Executive Summary: Microsoft Office Outlook is a useful application for messaging, calendaring, and scheduling, but not as useful for document management. Microsoft Windows SharePoint Services (WSS) and Microsoft Office SharePoint Server (MOSS) 2007 was designed as a content management platform but users hesitate to learn yet another new interface. With the integration points provided by Microsoft in the most recent Office release, you can use SharePoint and Outlook together to fully leverage the strengths of each product.

Microsoft Outlook has long been the center of Microsoft's collaborative user experience. Information workers rely on integrated messaging and calendaring to help manage their daily tasks. The result is that most users open Outlook first thing in the morning and shut it down only at the end of the day.

Although email is great for applications such as integrated calendars and scheduling, it's not as good for uses like document and content management. Your Microsoft Exchange Server administrators have a long list of reasons why sending large attachments through email isn't the best way to share documents. However, few of them offer reasonable alternatives that have low impact on your users' habits, and changing users' work habits, especially when those changes reduce convenience, is difficult. Enter Microsoft Windows SharePoint Services (WSS).

SharePoint was designed as a collaboration platform and therefore is a better medium for sharing content than any messaging system. However, one of its main flaws—and the biggest obstacle to getting organizations to deploy SharePoint—is its Web-based interface. Users don't want to learn yet another interface for managing their documents. It's inconvenient to pull up a Web browser and navigate to a specific site just to upload or download a file, when they can simply use Outlook and attach the file to a message. However, what if they could use that same familiar Outlook interface to access content in SharePoint? Read on and let me show you how to do it.

Using the Right Versions
The first requirement for using Outlook and SharePoint together is to ensure that you have the right versions. Microsoft offers the following main flavors of SharePoint products:

• WSS 3.0 is the most recent core SharePoint offering. It's built on ASP.NET 2.0 and free for download and deployment on Windows Server 2003.
• Microsoft Office SharePoint Server (MOSS) 2007 builds on WSS 3.0 and is the most recent enterprise-grade SharePoint product. It's suitable for large enterprises or external-facing deployments.
• WSS 2.0 is the previous SharePoint offering and is built on ASP.NET 1.1. It's still available as a free download for Windows 2003 and is included in Windows 2003 R2.
• SharePoint Portal Server (SPS) 2.0 is the previous enterprise-grade SharePoint product; it builds on WSS 2.0.

There are a few other variants of SharePoint, but they're built on one of these four products. The differences are negligible from an Outlook user's point of view.

At a minimum, you need WSS 2.0 and Outlook 2003 to get the benefits of integration. To get the best experience, you'll want WSS 3.0 and Outlook 2007. You don't have to use MOSS 2007 or SPS 2.0; both WSS 2.0 and WSS 3.0 will do the job.

You don't need a specific version of Exchange Server (or even use Exchange Server) to get Outlook and SharePoint working together. Outlook doesn't use typical messaging protocols such as Messaging API (MAPI) or SMTP to integrate with SharePoint. SharePoint alerts are the one exception to this rule: Alerts are email messages generated by SharePoint, so you need a working SMTP infrastructure.

Depending on which versions of software you have in your environment, you might not see the full benefits of integration. Table 1 shows the interaction capabilities between different SharePoint and Outlook versions. WSS 2.0 and Outlook 2003 offer a degree of integration, but most of it is one-way integration; Outlook pulls the data from SharePoint, but any changes made in Outlook aren't pushed back. Instead, you must use your browser to update the resource in SharePoint; the updated content is then replicated back to Outlook. Although this isn't ideal for many scenarios, it's good enough for many teams and projects and gives users the benefits of having ad hoc or team-based repositories that they can view from Outlook.

Note that if you use Exchange 2007 Outlook Web Access (OWA), your access to SharePoint data gets even better. You can configure Exchange 2007 OWA to proxy requests to specified internal SharePoint servers, allowing authorized users to reach content in SharePoint repositories by clicking embedded links in their messages, even when they're outside your firewall. Unfortunately, this isn't true if you're using Outlook. Although the Outlook Anywhere feature in Exchange 2007 lets you connect to Exchange from any Internet connection, it isn't a generic HTTP Secure (HTTPS) proxy. If you're outside your firewall and need Outlook to access SharePoint data, either your SharePoint servers must be published externally or you need some other solution such as a VPN connection.

SharePoint Content Available Within Outlook
The first thing you need to understand when using Outlook and SharePoint together is how SharePoint stores content. Although the SharePoint interface uses Web pages and sites, most SharePoint content is in the form of lists—calendar events, contacts, documents, and the like. The SharePoint interface is designed to help the user get to those all-important lists. Starting with WSS 2.0 and Office 2003, Microsoft provided integration points to allow Office applications such as Outlook to consume list content from SharePoint without the HTML wrapper. Figure 1 shows a typical SharePoint document list seen from the Web browser; Figure 2 shows the same document list accessed from Outlook.

