Chocolate and peanut butter. Baseball and hot dogs. Thelma and Louise. Some things just naturally belong together. To this list, you can add Microsoft Office Outlook and Microsoft Exchange Server.  Exchange supports many different clients, and Outlook will work in conjunction with any IMAP server (and many third-party MAPI implementations). But these two products are carefully designed to embody the Microsoft “better together” story in which Outlook, the premium Exchange client, delivers compelling features only when used together with Exchange.

Over the years, the value proposition of individual upgrades has varied somewhat. But the basic principle has remained the same: Microsoft giveth, and Microsoft taketh away. The combination of Exchange 2010 and Outlook 2010 is no different. Outlook 2010 contains many changes, some of which are tied to Exchange 2010 and some of which stand alone. The main question most people ask about every new Office release is, “What new features do I get?”

So this article focuses on what's new in Outlook 2010. (For a high-level look at the whole Office 2010 release, see “Office 2010 Not Resting on Its Laurels.") The changes in Outlook 2010 can be broadly grouped into a few specific categories:

  • Operational features; specifically, much better performance when starting and stopping Outlook, and some very welcome stability improvements in the Outlook IMAP implementation
  • Dropped features from previous versions, such as support for ANSI OST files (which I doubt anyone will miss), the ability to connect to Exchange 2000 mailbox servers, and computational postmarking for messages
  • New features that work together with any version of Exchange
  • New features that rely on the Exchange 2010 implementation

Although the first two categories are interesting, it's the new features that are really worth digging into more deeply.

 

New Outlook 2010 Features

With some Microsoft product releases, it’s hard to pick out just one favorite feature because there are so many choices. Outlook 2010 is a prime example of this because it has a lot of nifty new capabilities built in.

Multiple accounts per profile. Let’s start with something that Mac users running Entourage have been enjoying for a while: the ability to maintain multiple Exchange accounts in a single profile. Not everyone needs this feature. However, when you do—say, if you’re a consultant who needs to access both your company’s and your clients’ email systems—there really is no substitute. IMAP just doesn’t work as well (in Outlook or anywhere else) as the combination of Exchange and Outlook. Outlook 2010 proves this by allowing you to have up to 15 Exchange accounts in a single profile. The accounts have full access to all Exchange features, including public folders, search folders, and delegate access. Administrators can prevent users from copying messages between accounts by using the new HKCU\Software\Microsoft\Office\14\Outlook\DisableCrossAccountCopy registry subkey. If you specify the primary SMTP domain that you want to protect, Outlook will prevent users from copying messages from folders in that account to any other defined accounts (or to .pst files).

Calendaring. Calendaring has received some significant attention in this release. A new vertical Schedule View shows you calendars for multiple users in a large table view. Every user is a row, and every hour is a column. This orientation makes it very simple to see who is available and when. A related improvement: If you’re using an Exchange account, Outlook automatically provides you the option to see calendar data for your manager, for your peers, and for your direct reports, as defined in Active Directory (AD).

Conversation actions. Outlook 2010 has been justly praised for its improved “attention management” features, which Microsoft groups together under the rubric of “conversation actions.” The most notable of these features is the Ignore button (which has been compared to a mute button for email) and the ability to trim redundant messages from long threads by choosing the Clean Up command.

The Ignore feature depends on a new Outlook feature: conversation actions. There are three such actions: Ignore, Move, and Categorize. Conversation actions are stored in a hidden folder named Conversation Action Settings at the mailbox root. Every conversation that has a specified action will have an entry in this folder. You can see the entries by using MFCMAPI. Unlike server-side or client-side rules, only one conversation action can apply to a given conversation thread. This is because the actions are tied to a unique, per-conversation ID that is generated on the server. Conversation actions can be deleted automatically by the server after a preset time.

 

When you tag a conversation by using the Ignore button, messages in that conversation are automatically moved by the server to the Deleted Items folder. You can open an ignored message in Deleted Items, and then click Ignore again to deselect it. This deactivates the conversation action so that the conversation is no longer ignored.

By contrast, the Clean Up command works fine in any Outlook account, even in an IMAP account. This makes it handy for any account in which you receive many messages. When you clean up a conversation or folder, Outlook looks for duplicate message content. For example, let’s say that Alice sends a message to Bob and Carol. Bob replies immediately, then Carol replies to Bob’s reply. Outlook can safely delete Bob’s message because its content is included in Carol’s reply.

Quick Steps. Another new Outlook feature is its support for Quick Steps, which provide a simple, single-click interface for performing repetitive tasks. For example, you can configure a Quick Step to move messages to a particular folder that you use often. I have Quick Steps rules set up for my “pending orders” and “travel” folders. You can also create Quick Steps that take more complicated actions. I created one that marks the selected message as Read, moves it to a folder that I named “Action,” assigns it to a category, and flags it for follow-up. Follow these steps to create your own Quick Step:

  1. Start Outlook 2010. On the Home tab, click the dialog box launcher at the lower-right corner of the Quick Steps group.
  2. Click New, and then click Custom.
  3. In the Name box, type a name for the Quick Step.
  4. Click the Choose an Action down arrow, and then click Move to Folder.
  5. In the box that is displayed, click the Choose folder down arrow, and then select the target folder.
  6. Click Add Action, and then click Flag Message on the Actions list. You can select whichever flag duration you want; I use No Date.
  7. Click Add Action, and then click Categorize Message on the Actions list. You can select whichever category you want, or select Always ask for category if you want to be prompted. If you prefer, you can select a shortcut key and enter tooltip text in the Optional section.
  8. Click OK.

