We help IT Professionals succeed at work.
Get Started

Email Issue - Emails not received when sender uses reply

414 Views
Last Modified: 2012-05-11
OK, I have this weird issue that all of the sudden popped up.  It seems to happen most often with international email, but it may not be 100%.

Anyway for certain senders (from OUTSIDE my organization) try to send emails into my organization, they end up in a retry queue for some time, then eventually go into failure.  An NDR is sent to the sender eventually. The NDR is giving a 5.1.1 error code (I had the sender send me the NDR to my gmail account)

I had the sender try to send the exact same email again, but after hitting reply, to delete the recipients address and then type it  in fully manually (no auto-fill).  BAM! The email went through.

I had an idea, since most (possibly all) the issues were coming from international senders.  I had a user who was having similar issues when sending to a company in another country, but only when using reply.  I found that for some reason, when using reply, outlook was using a 'custom' protocol to send the email.  I can't for the life of me find where I saw this, but somewhere under the outgoing message preferences there was a field for protocol, and in it was "CUSTOM" and"MAILTO".  Now I'm aware of what MAILTO is (html).  Once we had the user change this to smtp, or, type the address in manually, it went through.
Comment
Watch Question
Co-Owner
CERTIFIED EXPERT
Top Expert 2011
Commented:
This problem has been solved!
Unlock 1 Answer and 6 Comments.
See Answer
Why Experts Exchange?

Experts Exchange always has the answer, or at the least points me in the correct direction! It is like having another employee that is extremely experienced.

Jim Murphy
Programmer at Smart IT Solutions

When asked, what has been your best career decision?

Deciding to stick with EE.

Mohamed Asif
Technical Department Head

Being involved with EE helped me to grow personally and professionally.

Carl Webster
CTP, Sr Infrastructure Consultant
Ask ANY Question

Connect with Certified Experts to gain insight and support on specific technology challenges including:

  • Troubleshooting
  • Research
  • Professional Opinions
Did You Know?

We've partnered with two important charities to provide clean water and computer science education to those who need it most. READ MORE