SMTP.office365.com Relay 535 5.7.3 authentication unsuccessful

Question

we have had a SMTP relay in place for over 2 years and now all of a sudden there are authentication errors from the setup.

the firewall is not blocking this was setup over 2 years ago.

the credentials are correct, as i have logged in to the portal with the same credentials as whats being used in the SMTP relay settings.

no settings have changed on the server side.

any insight as where i should start to look would be appreciated!

SMTP log:

2016-03-10 13:02:45 132.245.53.178 OutboundConnectionResponse SMTPSVC1 AD0 - 1886526628 - - 250-CY1PR0801CA0039.outlook.office365.com+Hello+[69.49.157.50] 0 0 62 0 140 SMTP - - - -

2016-03-10 13:02:45 132.245.53.178 OutboundConnectionCommand SMTPSVC1 AD0 - 1886526628 STARTTLS - - 0 0 8 0 140 SMTP - - - -

2016-03-10 13:02:45 132.245.53.178 OutboundConnectionResponse SMTPSVC1 AD0 - 1886526628 - - 220+2.0.0+SMTP+server+ready 0 0 27 0 203 SMTP - - - -

2016-03-10 13:02:45 132.245.53.178 OutboundConnectionCommand SMTPSVC1 AD0 - 1886526628 EHLO - webbersupply.com 0 0 4 0 374 SMTP - - - -

2016-03-10 13:02:45 132.245.53.178 OutboundConnectionResponse SMTPSVC1 AD0 - 1886526628 - - 250-CY1PR0801CA0039.outlook.office365.com+Hello+[69.49.157.50] 0 0 62 0 452 SMTP - - - -

2016-03-10 13:02:45 132.245.53.178 OutboundConnectionCommand SMTPSVC1 AD0 - 1886526628 AUTH - - 0 0 4 0 452 SMTP - - - -

2016-03-10 13:02:45 132.245.53.178 OutboundConnectionResponse SMTPSVC1 AD0 - 1886526628 - - 334+UGFzc3dvcmQ6 0 0 16 0 515 SMTP - - - -

2016-03-10 13:02:52 132.245.53.178 OutboundConnectionResponse SMTPSVC1 AD0 - 1886526628 - - 535+5.7.3+Authentication+unsuccessful 0 0 37 0 6224 SMTP - - - -

Answer 1

hi aaron,

to narrow down the issue, i’d like to collect some information:

1. which method of the smtp reply do you use, smtp relay or iis client submission?

2. when you mentioned “there are authentication errors from the setup”, can you upload a screenshot of the error message?

(1) click use rich formatting on the bottom of this thread->click insert image as the picture shows.

(2) on the pop-up window, click browse to select the screenshot. after it is uploaded, click insert.

3. based on the current situation, can you set up your office 365 accounts in outlook clients via smtp connection and send emails? here are the steps:

1) open outlook client -> file -> add account -> manual setup or additional server types -> pop or imap

2) on the following page, enter the following information: (account type is imap.)

3) please note: the *** Email address is removed for privacy *** is my office 365 email address.

4) in the email address field, please enter your office 365 email address.

5) in logion information region, enter your office 365 email address and password.

6) click more settings.

7) clicking ok according to the instructions.

best regards,

erick

Answer 2

Morning Eric,

thanks for the reply.

i just logged in and changed the password on the account and now i have mailflow from my smtp server.

unfortunately there was no notification from o365 as to the account was needing a password change.

Answer 3

Hi Aaron,

I’m glad the issue is fixed after changing passwords. Other community members experiencing the same issue can also benefit from this thread. If you have any questions when using Office 365 in the future, please feel free to post a new thread with details in our forum. We are always here to help you.

Best Regards,

Erick