The completed Quick Steps dialog box is shown in Figure 1.

Because you can assign keyboard shortcuts to Quick Steps, you are likely to find that this single feature is one of your most frequently used. It simplifies the triaging of large volumes of mail.

In the same manner as conversation action settings, Quick Steps are stored as a list of commands in a hidden mailbox folder. In this case, the folder is named Quick Step Settings.

AutoComplete. The behavior of the AutoComplete addressee list is also changed. Previous versions of Outlook used a client-side .nk2 file that was specific to each computer. The .nk2 file contained the email address and display name of people to whom you addressed messages.

In Outlook 2010, these addresses are stored in the Suggested Contacts folder, a new contact folder that’s automatically created alongside your normal mailbox Contacts folder.

This new feature is both pleasingly useful and annoying. It’s quite useful to have the same set of address information follow you from computer to computer so that you get a consistent list of addresses no matter where you are. However, Outlook happily adds every recipient that you send messages to, even if they’re unsubscribe requests, responses to forum posts, or other transient addresses that you don’t want to keep. This is especially annoying for iPhone and iPad users because the Apple mail client doesn’t give you a way not to see the Suggested Contacts folder. You can turn this feature off by clearing the Automatically create Outlook contacts for recipients that do not belong to an Outlook Address Book check box in the Contacts section of Outlook options.

When you run Outlook 2010 for the first time, the program automatically tries to load your existing .nk2 file into Suggested Contacts. But that works only if your .nk2 file has the same name as the Outlook profile that you’re using. You can manually load an .nk2 file, but first you have to rename it to match the Outlook profile. Then, you must run this command:

outlook.exe /importnk2.

The one bad aspect of this particular feature is that Outlook 2007 and earlier versions don’t recognize the presence of the server-side AutoComplete list, so they continue to use .nk2 files.

 

One long-standing bane of Exchange administrators is that Outlook has been difficult or impossible to run safely on Exchange servers because the two products required different—and incompatible—versions of MAPI. Getting the right DLLs in the right places was difficult and error-prone. Back in ancient times, the Exchange client could be used for MAPI profile management on the Exchange server. But having Outlook installed on the server has ranged from unwise to flat-out impossible.

Outlook 2010 can be installed, and is supported, on servers that are running Exchange 2007 or Exchange 2010. In fact, if you’re using Exchange 2010 RTM, you must use Outlook 2010 to export and import mail to .pst files in Exchange 2010 for rediscovery and for mailbox import/export. However, Exchange 2010 SP1 completely changes how mailbox import and export work. So Outlook is no longer required on the server, making this feature less valuable than before. As a best practice, administrators shouldn’t be reading and responding to mail on an Exchange server anyway because of the risk of compromise from malware. If you have to read mail on the server, using OWA is a good workaround.

Outlook 2010 has a 64-bit version too, as does the rest of Office 2010. However, I don’t recommend deploying it for users just yet because the vast majority of Outlook add-ins are still 32-bit-only, so they won’t run in the 64-bit version. Also, the move to 64-bit addressing doesn’t provide any real performance or scalability benefits for Outlook users (as it does for Exchange itself).

User photos. The final non-Exchange-2010 feature I want to mention is one that you might have seen without realizing that it was new. Outlook 2010 displays pictures for users who have them. Pictures can come from individual contacts in your Contacts folders. If you add the thumbnailPhoto attribute to an AD user object, Outlook displays that photo for messages that are received from that user.

There are a lot of caveats to this feature. Chief among them is the fact that adding photos to your GAL adds considerably to  the size of the file. Pictures typically range in size from 9-15KB; multiply that by 10,000 users in a large GAL and you start to see the potential impact. Exchange 2010 can add these photos to the OAB. From here, Outlook 2010 can retrieve them when it runs in cached mode so that the photos are available when the Outlook user is offline. However, Outlook 2007, OWA 2007, OWA 2010, and the Entourage family of clients won't display the photo at all.

 

New Exchange 2010-Based Features

Remember what I said earlier about chocolate and peanut butter? The features that I've described so far work for any kind of account that you may have. But Outlook 2010 also includes several features that work only in association with an Exchange 2010 mailbox.

