Network Map: I have 2 corp offices connected by 2 hardware VPN Firewalls. 3MB T1 North 1.5MB T1 South all static In the North I have a DC/GC on a server 2K3 R2 SP2 and Exchange 2003 SP2 on a mail server also 2K3 R2 SP2. 2 servers in the north. In the South I have only 1 server. Server 2003 R2 SP2 running as second DC/GC with Exchange 2003 SP2. ( I know I know this is not optimal, neither is my budget) This has not been any issue for the last 5 years. Server is plenty powerful enough. dual Zeon 3.0 2mb, 4gb ram, 2 logical raid5 on 3 drives each, 2gb nic... System is idle all day. The North is the start and first of everything as far as network topology goes. The south idea was to move 5-15 empoyees email, my docs, and a network printer to there location because we were having issues with, not in a remote temp situtation, but full on work was too slow. Moving these services to ther ephysicall office speed things up by 10x fold. Recently the southern server had a catstrophic harddrive and MB failure. I had backups for the server but not full blown images or system restore, just store, brick, and file backups. I bought a new server got it all loaded up. I followed all the removal, prep, and installtion steps. Through the process I DID NOT encounter anything that was wierd or errors that I couldnt go past I had a pretty smooth removal and reinstall as far as all the AD and Networking Roles. I did my testing of sending emails in all direction internal external and so on.... seemed ok for a few weeks, but then I started getting reports of delivery issues???? I had the issues described below. OK here is the issue: ( I seem to be having 2 different issues but at the same time they feel related) So I have had users report to me that stuff is arriving and being delivered until weeks later. example. email sent from an internal recipient to an internal recipient along with a different email sent to an external recipient. So Not only does the email not show in my barracuda spam filter, any of my queues on either server, nobody has received them or NDRs but....... I can find them in the Sent folder in the clients outlook. 8 -9 days later still no NDR.... 14 days later all mail is received so I went straight for the time stamps and info(in the email on the outlook not any server logs or queues). OK 5-1-2010 7am message was sent. Message received 5-14-2010 11am. I am stating the time stamp info was correct. How does that not NDR 2-5 days later?? I really dont understand how this doesnt break long before that?? For this example I can confirm that 10 out 10 make it. Just more than 10 days later with correct time stamping. Item 2. not mixed with item 1 but at some point in time I went from the above to emails being sent int-ext or int-int only not ext-int and we are not even getting NDRs. 4 days later an email sent from me to user 1 doesnt show up right. The next day I send him another one and he gets it 1in 1 sec. So I send 5 emails 5 days in a row which is 25 and he gets 18 and the rest never NDR. since that test I have sent him 6 test emails and he got all 6. But last night a manger sent that user an email to come early on a day and he never got it. I send another test he got it. WTF.... This has really got me tripped up. I am not an exchage guru and I am starting to question what I think I know. My problem is not even that they are or are not NDR. They are escrow and mortgage emails that are very very time sensitive. I am open to suggestions. I wish I could just call microsoft on the phone to fix for sure but no funds. I am really in a jam.

I forgot I also have the issue where mail seems to disappear but if I reboot the server most show up and get delivered. Like this description http://social.technet.microsoft.com/Forums/en-US/exchangesvrgeneral/thread/54647b92-cc95-4b30-84ca-1b77d7fcefe2

Hi I think the key to seeing what is going on with these messages will be message tracking. I understand you have checked the queues and some logs, but i do not see mentioned of message tracking results. With message tracking enabled and run, we should be able to tell exactly where in Exchange the message is at, what time, and where it's next hop was. (This is assuming that the time stamps you gave are the items in the sent folder and their arrival times) Ensure message tracking is enabled: 1. Open Exchange System Manager 2. Navigate to the ServerName container, then right-click and choose properties of the affected server 3. Is "Enable Message Tracking" checked? NOTE: If this is not checked, please check it. If Message Tracking was already enabled: 1. Open Exchange System Manager 2. Click to expand "Tools" 3. Highlight the "Message Tracking Center" container 4. Fill in the fields on the right that fit the criteria of a message you have experienced the problem with 5. When the message appears on the bottom, click on it once to initialize a pop up with details Based on the time stamps: 1. Did the message ever leave the server? 2. Was it in a particular stage/event for the period of time the delay was experienced? 3. If so, which event/stage did the message sit in? (Example, if it took 6 days to deliver, do you see a gap in here?) Once we get more details from here, we can try to narrow it down. We would either bring in some diagnostic logging (depending on the stage of the message processing) or potentially look into 3rd party products. Kevin Ca MSFT