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Exchange \ Outlook - Email Lag

I have a reoccurring problem that I'm trying to wrap my head around.  It seems somewhat random as well.  The main issue is that it seems as though at random times, my users receive their mail after a long delay.  Sometimes as much as a day.  The issue is with both emails originating from outside as well as internal emails.  

We've also noticed that our exchange connection will randomly drop out.  Not too sure if these are related or not.  It also seems that it's possible that when the connection drops exchange jumps over to offline mode.  Now I can't vouch for what the end user is doing, but it's possibler that:
1. The connection to exchange times out
2. Outlook goes to offline mode
3. End user does not know outlook is in offline mode
4. The connection comes back
5. The user stays in offline mode (potentially until the next restart of outlook)

The items above are just an idea I had as to what could be causing the problem.  Sadly, I've never seen it myself - I only get work of the issue when an end user gets a flood of emails they should have previously seen

Any Suggestions?
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Hi There,
Please provide Which Exchange System you have been using, Exchange 2003, 2007 or 2010.
if it is Exchange 2003 :
1. Check the Exchange Server Services, Store Mounted state, and Routing Group queue in ESM.
if it is Exchange 2007/2010 : Check Hub Server status.
please provide more information about this issue.
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We're running EX03 on Server 2003.  As services are running.  Also, when this happens, it doesn't happen to all users.  It seems like its random when and who it happens to
Hi Jameson,

If it is happend for some user means it may not probably Server Issue, End user who reported the problem are in LAN, or Different Branches connected through WAN ?
Did you find any network drop ?   if the user reporting the problem check the connectivity between end user machine to Exchange server and observe for some time. and post the status
check outlook settings to see if it checks for updates of newemail...send/receive.
are they using rpc/http or regular outlook exchange.?
Is it in cached mode?
The situation seems to happen to: Our local users on our LAN, Our Users on our WAN (we have a few buildings spread across 20+ miles, linked either by Radio or T1)

My thought is what I wrote in the original post - that the connection drops for a moment or two (for whatever reason - that's something I'm looking into as well), Outlook goes offline, then never returns online (even if a connection could be established).  This just a thought, as I mentioned I never get to see the issue first hand until the user is bombarded with back emails.

So I'm wondering if there is a way to keep outlook from going offline even if there is no connection to the exchange server.
Cached mode SHOULD be off (we've ran into some rouge PC's with it on, and it causes crazy problems).  Most users are using regular old vanilla exchange protocol, but external users are using HTTP over RPC.  
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Thanks, I'm going to have to check the users who have had issues to see if that could be the problem.  Also, planning on upping the server timeout.  Also, may need to troubleshoot my network a bit.