Executive Summary:

Google's Gmail is becoming a more attractive email platform for businesses because it's a budget-friendly way to offload email management and storage to a third-party service provider. Learn how to use IMAP to connect Microsoft Office Outlook 2007, Microsoft Office Outlook 2003 and Microsoft’s Windows Mail and Windows Mobile clients to Gmail to gain a full-featured, popular email client with a high-quality, low-cost email server.


Google's free Gmail email application is popular with consumers because of its large mailbox quota (now more than 6.3GB and likely to increase over time), integrated antispam and antivirus protection, and powerful search capabilities. Moving beyond its consumer appeal, Gmail is becoming a more attractive mail platform for businesses—especially small-to-midsized businesses (SMBs) that find it cost-effective to offload email management and storage to a third-party service provider, rather than dedicate staff to onsite mail server administration. Gmail is part of the Google Apps suite that Google is selling to enterprises; the Premier Edition of Google Apps costs $50 per year per mailbox—an up-front cost that's much lower than traditional deployments of other messaging solutions, such as Microsoft Exchange Server or Lotus Notes.

One reason SMBs may hesitate to move their email to Gmail or another third-party web mail service is that they don’t want to give up the rich feature set of their Microsoft email clients for a less-sophisticated web mail client. Fortunately, you can connect a number of Microsoft mail clients—various Outlook versions, Windows Mail (Windows Vista’s free POP/IMAP client, a replacement for Windows XP’s Outlook Express), and Windows Mobile 6 email clients—to Gmail. Here I show you how to do so and also discuss interoperability considerations between different clients. Be aware that Google's iterative development means that Gmail and the other Google Apps change all the time. For example, