2026-09-25 18:57:52 SERVER -> CLIENT: 220 PR1P264CA0105.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 25 Sep 2026 18:57:51 +0000 [08DF1A5C4434D0A2]
2026-09-25 18:57:52 CLIENT -> SERVER: EHLO test.orangeoakleaf.com
2026-09-25 18:57:52 SERVER -> CLIENT: 250-PR1P264CA0105.outlook.office365.com Hello [5.135.141.158]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-STARTTLS250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8
2026-09-25 18:57:52 CLIENT -> SERVER: STARTTLS
2026-09-25 18:57:52 SERVER -> CLIENT: 220 2.0.0 SMTP server ready
2026-09-25 18:57:52 CLIENT -> SERVER: EHLO test.orangeoakleaf.com
2026-09-25 18:57:52 SERVER -> CLIENT: 250-PR1P264CA0105.outlook.office365.com Hello [5.135.141.158]250-SIZE 157286400250-PIPELINING250-DSN250-ENHANCEDSTATUSCODES250-AUTH LOGIN XOAUTH2250-8BITMIME250-BINARYMIME250-CHUNKING250 SMTPUTF8
2026-09-25 18:57:52 CLIENT -> SERVER: AUTH LOGIN
2026-09-25 18:57:52 SERVER -> CLIENT: 334 VXNlcm5hbWU6
2026-09-25 18:57:52 CLIENT -> SERVER: [credentials hidden]
2026-09-25 18:57:52 SERVER -> CLIENT: 334 UGFzc3dvcmQ6
2026-09-25 18:57:52 CLIENT -> SERVER: [credentials hidden]
2026-09-25 18:57:57 SERVER -> CLIENT: 535 5.7.3 Authentication unsuccessful [PR1P264CA0105.FRAP264.PROD.OUTLOOK.COM 2026-09-25T18:57:57.320Z 08DF1A5C4434D0A2]
2026-09-25 18:57:57 SMTP ERROR: Password command failed: 535 5.7.3 Authentication unsuccessful [PR1P264CA0105.FRAP264.PROD.OUTLOOK.COM 2026-09-25T18:57:57.320Z 08DF1A5C4434D0A2]
SMTP Error: Could not authenticate.
2026-09-25 18:57:57 CLIENT -> SERVER: QUIT
2026-09-25 18:57:57 SERVER -> CLIENT: 221 2.0.0 Service closing transmission channel
SMTP Error: Could not authenticate.
❌ FAILED: SMTP Error: Could not authenticate.