To make Outlook the personal information manager for a wider range of users, Microsoft created an Outlook Hotmail connector that synchronizes Hotmail accounts with Microsoft Outlook. Although Hotmail isn't a corporate solution for messaging, I have seen companies offer and allow Hotmail use for their users. I have also seen Outlook users (where Exchange Server wasn't deployed) leverage web mail, such as Hotmail, to send work home. The Outlook Hotmail Connector brings Hotmail into the Outlook interface.

The most recent incarnation of this connector was released on May 4, 2010. Hotmail is now referred to as Windows Live Hotmail and the Outlook Connector is now at version 14.0. There are separate 32-bit versions of the Outlook Connector for Outlook 2003, 2007, and 2010 (32-bit version). There’s also a 64-bit version of Outlook Connector for Outlook 2010 (64-bit version), of course. You can download the Outlook Connector from the Microsoft download site:

This isn’t a third party add-on; it’s a Microsoft tool to connect a Microsoft application to a Microsoft web mail application. It uses a proprietary protocol, DeltaSync, which remains from the Hotmail Connector for Windows Live Mail (formerly Outlook Express). OutlookConnector.exe is just over 3MB to download and has a simple installation, as you might expect. You can even install the connector with Outlook open; however, Outlook will have to be restarted to engage the new connector. Enterprise application deployment mechanisms, including Group Policy or third-party solutions, can be used to push out the Outlook Connector to clients.

When Outlook is first started after installing the Outlook Connector, the Microsoft Hotmail Outlook Connector pop-up appears and asks if you want to add a Hotmail account, as Figure 1 shows.

Figure 1: The Outlook Hotmail Connector pop-up

Click Yes to open a new window where you can input your Hotmail account credentials. Figure 2 shows this window with Hotmail account credentials filled in.

Figure 2: Adding Hotmail account credentials

The Outlook Connector integrates well with the Outlook UI. The Outlook Connector adds a MAPI account for Hotmail to your Outlook profile. A separate .ost file is generated in the default location (\Users\<username>\AppData\Local\Microsoft\Outlook\<name>.ost) allowing you to access your Hotmail account even when you’re offline. The connector doesn’t allow you to change this offline folder's file location. New folders for the Calendar and Contacts, specific to Hotmail, are also added. The Calendar view is shown in Figure 3.

Figure 3: Hotmail Calendar view added in Outlook

The Outlook Connector allows your users to bring their Hotmail accounts into Microsoft Outlook, including Contacts and Calendar items. The connector is bi-directional; new items created in Outlook using the Hotmail account are automatically synchronized to the remote Windows Live Hotmail web account, and items created at Hotmail.com are automatically copied to the local account in Outlook as well. There’s more versatility having email, contacts, and calendar items stored in Outlook, including different views (like Business Card view for contacts or overlapping calendars) and programmatic access. The newest version of the Connector adds a few features and more control of Hotmail accounts through Outlook.

For the first time, the Drafts folder is now synchronized between Hotmail and Outlook. (I've seen users save contents to the Drafts folder for accessing at another location.) The Hotmail account can now be included in Send/Receive groups along with other Outlook accounts. Figure 4 shows the Hotmail account synchronization progress reflected in the Send/Receive dialog box along with other accounts.

Figure 4: Hotmail account synchronization progress

The connection status between Outlook and the user’s Windows Live Hotmail account is displayed at the bottom of the main Outlook interface, as Figure 5 shows.

Figure 5: Outlook and Hotmail connection status indicator

The most significant additions to the Outlook Connector fall into the category of message manipulation. First, you can now manage messages for your Hotmail account with rules within Outlook. If you create a rule in Outlook that affects an item in your Hotmail account, the output of the rule implemented in Outlook is also synchronized to Hotmail. The rule itself created in Outlook isn't synchronized, however. Only the resulting output of that rule is replicated to Hotmail. An example of such a rule might move messages upon arrival to a folder called Research within your Hotmail account. These messages will arrive at the Hotmail servers and into your inbox. The Outlook Connector will synchronize these messages, bringing them into Outlook. This will trigger the rule to move the applicable messages to the Research folder. After the message is moved to Research folder within Outlook, this move is then synced back up to the Hotmail servers.

Secondly, the safe sender, blocked sender, and safe recipient lists are now synchronized between Outlook and Hotmail through the new Connector. When a sender is added to the safe or blocked lists either in Outlook or in the Hotmail interface, the Connector syncs this addition. This extends more message hygiene measures across multiple interfaces. Figure 6 shows the lists in Hotmail, and Figure 7 shows them in Outlook.

Figure 6: Hotmail Safe Senders Options

These new content controls and interface changes really help make Outlook a more viable interface for Hotmail. You could actually maintain your Hotmail account, or allow your users to access theirs, without having to visit Hotmail.com (or mail.live.com).

Figure 7: Synced Outlook Hotmail Safe Senders Options