Exchange 2003 Dropping Emails

For some reason, emails do not get delivered to the Outlook client's inbox.  We use Exchange 2003, and GFI for SPAM handling.

The basic scenario:
- User A sends email to user B (our company on Exchange 2003)
- Several days later User A contacts user B asking why there was no response to the original email.
- User B claims they never received the email.
- User A forwards the original email that was sent earlier to user B

{So, where did the email go?  I thought this might be an isolated situation, but then it happened several more times with the same user B. }

Now, check out this next scenario involving myself:
- User B send me an email via their iphone.
- I read it on my Droid (as I am out of the office).
- I go back to my office, open Outlook, and the email is not in my inbox.
- I check SPAM, and it is not there either.  It is as if it was never delivered to me.  

Is this an issue with ActiveSync?  
Could ActiveSync cause emails to get inadvertently deleted from the server upon reading them, or upon opening the email client on the Droid?
Or, is this somehow an interaction with the Iphone?  Since I received the initial email from the iPhone on my Droid, perhaps that is enough to rule out an issue with the IPhone.
For me to have received the email on the Driod, I would think it would have had to come to the Exchange Server first (as I am using the Corporate Email App).
One more thing, user B and myself are on the same domain.

Any ideas on this one?
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.

Alan HardistyCo-OwnerCommented:
It isn't going to be an Activesync problem but is most likely to be an issue with GFI.  Not used GFI's anti-spam software before so no specific advise relating to that, but I would try disabling it and getting User A to email User B and see if the email arrives.

Have you checked the queues on the server to make sure there is nothing waiting for local delivery?
jamunseyAuthor Commented:
I was ruling out GFI because I received the email on my Droid.  My assumption was that if it got to the Droid (which is setup with a corporate exchange account), then it would have gotten through GFI.

I am not sure how to check the queues on the Exchange Server, so if you have any insight on that, it would be great.  I wonder if there is a place where I could located if a message was deleted by the exchange system.
Alan HardistyCo-OwnerCommented:
Okay - can you check OWA to see if the email exists please.  It may be that Outlook is out of sync with the server.
Acronis True Image 2019 just released!

Create a reliable backup. Make sure you always have dependable copies of your data so you can restore your entire system or individual files.

jamunseyAuthor Commented:
Great suggestion.  Just checked OWA and it is not there.  This is all very strange.  It is almost as if the Exchange server thought it was given instructions to delete the email.
Alan HardistyCo-OwnerCommented:
Yep - that is what it sounds like.

Any AV software installed on the server?
Since both users are in your organization, I'd start with the message tracker, plugin the mail server and the senders AD account and track the message.  I should show a complete path from on users mailbox to the queue and then to the receiving mailbox.  If it's an exchange issue this should help narrow down the cause.
Also try checking the "bad mail" queue (\mailroot\vsi1\BadMail) for the message for messages that could not delivered for one reason or another.

Tony GiangrecoCommented:
I also use the exact same GFI setup with Exchange 2003 and 2008. I run Symantec Endpoint on both servers and once in a while have the same problem. I have tracked a few instances down to a fact that GFI has at least one server within their clusrter of servers that has a blacklisted IP and I also tracked the email being blocked from the sender's mail server due to that situation. You might want to keep that in mind.
jamunseyAuthor Commented:
- There is no AV on the actual Exchange Server.  
- I could not find the "BadMail" folder ... I went down the path provided from the Cdrive of the Server.  Perhaps I am starting in the wrong location.
- Also, not sure how to use message tracker or where it is located.  I can certainly do some research on that though.
- Regarding the GFI interaction:  I was ruling out GFI as the problem in this scenario because the email is being sent and received with the same domain.  So, I would not think a "blacklist" could affect it.  Now, perhaps the fact that the IPhone was used to send the initial email could change things somewhat ... but, I am not sure how.
Alan HardistyCo-OwnerCommented:
The fact that the messages are internal and then disappearing suggests that there might be some kind of policy in GFI in force that scans the store and then removes what it doesn't like.

Not knowing GFI - I can't give you specifics, but there is nothing natively in Exchange that would cause this sort of problem and the lack of AV on the server rules that out, so it is either being deleted by someone, or GFI is doing it.
jamunseyAuthor Commented:
The strange this is that the email came to my Droid, which leads me to believe it passed through GFI with no issues.  Could my "reading" of the email from the Driod device caused a delete on Exchange.  If so, I thought that exchange had a setting that kept "deleted" emails for a specified number of days for the purpose of recovery.  I am not sure "how" and "where" to check this, but I think this would be a worthwhile check.  If it is in the "deleted" list, then we know it did arrived and was "somehow" deleted before it got to my Outlook view.  But, at least we have confirmation that the email is on the exchange server.  Does anyone know how to check for the "deleted" emails on the exchange server?
The below articles would be helpful if you have set the retention time limit for the deleted items

Recover deleted items at the mailbox store level and in Public Folders.

Using OWA 2003 to Recover Deleted Items

Deleted Item Recovery and Deleted Mailbox Recovery
Alan HardistyCo-OwnerCommented:
How is your Droid configured?  SMTP / POP3 or Exchange?
jamunseyAuthor Commented:
Droid is configured using their Corporate Mail Utility (Exchange).
jamunseyAuthor Commented:
Closing this one out.  Never quite got to the bottom of the issue.  We have since moved off of Exchange, and have moved to the Cloud for our Email.

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
jamunseyAuthor Commented:
Comments in my last post.
jamunseyAuthor Commented:
Thanks for your help.
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

From novice to tech pro — start learning today.