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Microsoft Exchange Server 2013 : Site mailboxes (part 1) - How site mailboxes work - Synchronization between Exchange and SharePoint

3/10/2014 9:26:21 PM
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Everyone will have his own definition of what collaboration means and how this can be achieved best within Exchange. Some believe that email (still the collaborative application par excellence) is good enough, provided it is used well. Others consider public folders capable of satisfying the needs of their organization. Many have invested heavily in SharePoint and are annoyed that Microsoft has not been able to connect Exchange to SharePoint in any coherent manner since SharePoint was first released in 2001.

Up front, the most important point to remember about site mailboxes is that they operate on the principle of keeping the content where it belongs. In other words, Exchange looks after email, and SharePoint takes care of documents. This is an appropriate and intelligent division because SharePoint is optimized for documents, and Exchange is not.

Public folders make excellent repositories for email discussions, but they are a pretty useless repository for document-based collaboration, such as when a group of people works together to author a document or presentation that will go through many editing cycles involving multiple contributors. This can be done by using email, but it’s hard to keep track of the many versions of documents that circulate as message attachments unless someone is designated as the editor in chief. It’s also possible to accomplish a collaborative authoring process by using public folders as long as great care is exercised over when different users access the document to update its content. Unfortunately, humans are often not so good at exercising the necessary care.

Site mailboxes are designed to fill the gap by using the strengths of Exchange (for email) and SharePoint (for document management). In effect, a site mailbox creates a virtual container that includes a shared mailbox and the document libraries on a SharePoint site. A SharePoint site is a website hosted by a SharePoint server that is identified by a virtual URL. Each site can be configured with different SharePoint components to create whatever functionality is required by the site’s users. A site mailbox is an example of a component that can be added to a SharePoint site; tasks, calendar, and wiki apps are other examples.

The shared mailboxes created by the site mailbox app are fully functional mailboxes that have email addresses. The ability to accept email means that the site mailbox can be used as a form of email archive for the project if you add the site mailbox to any distribution groups used for project team communications. Each mailbox contains default folders such as the Inbox and Sync Issues, a folder that is particularly important because it captures problems that occur when Exchange and SharePoint swap information.

A synchronization process creates, populates, and maintains folders in the mailbox to represent the contents of the SharePoint document libraries that are associated with the site. Appropriately, these folders use a document-centric view to display their contents through Outlook rather than the conversation-centric view normally used for email messages in other folders. You don’t realize where the join exists between Exchange mailbox folders and the folders populated through synchronization with SharePoint because Outlook creates the impression that all the information in a site mailbox is held in one place. The fact that two servers work together to manage the site mailbox is immaterial to users. People never worried that old-style public folders used a completely different database and replication mechanism from Exchange mailboxes, so why should they worry that some items are in an Exchange mailbox and some are in a SharePoint site? The point is that they have access to the information they need to perform a task.

Two obvious dependencies leap off the page here. You need to deploy SharePoint 2013 to support the sites, and you need Outlook 2013 to be able to create the invisible join between mailboxes and sites. No other client is currently capable of accessing site mailboxes. Companies might well be considering a deployment of Outlook 2013 alongside Exchange 2013 because this version of Outlook exposes all the functionality in Exchange 2013, but a SharePoint deployment might represent more of a barrier to overcome. Deploying SharePoint requires additional investment in hardware, expertise, and software, and these factors have to be taken into account in any discussion about site mailboxes.

Nevertheless, assuming that all is well, that software and hardware have been procured and deployed, and that SharePoint and Exchange are both humming along like a well-tuned engine, the question of functionality is the next topic of discussion.

1. How site mailboxes work

The steps required to implement site mailboxes are described on TechNet and in many other web articles and do not need to be repeated here. In summary, the deployment of site mailboxes depends on:

  • Exchange 2013 mailbox servers to host the shared mailboxes associated with the SharePoint sites on which the site mailbox app is installed.

