Sending to greylisting servers sometimes fails, delayed message appears on Exchange reboot


we recently had to reboot our Exchange (Exchange 2003 running GFI mail Essentials) server and one of my users received a 4.7.1 Delayed message.

He also said that the recipient never received his message.

The message was:

Reporting-MTA: dns;

Final-Recipient: rfc822;
Action: delayed
Status: 4.7.1
Diagnostic-Code: smtp;450 4.7.1 <>: Recipient address rejected: Greylisted for 5 minutes
Will-Retry-Until: Wed, 14 Apr 2010 12:42:44 +0100
X-Display-Name: ''

We have the GlitchRetrySeconds set to 0x00000078 (120 seconds)

The recipient in question is using a smarthost.

I have attached a screenshot of our Message Tracking Center which shows the message as only being sent once.

Can anyone shed any light on this please?

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LetterpartAuthor Commented:
I have just spotted that there is a Hotfix available for this which I hadn't seen before. I will try this now.
LetterpartAuthor Commented:

just to confuse matters I sent an email to this user before applying the hotfix so I could see if the issue was resolved and it arrived after 3 resends.

Doesn't help with my testing!

Yeah,  I had this problem with Exchange and my solution is to use a smarthost.  I think using a smarthost is always a good move as it eliminates all these kind of issues.  The fact your recipient uses a smarthost is irrelevant here.  Smarthost's only apply to outgoing email and not incoming email.

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LetterpartAuthor Commented:
I'm going to continue testing as this still isn't resolved 100% but I haven't had a repeat of the issue.

We may look at a smarthost but to be honest Exchange is expensive enough and it should be man enough for the job.

LetterpartAuthor Commented:
I have given a C grade as it was not so much a solution but more a suggestion.

Hope you're not offended.
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