls=when-available<< 220 MWHPR10CA0009.outlook.office365.com Microsoft ESMTP MAIL Service ready at Sat, 14 Nov 2020 00:41:07 퍍>> EHLO [172.31.10.74]<< 250-MWHPR10CA0009.outlook.office365.com Hello [35.161.55.56]<< 250-SIZE 157286400<< 250-PIPELINING<< 250-DSN<< 250-ENHANCEDSTATUSCODES<< 250-STARTTLS<< 250-8BITMIME<< 250-BINARYMIME<< 250-CHUNKING<< 250 SMTPUTF8>> STARTTLS<< 220 2.0.0 SMTP server ready>> EHLO [172.31.10.74]<< 250-MWHPR10CA0009.outlook.office365.com Hello [35.161.55.56]<< 250-SIZE 157286400<< 250-PIPELINING<< 250-DSN<< 250-ENHANCEDSTATUSCODES<< 250-AUTH LOGIN XOAUTH2<< 250-8BITMIME<< 250-BINARYMIME<< 250-CHUNKING<< 250 SMTPUTF8>> AUTH LOGIN<< 334 VXNlcm5hbWU6>> YmVuYXppcm5vb3JAdWx0aW1hdGVjb29raW5nY291cnNlLmNvbQ==<< 334 UGFzc3dvcmQ6>> dXJvb2oxMjNAPw==<< 535 5.7.3 Authentication unsuccessful [MWHPR10CA0009.namprd10.prod.outlook.com]ERROR: 535: 5.7.3 Authentication unsuccessful [MWHPR10CA0009.namprd10.prod.outlook.com]
I can able to login on office 365 into my account and can able to send emails from outlook, but it is falling with https://www.gmass.co/smtp-test#. I appreciate if the Microsoft support team can check my account and exchange settings and fix this issue,
appreciate if they can resolve this issue.