  • A SharePoint 2013 farm (or standalone server) to host the SharePoint sites that contain the document libraries and membership lists that are synchronized with Exchange and combined with the shared mailboxes to form site mailboxes. The SharePoint servers that host the sites and the Exchange servers that host the mailboxes must be on the same premises (on-premises or cloud), whereas the personal mailboxes of users can function cross-premises. In other words, an on-premises Exchange user can access site mailboxes that are stored in Office 365.

  • Outlook 2013 clients to present a single user interface to the site mailboxes that include both the Exchange shared mailbox and the SharePoint document libraries.

  • Exchange Web Services (EWS) and SharePoint representational state transfer (REST) application programming interfaces (APIs) to synchronize information between Exchange and SharePoint.

A considerable amount of work and cooperation is necessary between the Exchange and SharePoint administrators to configure the products to work together smoothly to enable the creation and operation of site mailboxes. Do not anticipate that this work can be done without preparation.

SharePoint communicates with Exchange using EWS, which means that you must download and install EWS on your SharePoint servers. It is important for a matching version of EWS to be installed on the SharePoint servers so they can communicate with the mailbox servers. In other words, if the mailbox servers run Exchange 2013 CU2, a matching version of EWS should be installed on the SharePoint servers.

Membership information (both users and owners) for the site mailbox is maintained through SharePoint. Users are permitted access to site mailboxes by being added to the membership list of the SharePoint site. Users have to be added individually because gaining access through group membership is not supported. In addition, users must have an Exchange mailbox, and that mailbox has to be on an Exchange 2013 server before they can use site mailboxes through Outlook. Users who have not yet been moved to Exchange 2013 can still interact with site mailboxes by opening the SharePoint site with a browser.

Behind the scenes, SharePoint synchronizes the membership list with Exchange to grant members full access rights to the shared mailbox. Like all other operations affecting the life cycle of a site, provisioning and updates for site membership is controlled from SharePoint, and Exchange does not proactively query SharePoint to discover new site members. After full access has been granted, Autodiscover adds the shared mailbox to the list of resources available to Outlook the next time it queries Exchange for this information, and Outlook opens the shared mailbox as soon as the new resource becomes known.

Outlook 2013 Professional Plus is the only client currently capable of displaying the site mailbox data about document libraries that Exchange retrieves from SharePoint. An Outlook Web App–like interface is available to the email items in a site mailbox if you click the Mailbox link when accessing the SharePoint site in a browser; this invokes an explicit logon to the site mailbox. However, unlike Outlook, Outlook Web App does not include site mailboxes in the set of available resources a user sees when he accesses his personal mailbox, and there are no public plans to change this situation. By comparison, Outlook considers a site mailbox like any other resource available to a user—like a shared mailbox, archive, or PST—so moving information into a site mailbox is as easy as dragging an item from another Outlook resource. In effect, anyone who knows how to work with Outlook can work with a site mailbox, which reduces the cost of deployment and support.

Items can be added to the site mailbox through SharePoint or Outlook by dragging and dropping items into the folders in the document library within a site mailbox or the other (regular) folders in the mailbox. It’s best to maximize the relative strengths of Exchange and SharePoint by putting email items in email folders and documents (such as those received as attachments to messages) into document libraries. This approach means that you’ll be able to use features such as threaded conversations for the messages stored in the site mailbox’s Inbox and version control for the items stored in the document library.

The content stored in site mailboxes is indexed and discoverable by eDiscovery searches. This is because Exchange 2013 shares the Search Foundation technology with SharePoint. Email has long since been indexed and discoverable; Exchange 2013 and SharePoint 2013 combine to make the documents held in site mailboxes discoverable, too—a fact that will surely bring joy to lawyers.

Site mailboxes are mail-enabled objects and behave in the same way as mail-enabled public folders. In other words, you can add a site mailbox as an addressee to a message, and Exchange will route the message to the Inbox folder in the site mailbox. Site mailboxes appear in address lists and can be hidden by setting the HiddenFromAddressListsEnabled property to $True. This step is usually taken to prevent users from including a site mailbox in messages when the mailbox is being decommissioned. Messages can still be sent to the site mailbox by using its Simple Mail Transfer Protocol (SMTP) address.

