17/03/2023, 10:16:44: SEND - sending mail message(s) - 1 message(s) in queue
17/03/2023, 10:16:44: SEND - Connecting to SMTP server smtp-mail.outlook.com on port 587
17/03/2023, 10:16:44: SEND - Initiating TLS handshake
>17/03/2023, 10:16:44: SEND - Certificate S/N: 0F12DC8955821D6D936BCF34E50F60C5, algorithm: RSA (2048 bits), issued from 7/26/2022 to 7/25/2023 11:59:59 PM, for 23 host(s): outlook.com, *.clo.footprintdns.com, *.hotmail.com, *.internal.outlook.com, *.live.com, *.nrb.footprintdns.com, *.office.com, *.office365.com, *.outlook.com, *.outlook.office365.com, attachment.outlook.live.net, attachment.outlook.office.net, attachment.outlook.officeppe.net, attachments.office.net, attachments-sdf.office.net, ccs.login.microsoftonline.com, ccs-sdf.login.microsoftonline.com, hotmail.com, mail.services.live.com, office365.com, outlook.office.com, substrate.office.com, substrate-sdf.office.com.
>17/03/2023, 10:16:44: SEND - Owner: "US", "Washington", "Redmond", "Microsoft Corporation", "outlook.com".
>17/03/2023, 10:16:44: SEND - Issuer: "US", "DigiCert Inc", "DigiCert Cloud Services CA-1". Valid from 9/25/2020 to 9/24/2030 11:59:59 PM.
>17/03/2023, 10:16:44: SEND - Root: "US", "DigiCert Inc", "www.digicert.com", "DigiCert Global Root CA". Valid from 11/10/2006 to 11/10/2031.
17/03/2023, 10:16:44: SEND - TLS handshake complete
17/03/2023, 10:16:44: SEND - connected to SMTP server
17/03/2023, 10:16:59: SEND - WARNING: there were no compatible authentication mechanisms detected
17/03/2023, 10:16:59: SEND - sending message to redacted@redacted.com
!17/03/2023, 10:17:04: SEND - Server reports error. The response is: 5.7.57 Client not authenticated to send mail. Error: 535 5.7.3 Authentication unsuccessful [LO4P265CA0247.GBRP265.PROD.OUTLOOK.COM 2023-03-17T10:17:06.291Z 08DB26BDCB0983EC]
!17/03/2023, 10:17:04: SEND - Connection to host broken (last commands sent were: "MAIL FROM:<redacted@hotmail.com> SIZE=331", "RSET")
17/03/2023, 10:17:04: SEND - connection finished - 0 message(s) sent
17/03/2023, 10:17:04: SEND - Some messages were not sent - check the log for details
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