Let's take a closer look at the types of SharePoint content you can consume in Outlook, as well as look at why you'd want to use SharePoint instead of Exchange or some other messaging system:

Document workspaces. Document workspaces are repositories for sharing documents. SharePoint offers several desirable document workspace features such as versioning and document check-in and check-out. Although many people use Outlook and Exchange public folders for ad hoc document management, public folders don't have the same features as SharePoint. Don't underestimate the productivity boost of knowing that you always have the most recent version of a given document at your fingertips. Outlook users can create shared attachments, which are stored in a dynamically created SharePoint document workspace as well as being sent as a conventional attachment.

Meeting workspaces. Meeting workspaces, such as the one that Web Figure 1 (http:// www.windowsitpro.com, InstantDoc ID 96624) shows, let you collect in one place all the typical types of content that you might find in a meeting. Outlook users can easily provision a meeting workspace while setting up the meeting invitation. Meeting workspaces offer features such as an agenda list, an associated document library, a task list, and a decision list. All invitees can access and update these, allowing any participant in the meeting to update the agenda or upload a relevant document without having to manually send the changes out to all participants.

Contacts. These are records that identify people with whom we interact. In SharePoint, contacts are typically shared by project or site; the contacts the IT team keeps will be different from the contacts the HR department keeps. SharePoint contacts are directly analogous to the Contact entries in Outlook and contain many of the same properties, as Figure 3 shows. By using a contact list in SharePoint, everyone who has access to the list has a single place to update the contacts, instead of having to maintain and swap Contact objects. You could also use public folders to share contacts, but then each recipient has to manually track the latest versions and update them.

Events. Events are records that describe appointments, meetings, or other calendar data. In SharePoint, calendar data is typically shared by project or site, providing a convenient tool for groups. Outlook users are familiar with calendar data, so having shared calendars for specific projects—and having those calendars automatically update—is a huge win.

Tasks. These are records that capture items that you're responsible for accomplishing, along with their due date, as Web Figure 2 shows. Both SharePoint and Outlook offer support for creating and assigning tasks, but a SharePoint task list is immediately visible to all users without having to manually send out and update the tasks. Outlook will remind you of SharePoint tasks that are due and show them in your calendar.

RSS feeds. These are XML files that describe Web-based content without formatting. They provide a way to subscribe to a content producer and regularly pull updates into the user's client of choice. Although you can modify WSS2.0 to provide RSS feeds, feeds are built into WSS 3.0 and are natively available for most types of lists. The ability to consume RSS feeds is a native feature of Microsoft Internet Explorer (IE) 7.0 and Outlook 2007. By leveraging this capability, you can consume practically any type of data stored in SharePoint beyond the types already mentioned. Figure 4, shows an RSS feed in Outlook.

Synchronizing Content
There are no special steps that you need to take to get Outlook talking to SharePoint; all the correct ActiveX controls are installed when you install Outlook. As you add SharePoint resources to Outlook, Outlook must track those resources. Both versions of Outlook create a separate PST file store on the local hard drive to hold the SharePoint content. Each separate SharePoint list is seen in Outlook as a unique folder within this new store. When new content is posted to the linked SharePoint list, Outlook copies it to the appropriate folder.

This synchronization design has several implications that you need to be aware of. First, whenever you launch Outlook, it automatically attempts to synchronize SharePoint resources. This is great when you have access to the SharePoint server because it allows you to view the latest version of your SharePoint resources when you're offline without having to manually fuss with synchronization. The downside is that if Outlook can't connect to your configured SharePoint resources, you'll see annoying authentication prompts and synchronization errors.

Because of this synchronization design, to keep automatic synchronization working, you must keep the folders in the SharePoint store. You can copy items out of these folders and into regular folders, but if you move the linked folders, Outlook will lose the link to SharePoint and will stop updating them. Likewise, any items that you copy or move from these folders won't be updated in their new locations.

Finally, the SharePoint personal store is unique to both the Outlook profile you're using and the computer you're running it on; if you use both a desktop and a laptop, you must add your SharePoint resources to both instances of Outlook.

Configuring Outlook
The process for using Outlook with SharePoint is simple. The following steps outline the general procedures for accessing and working with different types of content.

To access a SharePoint list:

1. Access the SharePoint list that you want to synchronize with Outlook.
2. Perform one of the following actions:
   • For WSS 2.0 and SPS 2.0 Contact and Event lists, select the Link to Outlook option in the list's header. See Figure 3 for an example of this option.
   • For most WSS 3.0 and MOSS 2007 lists, select the Connect with Outlook option under the Actions menu in the list's header.
3. Let Outlook synchronize with the SharePoint resources automatically.
4. Optionally, copy the SharePoint data to other Outlook folders as needed.

