Configuring sendmail to work with Office365

[MSec]

Hi,



I'm trying to get sendmail (sendmail-8.14.4-8.el6.x86_64) to relay messages through Office365 and I have the problem described here.
https://access.redhat.com/site/solutions/224303

I can get it to relay messages through gmail with no issues so my basic sendmail configuration seems to be ok.

I've been unable to find a tool that will allow me to decrypt the TLS session between the Outlook.com server and sendmail so I can't tell what extra authentication the server is asking for.



Has anyone configured this successfully?

Any info would be super helpful,

Thank you,
MSec

[Kees Theunissen]

MSec wrote:
> Hi,
>
>
>
> I'm trying to get sendmail (sendmail-8.14.4-8.el6.x86_64) to relay messages through Office365 and I have the problem described here.
> https://access.redhat.com/site/solutions/224303
>
> I can get it to relay messages through gmail with no issues so my basic sendmail configuration seems to be ok.
>
> I've been unable to find a tool that will allow me to decrypt the TLS session between the Outlook.com server and sendmail so I can't tell what extra authentication the server is asking for.

Try Swaks - Swiss Army Knife for SMTP
http://www.jetmore.org/john/code/swaks/

> Has anyone configured this successfully?
>
> Any info would be super helpful,
>
> Thank you,
> MSec

Regards,

Kees.

--
Kees Theunissen.

[MSec]

Thank you Kees,
Swaks helped me discover that office365 required the LOGIN not the PLAIN auth method.
That was the only issue.. It works now.
Very much appreciated.
MSec

[MSec]

Actually, I spoke to soon.
Swaks works with no problem
However when I use mail/sendmail I can send mail only to other email addresses in my corporate domain. If I try sending to any other email address I get a return email that says..
"reason: 550 5.7.1 Client does not have permissions to send as this sender"
Thanks,
MSec

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