Inbound Mail TLS Issue for certain domains

Posted on 2014-12-10
Medium Priority
Last Modified: 2016-02-25
Dear Experts,
I have a client, we have recently moved to exchange 2013 with mail being proxied via a Sophos UTM. The system works well and the client recieves inexcess of 8000+ spam emails daily which the UTM catches.

One of the suppliers that emails in gets this message:

Delay Report
Your message:
Re: Test Outbound
addressed to: user@domain.com
has the following delivery status:
451 4.7.5 [internal] TLS negotiation failed
What should you do?
This message is an informational Delivery Status Notification and does not require any further action.
Delivery to the recipients indicated above has been delayed.  You do not need to resend this message.  The server will continue to attempt message delivery.

I do not see the attempted delivery on the UTM SMTP logs, where as all the other mail is there whether it is being delivered to the exchange server or being quarantined or blackholed. I have also excluded the domain.com from TLS checking on the UTM, still nothing.

It is my belief the issue is with the sending servers? Could someone please help.
Question by:bluewaveit
LVL 16

Accepted Solution

Rajitha Chimmani earned 2000 total points
ID: 40492443
Appears to be on the sending end. It appears they have a forced TLS configuration. Have them disable TLS and try sending an email

Author Comment

ID: 40493675
Thank you for your comment, I have completed yet testing and have passed it back to their IT support team.

Expert Comment

ID: 40509679
This is terrible advice.  I have Exchange 2013 SP1 with a Sophos UTM proxying the mails as well.  I had to upgrade to version 9.304-9 for the TLS Negotiation to take place between Exchange and GMail.  Good luck trying to get GMail to stop sending out mail requiring TLS.  It probably is a good thing.  I did not have to do anything else.  By default Sophos will adapt automatically to the type of negotiation the sending server requires.

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