Set-Mailbox –Identity 'Project Alpha' –GrantSendOnBehalfOf 'Paul Robichaux'

The Send As permission can also be assigned for a site mailbox. In this case, you use the Add-AdPermission cmdlet. For example:

Add-AdPermission –Identity 'Project Alpha' –ExtendedRights 'Send-As' –User 'Tony Redmond'

SharePoint documents stored in site mailboxes remain in place when you add them as attachments to messages. A link is added to the message to enable recipients to access the content, but the documents stay in SharePoint rather than being circulated as attachments. It makes perfect sense to have a single definitive source for a document that’s intended as a collaborative object as long as the recipients have sufficient network connectivity to access the document when they need to. (The old replication model for public folders, although derided by many, at least had the singular advantage of making content available close to users.)

Items stored in site mailboxes are not subject to Exchange retention policies. All the information held in the site remains under the control of the SharePoint information policy that applies to the site. However, items in a site mailbox can be placed on hold using the SharePoint eDiscovery Center.

The stub items that represent the content of the document libraries can be synchronized down to the client OST like the contents of other mailbox folders if you select the Download Shared Folders check box on the Advanced tab of your Outlook profile. If not, Outlook makes an online connection to the shared mailbox when you want to work with its contents. Remember that only the stub items are synchronized. The actual content of document libraries always remains under SharePoint control. These stored documents can be made available offline by synchronizing the site to create a local copy of the document library on the PC. And, of course, you can always download a local copy of an individual document from SharePoint for use offline.

Synchronization between Exchange and SharePoint

Exchange synchronizes with SharePoint by using the SharePoint REST API to fetch the metadata used to display information about documents stored in the site mailbox, including document title, author, last modified date, checked-out status, and the user who last modified the item. Information held in the documents library is synchronized and presented alongside all the other folders in the site mailbox so that the data from the two sources seems as though it originates from a common repository. Items added to a document library through Outlook appear in italics to indicate that the synchronization is not yet complete. In other words, the item has been added to the Exchange mailbox but not yet copied (or published) to SharePoint. After SharePoint has accepted the item and stored it in the document library, the italics are removed and not displayed by Outlook.

If you add more than one document library to the SharePoint quick launch menu, Exchange will synchronize the items from each library into a separate folder. As used in the example discussed here, the default name for a document library on a SharePoint site is Documents, and this is the folder name seen in Outlook. The library could also be called Shared Documents, Project Documents, or whatever other name you assign to it.

In general, the synchronization process between Exchange and SharePoint is reasonably fast, and new items added through one interface appear in the other soon after they are added. If you add a new document library through SharePoint, it will soon appear as a folder in Outlook. Likewise, if you drag an item from Windows Explorer or File Explorer and drop it into the Outlook folder, the item will be synchronized to the SharePoint site within a few minutes. The same is true if you drag and drop items from other Outlook folders into the site folder. You can even create a subfolder for the site folder in Outlook, and it synchronizes with SharePoint. Items placed in the subfolder will also be synchronized with SharePoint. All of this works very well and makes the site mailbox a very approachable repository for anyone who knows how to work with Outlook. The sole downside is that you cannot drag items out of any folder that is synchronized with SharePoint to Windows Explorer (or File Explorer) or another Outlook folder; traffic is unidirectional—into the folder. In addition, if you forward or otherwise reference an item shored in a synchronized folder, the item is not sent as an attachment. Instead, a link to the SharePoint site is embedded in the message to allow the recipient to access the content by clicking the link.

