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Exchange 2003 and outlook Syncronization not working on cloned machine / server

itsmagic asked
Last Modified: 2010-03-06
Exchange 2003 running in virtual machine on VMWARE. Ten or twelve clients machines varioius OS's and outlooks 03 / 07.

The exchange database corrupted (grew to big for data disc in the virtual machine) So I eventually finished up having to restore an old Clone of the exchange machine (actually SBS 2003 with exchange) which runs in the datacenter.

The server fires up OK and to all intensive purposes is the same one that went down but 5 months older.

Clients can connect etc too and email downloads from a linux server into the exchange accounts via GFI Pop downloader with no problem. Can access via webmail and the certificate is the one originally installed as it is a cloned virtual machine.

Problem: the clients will not syncronise with the server to "upload" the missing email from the OST's to the Exchange mail box. Nor will it download email from the mailbox to the OST.

other email accounts come into the ost files too so basically the OST's are the most important element here. However some email has now come into the new exchange server.

If I Delete/Rename the OST files I will only be able to get a copy of the "old" mailboxes with some new email (A days worth now)

What is the best process to be able to restart syncronisation between the two? Exporting to a pst first then recreate an OST. on the client to start the syncronisation / sync with the server and then import the pst to the new OST ? or is there an easier less labour intesive way anyone knows of. (indeed will the importing of the pst work correctly as a potential solution?

Does anyone also know why a clone just 5 months "out of date" would not syncronise with the ost files when it was powered back on as a virtual machine? (I dont think the virtualisation has anything to do with the problem I just wanted to explain how exact a clone this is)

Any thoughts / advice / observations etc most appreciated!

Watch Question

If you move mail to a different folder in Outlook does it sync up to the server? E.G. Create a folder in Outlook and move an email from the inbox to the new folder and see if it sync's up to the server.


Hmmmm Interesting...  yes it does.

I also clicked on an email into outlook from another email account (non exchange pop) and it marks it as read in outlook and can be flagged. That is then echoed up on the exchange server mailbox. A sort of upload only sync?

Trying the reverse in webmail doesn't get reflected down to outlook.

Very curious now!


Further thought ... Although uploading to exchange the bulk of the email isn't - only the new stuff in outlook goes up.
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If you did have to go the route of exporting all OSTs to PST, you could use Exmerge ( http://www.microsoft.com/downloads/details.aspx?familyid=429163EC-DCDF-47DC-96DA-1C12D67327D5&displaylang=en ) on the server to import the PSTs to the mailbox.


The folders / email uploads to exchange no problem however changes on the server are not reflected down to outlook. Also new email into the server isn't brought down into outlook either so just getting the items up to the server isn't going to crack it.

I will do a test on a junior members outlook tommorrow with a new ost and see if that route works.

Trouble is that means a 160 mile round trip up to London (Might do some theatre and a hotel whilst up there as an excuse :-) ) Come to think of the Directors are working in Florida for a few months at the moment so maybe a trip out there to sort the client machines out :-) too! (Remote support when there's that much fun to be had? Nah....)

Obviously the best solution would be a server based one that did all the clients at the same time of course but I don't know if that will in fact be possible. It''s frustrating as it seems to partly do what it is supposed to but stops short in the one way sync it seems to be doing.

Will check out Exmerge soon too. Please keep the ideas coming though all good stuff! Thanks too for your efforts so far Olski.

All that really matters is that the emails are uploaded to exchange. Once this is done I'm faily confident a new Outlook profile with a new OST will download all the mail from the server. This may be something you want to test with your Junior member.

For remote support we use Dameware or VNC for client machines on a faster network connection to use <10Mb leased line, for remote workers on ADSL or a slower line we use GoToAssist - I don't think it's cheap but it is excellent. You don't need to install anything yourself you just send the users to a weblink that installs a plugin type thing and connects you to them. You can even reboot their machine and automatically be reconnected to them when it comes back up. Try the demo at: http://www.gotoassist.com/ (You'd think I was on a commision, but i'm not - I just love the simplicitty of it!)


Ah right with you now Olski - Two days without sleep means I am bit slow to get the big picture. I am sure you are right once the new ost is formed it should download the server side info correctly. Took some time for the penny to drop - my only defence is that its hard to nod off in the datacenter with all the freezing aircon on your left arm a hairdryer blast from the bank of servers the other side and noise to make a 747 take off sound quiet!

I really do think that is the solution but will keep you waiting until I test it before awarding the points ;-)  

Many thanks for the remote support tips I am in fact quite familiar with those as I support people all over the UK / Florida / Libya etc we use Propalms for a thin client solution too which helps keep things all in one spot to deal with anyway. Even Live Messenger with the remote support beats taking a long drive to London. I must confess to regular visits to Florida though as that is just too tempting.

Yeah I don't think remote support tools work very well to across the pond ;)

Did you get this to work in the end?


Hi Olski,

I managed to use some of the ideas you used above to narrow the problem down. There were further issues like a corrupt priv1.edb which eseutil fixed but syncronization problems remained for a variety of complex reasons. However, your ideas got me on the right diagnostic track and will undoubtedly help in future situation like this too. The moral support of knowing there are two heads on the case is worth its weight in gold too!

I have in fact decided to look for a completely new solution as the various fixes on exchange simply havent worked for whatever reason - one part fixed and another broke as a result etc. So I have put everyone on Linux for now with pop downloads from there instead whilst I have a rethink about servers generally.

Couple of things I have learnt in the process too - Keep mailboxes as small as possible we had half a dozen of about 1.5gb and  one of 3+ gb which takes ages to re download when recreating a new ost (http / RPC) In a Lan situation it may be more feasible but bandwidth charges and performance are killers when doing it over the web.

Secondly extra spare disc space is invaluable when trying to run eseutil etc. and finally backups other than server clones would still be a good idea. The clones did work but for some reason it seemed to kill the syncronisation process.

Thanks for your very prompt help on the matter too not quite a full fix but enough inspiration to keep going and try things to confirm other things were in fact wrong .

I got it down to where the remaining problem was mail stuck in the local smtp delivery Q but wasnt getting the last stage to some mailboxes. Running eseutil and insteg didnt fix that issue for whatever reasons I may never know.

Current plan - export all to pst's buy Exchange 2007 (SBS does seem a bit limited in some areas) and start again.

Glad you got somewhere. I would definately implement mailbox size limits, we have ours set to 250MB and use Symantec Enterprise vault to auto archive items to the EV server. Remember with Exchange Standard (don't know if SBS is the same) there is a size limit. It was 16GB on 2000, I don't know if it is higher in 2003/2007. I would advise your users to archive their older mail to a PST.
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