Outlook 2011 on Mac – Server Synchronisation issues / anomalies

We have an issue with Outlook 2011 and Exchange.

Basically we have a user who complained that what she filed on Outlook for the Mac and her iPad were not matching.

Long story short it turned out that all the email filing being done on Outlook 2011, was not being reflected back up to the server. However Outlook 2011 was reporting, “All folders up to date” and was receiving new email.

We downloading her profile again and broke the news about needing to re-filing. However about 3 days later we are in the same position. Therefore, although all appears to be good, about 500 emails are showing as being in the inbox on the server, however on the local Mac Outlook 2011, they have already been filed.

Does anyone have any insights about how we could force a sync from the Mac Outlook 2011 onto the server?
IT Man200Asked:
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Kash2nd Line EngineerCommented:
2011 Mac Outloook is crap.
I have had so many issues with it specially with exchange.
It never syncs properly.
There are some things you can try but make sure you make a backup copy of her emails which are in the outlook profile.

I would normally do the following:.
1. Make a backup of user identities folder (microsoft user data in docs on the mac).
2. delete the profile off outlook completely.
3. make sure office for mac is fully updated.
4. delete microsoft user data (after taking the backup)
5. reconfigure the profile and let it sync.
6. if possible make sure the user is in the office wired in so that it can sync quick enough.

good luck
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IT Man200Author Commented:
Appreciate the comments, but sadly nothing here that we have not already tried.
In this particular instance we want to avoid having to file the 500 emails again.

Do you (or anyone) think there is a way of taking what she has already filed (which only shows on the local computer) and forcing this to sync, without having to manually file again.
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Davis McCarnOwnerCommented:
How is the account setup on the Mac? (pop, IMAP. etc)
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IT Man200Author Commented:
It's an exchange setup as mentioned at the start. Thanks
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Davis McCarnOwnerCommented:
While this is listed as "not verified", check this:
http://www.officeformachelp.com/outlook/faqs/faqs-2/#modifyRegistry
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IT Man200Author Commented:
Interesting link. That particular point that you mention I think refers to changing a registry entry on the server. Sadly as this is a hosted exchange provider, we would not have access to the server to do this.

But this is an interesting link overall. Welcome any other suggestions about how we can approach this.

We thought about doing the filing for her via webmail to get it matching what she currently has on her computer. however, it's very difficult to find where a particular email has been filed to. Although we can find it when searching for it, we can't work out what folder it has been filed to.

Anyway, still open to any suggestions that solve this.
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Davis McCarnOwnerCommented:
Just above it (#2 FAQ) were instructions for emptying the cache so the sync would rebuild itself.  Have you tried that?
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Kash2nd Line EngineerCommented:
if its an exchange account, are you not able to see the folder structure in OWA and the emails that were filed in it.

If they aren't there then I am not sure there is any way apart from resenting to backup
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IT Man200Author Commented:
The folder structure can be seen on Outlook 2011.

Most of the folder structure can be seem on OWA, but the last 500 emails that were filed, on OWA they show in the inbox.

On Outlook 2011, they have been filled into folders.

So they are showing different views.

New email that come in, still come into the inbox and even, can still be filled if carefully done.

But there are 500 not filed.

If we download the mailbox again, the user will have to refile those 500 emails.
Does that make sense?
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Davis McCarnOwnerCommented:
Yes; but, I don't think you have any other real options.  If you don't get the syncing working again, it will soon be thousands of emails in the wrong place!
What version of Exchange is it?
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IT Man200Author Commented:
Belated response. But this problem still goes on. I buried my head in the sand, but end user kept digging it up and shouting.

But we have got it to the point where we can rebuild a new profile within 24 hours. This is not bad.
however, sync stops working almost right away.
Particularly sent items.
So as soon as the users syncs some items, it breaks right away.

the exchange version is 2010. Our exchange provided mentioned to moving to a new DB, but I'm not sure what they mean by that and I'm awaiting response.

I'm considering migrating to Exchange 2013 backend, but this is a bit of an ordeal, but do you think it makes a difference?

Also Outlook 2016 is just out, but as part of this process, we even purchased a new Mac for the end user. And we bought a one off licence for Outlook 2011. They would be too pleased to have to go and buy Outlook 2016 just after buying Outlook 2011. So stuck with that for now.

(Yes I know O365 gives you free upgrades but they are not our exchange provider so don't want the conversation to go down that road)

Many thanks  so far.
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Davis McCarnOwnerCommented:
You could set her up as IMAP and be done with it:
http://blink.ucsd.edu/technology/email/tasks/clients/outlook2011-imap.html
Afterwards, ALL of the changes and manipulation would be on the server.
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IT Man200Author Commented:
Don't think I could face IMAP. What about contacts and calendar etc. Exchange is meant to be on the server like IMAP right?
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Davis McCarnOwnerCommented:
If they ever sync'ed (especially recently), the contacts and calendar ought to be there.  AFIK, OL 2011 is primarily an offline app meaning it downloads to local storage rather than working directly on the server.
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IT Man200Author Commented:
Still no joy with this really. I'm trying a few things with support, but going on a long time.
I will likely close this case soon.
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