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Email rejected by Exchange on SBS 2011

I have a user reporting that emails from a certain user are not making it to him. The server rejecting the email is a SBS 2011. I checked the email logs in Untangle spam filter (which sits before the exchange as a firewall and Spam filter) and the emails make it to the Untangle. Here is the log from Untangle
 email log from Untangle
The sending user is from rogers.com which is a yahoo email service

The reject email that the sending user got says this
Sorry, we were unable to deliver your message to the following address.

<user@featurefoods.ca>:
Message expired for domain featurefoods.ca
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Gerhardpet
Asked:
Gerhardpet
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1 Solution
 
Simon Butler (Sembee)ConsultantCommented:
That doesn't really mean a great deal. The message expired, so it simply sat somewhere in a queue.
How does the log timestamp connect to the email sent time? Close?
If so then there isn't much more you can do - you need to monitor the queues in Exchange to see if messages are building up. The queue viewer will give you more information while the message is delayed, rather than what you get after it has been rejected.

Simon.
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GerhardpetAuthor Commented:
When I go to the Message Tracking the email does not even show up. I see that there are emails from the same user in May, June and up to July the 14th. No problems up to that time and since then the user can email us anymore.

Do I have to literally watch the queue?

There got to be a simple reason why it does not work anymore considering that it worked up until the 14th.
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Simon Butler (Sembee)ConsultantCommented:
If the messages do not appear in message tracking then they are not getting through Exchange.
If a message is being held up by Exchange then you don't have to be there watching the queue constantly because in a default installation the message will queue for 48 hours.
However if the queue is clear then the problem has to be further up. That points the finger at your Untangle server.

Simon.
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GerhardpetAuthor Commented:
I'm at a complete lost with this. The user sent an email and Cc me. I got the email within seconds (i'm on Office365) and it never made it to the SBS 2011 Exchange. While the email was being sent I had the Untangle Spam filter turned off.

As I said before the email does not make it to the message tracking. The same users emails for May, June and up to July the 14th are in the message tracking.

Also just today another user emailed from the same provider (@rogers.com) and they also bounce back.

It must be exchange somehow. Untangle does not even request email if it were junk. It will just drop it if the score is 20 +

Can some help please? I'm desperate for a solution.
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Simon Butler (Sembee)ConsultantCommented:
You said you had Untangle turned off. What exactly does that mean? Is SBS answering the SMTP traffic from the internet? If not, and Untangle is still in the path, then that is still the most likely cause of the problems.

Simon.
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GerhardpetAuthor Commented:
I meant the Untangle Spam filter being turned off

Been doing a lot more troubleshooting. It is impossible that it is being held up by Untangle. All other emails flows fine and I see the @rogers.com emails in the Untangle Spam logs as spam score 0

Just did a test and as soon as the user sends an email from rogers.com to user@featurefoods.ca he get this bounce back

Sorry, we were unable to deliver your message to the following address

<user@featurefoods.ca>:
Message expired for domain featurefoods.ca

This is right after sending it. Again it shows up in the Untangle Spam log
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Simon Butler (Sembee)ConsultantCommented:
That isn't an Exchange error.
Therefore something else is generating the error.

If you have just turned off the spam filter of Untangle, then it is still involved in the message delivery. To prove it isn't the cause you need to bypass it completely. That is the only option.

That means when someone connects to your MX record host, it is SBS that answers, NOT the Untangle box.

Simon.
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GerhardpetAuthor Commented:
This seems to be a complete mystery.

I found this post that seems to be similar but no solution

http://www.experts-exchange.com/Networking/Protocols/Email/Q_23275425.html
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GerhardpetAuthor Commented:
Simon,
You are suggesting to check in the Queue viewer but from my understanding the queue only is for outgoing emails.

http://technet.microsoft.com/en-us/library/bb123934(v=exchg.150).aspx

Another forum post with users complaining with similar problems

http://forums.comcast.com/t5/E-Mail-and-Xfinity-Connect-Help/My-friend-sending-me-emails-some-I-get-some-go-back-to-them-as/td-p/603634

It seems to be related to yahoo or any IPS provider that uses Yahoo servers to send emails.
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Simon Butler (Sembee)ConsultantCommented:
Queue viewer will show both inbound and outbound emails.
If Exchange is unable to deliver a message to the store then it will queue. There is nothing in the article that you have linked to that indicates it is for outbound email only.
Dismount a database - you will quickly see emails start to queue.

Yahoo's email system is one of the most troublesome to deal with, AOL being the second most troublesome. It doesn't help that a lot of ISPs use it, although the UKs biggest ISP recently dropped it because of the problems it causes.

Simon.
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GerhardpetAuthor Commented:
I'm finally able to replicate this. It truly is like finding a needle in a haystack. I'm posting this for information purposes only. I know what the solution is (see below)

The user reported that he is using Outlook Express (on Window XP) and that is when the email does not make it to the inbox for the featurefoods.ca user.

So I have replicated the setup with Outlook Express (also on Windows XP). I get the same results.

When I send the email from Rogers/Yahoo's online service then the email makes it to the user at featurefoods.ca. When I send it from Outlook Express using the smtp configuration from Yahoo it does not make it to the inbox for the user at featurefoods.ca.

When I use Outlook Express using an smtp server from DNS Made Easy the email makes it to the user at featurefoods.ca.

Update: Also did the same test on Outlook 2010 with the same results. So we can also assume that this has something to so with the smtp server being used at Yahoo.

My solution: Windows XP and Outlook Express are no longer supported by Microsoft so the user will get unpredictable results. There is something about using Yahoo's outgoing smtp server with Outlook Express that makes the message fail.

Another observation is that in Untagle Spam filter logs both emails show up but it never makes it to the end users inbox when sent from Outlook Express.

I Hope this will help someone else with similar or same problems
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GerhardpetAuthor Commented:
Read my second last comment for the solution and findings
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