Synchronization is user-driven. In other words, although information about a new site or document library or changes to site membership need to be updated as quickly as possible, information about the contents of a document library might not be so time-critical, especially for document libraries that are not updated very often. To make sure that Exchange and SharePoint remain synchronized, a timer job runs on the Exchange mailbox servers every six hours to make a request to SharePoint for information about new members, documents, and so on. However, if a site is actively used (documents or members are added), Exchange synchronizes with SharePoint every five minutes, and if a site is open in either SharePoint or Outlook, synchronization occurs every fifteen minutes even if items are not added or otherwise updated.

Failure of items to appear in a timely manner in either Exchange or SharePoint is an indication that something is wrong with the synchronization process. If this happens, you can check the last synchronization status by selecting the site mailbox in Outlook. Right-click it and select Site Mailbox Properties from the menu. This leads to a webpage (using EAC) that shows information about the site mailbox, including a Sync Status option. Here you’ll find the date and time of the last successful synchronization together with any error messages plus options to start synchronization. A useful Email Me Details option is provided that requests Exchange to send you a message containing some diagnostic information about the synchronization.

Inside Out SharePoint document name limitation

Exchange is perfectly happy to have multiple items with the same name in its folders. SharePoint is not so happy because it requires documents to have unique names. If you attempt to add a new item to a document library from Outlook, and the item already exists, everything will seem to be okay for a moment until SharePoint realizes that Exchange is attempting to publish an item that it cannot deal with. SharePoint will then drop the item and send the equivalent of a nondelivery notification (including an attachment with the failed item) back to the user to tell her that a SharePoint Server Exception has occurred because “the document already exists.” The failure is also noted in the Sync Issues folder of the site mailbox. The solution is to copy the item to Windows, rename it there, and then drag and drop the renamed file into Outlook. SharePoint will be much happier when Outlook synchronizes with the document library, and all will be well. The process is not perfect, but it works.

Information about each document is stored as properties of a stub item in the folder used to represent the document library in the site mailbox, including the URL pointing to the item in SharePoint. If you examine the contents of the Documents folder by using MFCMAPI, you can see the properties of the SharePoint items that Exchange synchronizes. When Outlook connects to the site mailbox, it retrieves data about email items from other folders as usual and uses the stub items in the Documents folder to construct the view of the information held in SharePoint.

Using stub items enables Outlook to have faster display access to items in the document library. When Outlook needs to retrieve content for an item held in SharePoint, it passes the URL of the item to the native application for the item. The application checks the Office Document Cache to determine whether an offline copy exists or whether it needs to retrieve a copy from SharePoint. A local copy might exist in the PC’s local cache or because of a previous synchronization with the document library to create an offline copy. When the correct location for the content is determined, the application retrieves and opens the item. As far as the application is concerned, it has received a request to open and process content and does not care about its source. Although it is usual to store mail messages in Exchange rather than in a document library, you can move messages to a document library for purposes such as marking the messages as immutable records. Messages are stored in document libraries as .msg files, and Outlook opens these items. Logically, if you open an item such as a Word document or a PowerPoint presentation that is checked out to another user, you will not be able to update the content.

Inside Out Synchronization only goes so far

You are probably used to the per-item read status map Exchange maintains to show users which items they have viewed and which they have not within a folder. Synchronization to make items in a document library visible to Outlook does not preserve such a status. For instance, if you add a new item to a document library in SharePoint, Exchange will subsequently synchronize it, and it will appear as an item in Outlook. However, the item is bolded, which is the normal convention that indicates a new item in a folder. The item is new to other users, but it’s certainly not new to you because you just added it to SharePoint.

Figure 1 shows how items in a site mailbox are accessed through Outlook 2013. In this case, a site mailbox called Project Alpha is open. The Inbox, Deleted Items, and Junk Email folders are stored in a mailbox database that Exchange manages. The view of items in the Documents folder is constructed from the stub items. The properties synchronized to the stub items from SharePoint are sufficient to present an informative view to the end user.

An annotated screen shot showing how Outlook displays the items in the Documents library from a site mailbox called Project Alpha. The items in the Documents folder have been synchronized from the library on the SharePoint site.