To link an attachment in Outlook to a SharePoint Shared Workspace:

1. Open the message and attach the file as usual.
2. Click the Attachment Options button, which Web Figure 3 shows.
3. Select the Shared attachments option.
4. Select an existing parent site under which to create the new Document Workspace or provide the URL of another parent SharePoint site.
5. Send the message.

To link an Outlook meeting invitation with a SharePoint Meeting Workspace:

1. Open the meeting invitation in Outlook. Enter the details and invite the attendees.
2. Click the Meeting Workspace button and specify the URL of the parent SharePoint site.
3. Perform one of the following actions:
   • To create a new workspace, leave
   the Create a new workspace option selected. Select the template language and template type from the lists.
   • To use an existing workspace, select it from the list.
4. Click OK to create the meeting invitation and create or link the meeting workspace.

Pain Points
Integration between Outlook and SharePoint isn't all roses. You need to keep in mind the following limitations:

• By default, WSS uses Integrated Windows Authentication, where the browser passes the credentials of your logged-in Windows account to the SharePoint server. Outlook can be used in a variety of situations that don't allow integrated authentication, so your users might need to enter their credentials to synchronize SharePoint content when they first start up Outlook.
• You must address backup and restore of your synchronized data because it's all kept in the special PST file. This store isn't backed up during the server-side backup processes on your messaging server, so you need to include it in the workstation-level backup processes you use. (Your regular SharePoint backup process takes care of the server-side data, so if you do lose this store it's not lost forever.) You also need to ensure that your Outlook profile is backed up, which is not typically the case in many Exchange environments.
• Synchronization between SharePoint and Outlook doesn't always happen as quickly as users would like. Although it's not a completely random process, SharePoint synchronization seems to happen as a background task. As you're working in Outlook, it will work through your configured SharePoint resources one at a time and update them. When you have a large number of updates, this can take a bit of time. If you're in a hurry and need to ensure that your SharePoint resources are fully updated, you can right-click the SharePoint store in Outlook and select the synchronization option.
• As mentioned earlier, unless you're using Outlook 2007 and WSS 3.0 together, any updates you make to replicated content in Outlook will need to be manually uploaded to SharePoint. Although this means you can't use Outlook as a complete replacement for navigating SharePoint in your Web browser, you can use it as an alternative for day-today tasks.
• The release version of Outlook 2007 has some problems with slow performance when the user's data store is larger than 1GB. Because one of the reasons people are using Outlook and SharePoint together is to enable Outlook to handle the bulkier document types without having them clog up the messaging system, this problem can be a pain point when using Outlook and SharePoint together. The Microsoft article "You may experience performance problems when you are working with items in a large .pst file or in a large .ost file in Outlook 2007" (http://support.microsoft.com/kb/932086) describes the problem and offers a hotfix to resolve the problem.

Other Resources
There are numerous resources for learning about SharePoint and Office. Many of them give excellent information on integrating SharePoint with Outlook and other Office applications. Here a few of the best ones:

The Office Online Web site (http://office.microsoft.com) is the first place to go for Office guidance. It provides many useful resources for Office users, including handy how-to guidance for many tasks.

One of your best resources for any version of Office is the appropriate Microsoft Office Resource Kit. These resource kits can be found online at http://www.microsoft.com/office/ork and contain a wealth of guidance to help you mange your Office applications and find ways to make them work better together. Whether you're using WSS 3.0 or MOSS 2007 product, most of the guidance will apply to both products.

The SharePoint team maintains a blog at http://blogs.msdn.com/sharepoint. It provides a fascinating and useful "behind the scenes" look at the SharePoint product. Many of the posts focus on administering SharePoint and using SharePoint through the Web interface, but the blog is a great contact point not only with the SharePoint product team, but with the regular crowd of SharePoint enthusiasts who participate through the comments.

Better Together
WSS is Microsoft's preferred collaboration platform for sharing and managing document and list content. Although it's grown steadily more useful with every version, offering greater degrees of interaction with the applications in the Office suite, many users and administrators fail to take full advantage of its true power because they find a Web-based interface to be too cumbersome or disruptive.

Outlook is a popular productivity application that helps users manage not just messaging data, but calendar and contact information as well. With the integration points provided by Microsoft, you can use SharePoint and Outlook together to fully leverage the strengths of each product. This kind of interaction can overcome some of the limitations of using the messaging infrastructure (such as Exchange Server) as a document dissemination and management medium, while still giving users a central interface for their daily information worker tasks.