Emails are delayed, someone shed some light for me...

I have a Exchange Server that I manage.  There is nothing on the Exchange Server except Exchange with 2 users and a BES setup and Symantec Mail Security with the defaults.
Everything seems to work fine then out of the blue my main user, who is also the guy who pays me tells me that hes getting delayed messages.
He will forward the message to me and cleary it shows it was sent by the sender for example at 3:30PM and my guy will not receive it until 7:00PM.
The weird thing is he eventually does receive and the other folks receive it immediatly.
I personally dont know how to check the Exchange logs or even what I should be looking for.
This happens often and it seems a reboot usually fixes it but i feel my guys frustration because hes losing money when emails arent showing up to his Outlook Email and BB until 3-4 hours later.

Help.
orlandotommyAsked:
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UbuntopConnect With a Mentor Commented:
I did not suggest that it was outlook.  The transit log for the email can be obtained in outlook as described.  It is the first step in deciding where the delay is.  We should see something like this.

Received: from mail.gmail.com (221.221.154.264) by
relay.mail.com (124.125.32.21) with smtp; Wed, 6 Feb 2008 10:18:59 -0600
Received: from relay.mail.com (124.125.32.21)  by
york.mail.com (124.125.32.21) with smtp; Wed, 6 Feb 2008 10:28:59 -0600
Received: from york.mail.com (124.125.32.21)  by
yourserver.domain.com (124.125.32.21) with smtp; Wed, 6 Feb 2008 10:29:03 -0600

(This shows a delay of ten minutes at the senders relay)
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Ugo MenaCommented:
I am taking a guess here as there are many places you will need to look, but the first place I would check is your DNS settings, on the server, and also within symantec, esp. if either is doing some type of dns lookup.
Are the delayed emails all from the same domain? have attachments?
What sort of internet connection do you have?

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orlandotommyAuthor Commented:
i have the dns set to use itself as primary, and the external dns of the provider as the secondary.
its on a t1 connection.
from the command prompt i can look up things left and right with nslookup with no problems at all.
the issues are very random with diff domains, there are no attachments.
thanks,
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UbuntopCommented:
If you can gain access to one of his delayed emails from within Outlook, right click it and choose OPTIONS.   In the text window, you will find all of the connection details for the message.  Look at each of the "received from" time stamps to find where the actual delay is. You may have to adjust for time zones.   If you find that the delay is on your exchange box, then we can look deeper.

A delayed inbound email has nothing to do with the exchange server's DNS, unless you are requiring a reverse DNS lookup on each sending domain. Or sender ID.
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Ugo MenaCommented:
ok good. just want to get the most obv. things out of the way first...one more
Have you checked to make sure it is not the send/receive schedule from within his outlook?
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orlandotommyAuthor Commented:
its not his outlook because its coming into his blackberry delayed as well..
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