Figure 1. How Outlook 2013 displays a site mailbox and its contents

If you run the Get-MailboxFolderStatistics cmdlet to report on information held in a site mailbox, it reports the number of items and the size of the items held in the Documents folder. The number of items is correct, but the item size represents only the much smaller stub items that hold the properties describing the real documents that are synchronized from SharePoint.

Because Outlook provides the interface for site mailboxes, some of the advanced document management features available within SharePoint are not exposed. For example, you can’t see prior versions of documents that are stored on the SharePoint site with Outlook, and you can’t check out a document to reserve it against editing by other users. These features are available by connecting to the underlying SharePoint site with a browser. The easiest way to access the underlying site for a document library is to select the library in Outlook, right-click it, and select Open In Web Browser from the menu. Figure 2 illustrates the situation after you have connected to the same Project Alpha site as accessed through SharePoint through a browser. The same items Outlook presents in the Documents folder are visible, but now some additional options such as document checkout are available because the web interface supports the options.

A screen shot of the contents of the documents library on the SharePoint site accessed through Internet Explorer. The same items are present, and extra processing options are available through SharePoint.

Figure 2. The same site viewed through Microsoft Internet Explorer

Accessing information about site mailboxes from Outlook

If you right-click your mailbox name at the top of the folder list, you see Manage All Site Mailboxes listed in the menu. Selecting this option causes Outlook to make a call to EAC to display the My Site Mailboxes page, listing the site mailboxes to which you have access. The list is displayed on a webpage rather than by Outlook. The following fields are shown:

  • Show In Outlook. Typically, this check box is selected, meaning that Outlook should open the site mailbox and display its contents. If you clear the box, the site mailbox will be removed from the Outlook list of resources. Selecting the box again restores matters, and the site mailbox will reappear.

  • Name. This is the name of the site mailbox.

  • Your Role. This will be Owner if you created the site mailbox or Contributor if the site mailbox has been shared with you.

  • Active. This is a flag showing whether the site is still active.

The details pane for the selected site shows the SMTP address of the site mailbox, the URL to the SharePoint site, the list of owners, and the number of members. If you click a site, EAC retrieves and displays status data for the site. You can discover the current synchronization status and the list of users who have access to the site here.

Inside Out How many site mailboxes can Outlook open at one time?

Outlook 2013 is restricted to opening a maximum of 10 site mailboxes. The limitation exists for both usability and performance reasons. Having more than 10 site mailboxes listed in Outlook would make navigation very unwieldy and impose a large performance penalty on the client. Ten seemed to provide a good balance between the desire to make information available to users and the need to maintain performance. Exchange imposes the limitation by restricting Autodiscover to being able to include only 10 site mailboxes in the manifest that it returns to Outlook, so Outlook never knows that more site mailboxes might exist. If you have access to more than 10 site mailboxes, you can choose the mailboxes to open by choosing Manage All Site Mailboxes as previously described and selecting whatever mailboxes are required. After a short pause to allow Autodiscover to update Outlook, the selected mailboxes will appear in the resource list. Alternatively, select a site mailbox that you do not want to access anymore, right-click it, and select Close Site Mailbox from the menu. The site mailbox remains intact, but Outlook will no longer display it to you, again after a short pause to allow Autodiscover to update Outlook. A site mailbox that has been closed can be reopened by choosing Manage All Site Mailboxes.

Site mailboxes and Office 365

Site mailboxes are also available in many of the Office 365 plans Microsoft offers. Office 365 tenants might find it easier to adopt site mailboxes, if only because Microsoft takes care of all the heavy lifting to deploy and manage Exchange Online and SharePoint Online. All the tenant has to do before she can use site mailboxes is make sure that she uses Outlook 2013. In fact, the easiest way to review the functionality of site mailboxes and assess whether they offer value to your company is to take out a 30-day trial for an Office 365 plan that includes site mailbox functionality and use that tenant domain to test how site mailboxes work.

 
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