POP Email Clients outbound emails to Exchange 2003 Server are disappearing

This is a private exchange server 2003. Most users are connected through Outlook 2010 Exchange protocol. A few users connect via pop setting the Exchange Server as the pop server and the smtp server. 2 days ago the outbound emails stopped flowing. The Outlook client says they are sent, but clients never receive them.
rhillsnapAsked:
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Wayne88Commented:
Do you see the emails in the Exchange queue?
Can you do a trace by using the Exchange message tracker?
Do you see the email in OWA?

If you see the email on the server and OWA but not on Outlook then the problem is with Outlook not displaying propery.  Take it off cached mode to see if the sent items get updated.
1
rhillsnapAuthor Commented:
The same scenario is occuring on all 4 users that are setup this way.
No, the email is not showing up in OWA Sent Items.
0
Wayne88Commented:
How about when you using the Message Tracking Center to track a message in Exchange Server?  Do you see any trace of the missing messages at all if they were passed to Exchange?
1
Ultimate Tool Kit for Technology Solution Provider

Broken down into practical pointers and step-by-step instructions, the IT Service Excellence Tool Kit delivers expert advice for technology solution providers. Get your free copy now.

rhillsnapAuthor Commented:
I looked through the log file and it does show traces of the messages in Exchange
0
rhillsnapAuthor Commented:
These 4 users are in England and we are in Dallas. That is why they pop in to retrieve email. But I set the same scenario up here locally and am getting the same results.
0
Wayne88Commented:
Ok, so Exchange did received the message it's just not in Outlook.  Have you tried taking Outlook off the cached mode (uncheck it).
1
rhillsnapAuthor Commented:
I do have 2 smtp virtual servers setup. One is on port 25 and the other on 465. The  4 in England are setup on 465 and I set mine up to port 25. Neither work.
0
rhillsnapAuthor Commented:
I dont think there is Cached Mode for POP setup
0
rhillsnapAuthor Commented:
I just sent another message and it shows up in the Exchange logs, but does not get delivered and it doesnt show up in OWA. If I send the same message from OWA it gets delivered instantly and works perfectly. It is just when you send from client using the POP Configuration on all 4 machines.
0
rhillsnapAuthor Commented:
I am getting event log 953 and System Manager says the Exchange Routing Engine is stopped. Dont know if these are  routine or part of my issue.
0
rhillsnapAuthor Commented:
Could an expired certificate cause this issue?
0
rhillsnapAuthor Commented:
It turns out my outbound spam filter was classifying those emails as unlicensed and quarantining them without any notification. Very frustrated with Proofpoint at the moment. It tooks hours researching this and 2 phone calls to them to finally resolve.
0

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
Wayne88Commented:
Hi rhillsnap, sorry for the late reply.  Glad you got it sorted out. Cheers!
0
rhillsnapAuthor Commented:
They made a couple of valid attempts to help, however I ended up solving it myself. It was a very tricky issue for anyone to resolve remotely.
0
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Exchange

From novice to tech pro — start learning today.

Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.