emailgtw error authenticating to Office365 smtp server

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Article ID: 7817

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Updated On:

Products

DX Infrastructure Management NIMSOFT PROBES

Issue/Introduction

Unable to configure the emailgtw probe settings using an Office365 SMTP server.

"Test" option in emailgtw probe SMTP menu fails and produces the following error in the emailgtw.log:

emailgtw: EHLO %MachineNameOfemailgdtwProbe%.domain.com
emailgtw: 250-%outlookserver.office365.com% Hello [1.1.1.2]
emailgtw: 250-SIZE 157286400
emailgtw: 250-PIPELINING
emailgtw: 250-DSN
emailgtw: 250-ENHANCEDSTATUSCODES
emailgtw: 250-AUTH LOGIN XOAUTH2
emailgtw: 250-8BITMIME
emailgtw: 250-BINARYMIME
emailgtw: 250 CHUNKING
emailgtw: (cmd_test_smtp_login) smtp_open succeeded
emailgtw: AUTH LOGIN
emailgtw: 334 VXNlcm5hbWU6
emailgtw: (mm_login) getting username and password for host 1.1.1.1]
emailgtw: mm_login - found match [1.1.1.1]
emailgtw: <suppressed>
emailgtw: 334 UGFzc3dvcmW6
emailgtw: <suppressed>
emailgtw: 535 5.7.3 Authentication unsuccessful [%outlookserver.testdomain.outlook.com]

Cause

This issue is associated with the authentication process to the Office365 managed by the Office365 Admin.

Environment

- emailgtw probe version 2.83
- Office365 SMTP server

Resolution

Here is are some helpful links to troubleshoot this problem:

 1. Use Telnet to verify SMTP communication outside of the emailgtw probe

How to Use Telnet to Test SMTP Communication
https://technet.microsoft.com/en-us/library/aa995718

 

 2. See the following link with a solution for the "535 5.7.3" SMTP error

https://answers.microsoft.com/en-us/msoffice/forum/msoffice_o365admin-mso_dep365/smtpoffice365com-relay-535-573-authentication/9de8d176-1c07-4e66-b14f-148d3bd51bbf.