Four synchronization issues between Outlook and site mailboxes

Site mailboxes are the brave new frontier for collaborative co-operation between Exchange 2013 and SharePoint 2013. You'll have to use Outlook 2013 Professional Plus to access the site mailboxes after they are created and then you might just run into some problems. At least, I have. But it's probably because I know little or nothing about the finer details of SharePoint and how document libraries work.

Site mailboxes provide a new collaborative interface between SharePoint 2013 and Exchange 2013 that’s intended to exploit the different strengths of the two products – document management for SharePoint and email for Exchange. Outlook 2013 Professional Plus is the only client that can currently access site mailboxes. The best laid plans of mice and men conspire to cause problems, so it’s unsurprising that site mailboxes have their little peculiarities, at least when viewed from the perspective of a long-time Exchange user. Here are some of the issues that I have encountered to date using Outlook to work with site mailboxes.

First, I attempted to add a document that already exists to a library. From the Exchange perspective this is somewhat odd. Exchange is quite happy to have as many items with the same name as you want in a folder. SharePoint isn’t and if you attempt to add a document to a library with a name of one that already exists, SharePoint prompts you whether you want to replace the existing item. However, when an item is added through Outlook, Exchange attempts to publish it to SharePoint through the background synchronization process and the attempt will be rejected. This might come as a surprise to the end user, so Exchange sends them a note (with the offending document attached) to let them know that a problem has arisen. In addition, the problem is noted in the Sync Issues folder of the site mailbox.

Here’s the text of a typical note:

Failed to upload the document How ActiveSync works.docx - Upload failed to SharePoint folder location at "https://contoso.sharepoint.com/Projects/Shared%20Documents/Books/Windows%20IT%20Pro%20Magazine". Following is detailed diagnostic information:

SharePoint ServerException - ErrorType:Microsoft.SharePoint.SPException; ErrorMessage:A file with the name Shared Documents/Books/Windows IT Pro Magazine/How ActiveSync works.docx already exists. It was last modified by i:0#.f|membership|tony.redmond@contoso as on 14 Jun 2013 04:18:17 -0700.; ErrorCode:-2130575257, ClientMachine:AMSPR04MB049

You could complain about the formatting and overly “nerd-like” language used in the text but it is relatively easy to see why the problem exists, but it is still a different way of working for Exchange users to get master. Let’s close that help desk ticket.

My next issue occurred when I attempted to delete a read-only document in a document library. Seems like a bad thing to do and so it is, but Outlook has no way of knowing that an item has been locked as read-only, as in the case when an item is checked-out by another user from a document library or if the item has been converted into a record. If you attempt to delete the item from Outlook, it first disappears and then comes back. Sounds odd? Well, behind the scenes Exchange attempts to synchronize the delete to SharePoint, which recognizes that the delete can’t happen because the item is checked out. So SharePoint rejects the delete and Exchange resynchronizes the item to make it reappear in the folder. All perfectly logical in a SharePoint kind of way…

My third issue is that when working in cached mode, I sometimes find that items from document libraries don’t synchronize as expected into the corresponding folders in Outlook’s OST (this problem was more pronounced in the past; it seems to be better recently). Before doing anything else, you should test that synchronization between Exchange and SharePoint is progressing normally. The best way to do this is to switch Outlook to work in online mode and then connect to the site mailboxes. If everything in the site mailboxes is visible you know that then problem is in the final step when Outlook synchronizes items from the site mailboxes into its OST.

The obvious fix is to use Outlook's "Update Folder" option to force synchronization to occur. Sometimes this doesn't work as it should (this might be an Office 365 gotcha). If all else fails, I’ve found that an effective fix is to use the “Manage All Site Mailboxes” option (available by right-clicking on the account name in Outlook’s navigation pane) to remove the site mailbox from the list of those displayed in Outlook, and wait for Autodiscover to remove the mailbox from the list of resources provided to Outlook. When this happens, Outlook removes the synchronized items for the site mailbox from its OST. You then go back to “Manage All Site Mailboxes” and select the site mailbox to be shown in Outlook. Autodiscover will then republish the site mailbox to Outlook and Outlook will resynchronize the mailbox contents from scratch.

# Update: March 11, 2014: I've found that synchronization occurs more reliably after installin Outlook 2013 SP1. Of course, the updates to Exchange and SharePoint on the server platform (in Office 365 or on-prem) might have helped too!

Finally, I have run into an issue where Outlook displayed all the contents of the site mailboxes but not using the normal document-centric view for items in document libraries. In addition, options such as “Manage All Site Mailboxes” or “Site Mailbox Properties” were not shown in Outlook’s right-click navigation pane menu. In this scenario all of the items in the site mailboxes appeared available to Outlook but communication with SharePoint was broken. For some reason, my Outlook client had become persona non grata with SharePoint. The solution was simple – revert to computer problem solving 101 and reboot the PC. After the reboot all was well and synchronization worked as expected.

All of this might sound like I’m complaining but I’m really not. I use site mailboxes for projects on a daily basis. Computer systems are often flawed, especially when a new feature (like site mailboxes) is introduced. Outlook attempts to construct a seamless collaborative face that masks the join between Exchange and SharePoint. Most of the time it does a pretty good job and I’m sure that the developers will make the interaction even better in the future. Happy collaboration!

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Tony Redmond

Tony Redmond is a senior contributing editor for Windows IT Pro and the author of Microsoft Exchange Server 2010 Inside Out (Microsoft Press) and Microsoft Exchange Server 2013 Inside Out: Mailbox...
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