smtp Mail disappearing in exchange

Soldato
Joined
30 Sep 2006
Posts
5,278
Location
Midlands, UK
Hi all,

we're desperate for help, and not even Microsoft themselves have come up with an answer for this.

Over the past 4 months we've experienced, 'seemingly' randomly an amount of sent emails that do not reach their destination and simply disappear in our exchange 2007 SP3 latest RU.
I supply details to our IT company of the exact time, date etc of the message, they search for it in the tracking filters, but cannot find it.
The mail is sitting in the users sent items, evidence at least that it has gone through the process of being 'sent' to our smtp server so to speak.
It may be that the user sends another email to the same recipient 10 mins later and it will be received. That's the randomness for ya. :rolleyes:

So, i asked our users to apply Delivery Receipts to every external email. If they receive a DR then surely that means its at least left our exchange server, and may possibly be caught up in the electric.net spam filters or further on that than.
If they don't receive a DR within 10 mins then i report it to our IT company, they search our exchange and as expected they cannot find the message.

Our IT company had to elevate this to Microsoft as they couldn't figure it out. MS had our IT company pipeline certain users and send their reports back to them.
So far, 3 weeks later nothing tangible has come of this.

As a company we are losing money and confidence (from clients) in our mailing system.
I can't find anyone else on the internet who is suffering from the same issues as us.

Our users either work off their local pc (win7 pro x64) or via RDS (ws2008 r2), and there is no obvious pattern as to who falls foul to this issue and why. We all use outlook 2010 (x86)

The only thing some users have said is that if they try to 'resend' or 'forward' an email that is sitting in their sent items and had otherwise got 'lost' and never reached its destination, it would still fail. However, creating a new message, and pasting the contents into it would often work fine.

MS know about this, but again, no real answers as to why it happens.

Our Exchange install is a hyper-v guest, so i'm wondering whether we should:
a) flatten it and rebuild
b) make a new vm with Exchange 2010 (or later) and migrate
c) go to hosted exchange for approx. 70 users

Your thoughts would be greatly appreciated as we're realy struggling with this.

Many thanks in advance
 
What are you running on site?
Server 2008 r2 domain
Exchange 2k7 SP3, RU 8v2.
is it SBS?
Nope, Standard R2
do you have more than one Exchange server?
Not anymore, we killed the old one off to eliminate it from the proceedings. Made no difference.

Have you configured an outbound smart host for your emails?
Yes we do have a smart host, to our electric.net spam filters. I think that has been turned on and off and i believe its made no difference to the problems we are having.

Thanks, keep em coming if you have any more questions or advice.
I'm in the midst of building a new vm, then we'll migrate over, unless we find a cure in the meantime.
 
Have you performed message tracking from your Exchange server, I read what you said above but perhaps your IT company are only tracking from the smart host onwards?

Have you enabled Protocol Logging on your Send Connector (Presumably for *). For Exchange 07 you enable it like this:

Set-SendConnector -Identity "Send Connector Name" -ProtocolLoggingLevel "Verbose"

That will put protocol logs into your Exchange directories, think it's under the Connectivity folder.

Have you double checked your Queues?

Get-TransportServer | Get-Queue

Check for messages stuck in Retry etc, or a buildup of messages.

Are the users with problems using cached mode or not? Do the messages appear in the Sent Items in OWA too?
 
Last edited:
Back
Top Bottom