MailTips. Let’s start at MailTips. This is one of those features that makes you say, “Why didn’t I think of that?” The basic idea is simple: The Exchange Client Access server emits a warning message for certain conditions, such as if you address a message to a large distribution group. Outlook 2010 and OWA 2010 display the MailTips messages in a bid to save you from wasting time or embarrassing yourself. For example, you compose a message to someone who’s out of the office. Sure, you’ll find out about it when the message is delivered and you get the sender's out-of-office message—if they remembered to turn on the OOF feature. By using MailTips, you get an immediate indication when you compose a message to someone who’s out of the office. This lets you send the message to someone who will actually be able to act on it.

Among its capabilities, MailTips can warn you about recipients whose mailboxes are over quota, external recipients you might have mistakenly included on a message, or that you performed a “reply all” to a message that you received as a BCC. This feature may not sound that compelling on paper; but after you’ve used it, you’ll miss it if you have to revert to a client that doesn’t support it. Although you can define custom MailTips for individual mailboxes, there’s no way to extend them to permit new types of MailTips. One thing I hope to see in the future is an add-on for Outlook 2007 that will display MailTips. The MailTips information is available from the Exchange 2010 Client Access server, so it’s feasible to do this.

 

Voice Mail Preview. Exchange 2010 includes some major improvements to its unified messaging (UM) feature set. One example is the new Voice Mail Preview feature that translates spoken voicemail messages into text with surprising accuracy. (Although sometimes the surprise is what the transcription engine came up with for text!)  A complete list of supported languages is available in “Understanding Unified Messaging Languages”.

Exchange also delivers personal call answering rules that work similarly to the Outlook mail-handling rules, as you can see in Figure 2. Outlook 2010 provides a user interface for these features to display Voice Mail Preview transcriptions correctly. This enables you to edit call answering rules, although the interface for managing these rules is actually provided by the Exchange 2010 Client Access server. In the same vein, Outlook 2010 provides support for protected voicemail. By taking advantage of this Exchange 2010 feature, callers can mark as private any voice messages that they leave. The UM server uses AD Rights Management Services (AD RMS) protection to encrypt private messages. These messages can only be played back by using Outlook 2010 or Outlook Voice Access, neither of which allows private messages to be forwarded. Private voicemail messages, like other AD RMS messages, can be retrieved for discovery purposes, if necessary.

Figure 2: Personal call answering New Rule dialog box
Figure 2: Personal call answering New Rule dialog box

 

Personal Archive. The Personal Archive feature of Exchange 2010 represents another Microsoft shot across the bow of archiving and compliance vendors. This feature is designed to provide an easy-to-use, easy-to-manage solution for companies that have simple archiving requirements. Microsoft might be hoping that the Personal Archive feature will spell the doom of .pst files for most uses. That’s because the Personal Archive is essentially implemented as a secondary mailbox on the Exchange 2010 Mailbox server. In Outlook 2010, the archive is treated as a peer of your primary mailbox. This treatment means that the archive mailbox is easy to use. Users can drag items into and out of the archive at any time. However, unlike .pst files, the Personal Archive mailbox is stored on the server, so it’s accessible across computers. In fact, it’s accessible through OWA 2010, and Microsoft has committed to shipping an Outlook 2007 plug-in that makes Personal Archives accessible from that client, too.

Originally, this plug-in was expected in late 2010; but Microsoft recently announced a projected shipment some time in the first half of 2011.

SMS integration. Outlook 2010 supports integration with Short Message Service (SMS) text messages, too. At first this may seem like an odd feature, but it’s actually quite useful. You can configure Outlook to send and receive SMS messages in either of the following ways:

  • You can use a third-party SMS service. In this case, Outlook sends the SMS message to the service, and the service is responsible for delivering it to the recipient. Incoming messages may or may not be supported, depending on the service. However, incoming messages that the service delivers are synced to your Inbox in the same manner as regular mail messages.
  • You can use a Windows Mobile 6.5 or later device. In this case, when you send an SMS message from Outlook, Outlook passes the message to the Exchange server, which uses Exchange ActiveSync (EAS) to transfer it to the telephone. The telephone then actually sends the message as though you’d composed it on the telephone itself. In this case, EAS is also used to sync text messages from your telephone back to your mailbox. However, many users I’ve spoken to express horror at the idea that their SMS messages might be synchronized with their company email system, so you must consider privacy issues before you roll out this feature.

SMS integration with Outlook makes it easy to quickly send SMS messages without actually having to hunt and peck them out on your phone’s keyboard. Additionally, after you connect Outlook to an SMS service by using one of these two possible methods, Outlook can generate text messages that alert you about upcoming calendar events or that notify you about—or even forward—specified messages. 

 

An Ideal Partnership

The mechanics of licensing and deploying a new version of Office are not trivial—especially if you try to do that at the same time as you plan and deploy a new version of Exchange, of Microsoft SharePoint, or of Microsoft Office Communications Server. However, Microsoft has invested a lot of effort in making these products work better together.

Outlook 2010 is a compelling upgrade on its own, but it really shines in combination with Exchange 2010. I have been enthusiastically deploying Outlook 2010 everywhere I can. I strongly recommend that anyone who is planning a migration to Exchange 2010 include Outlook 2010 in the migration if at all possible. It’s that good.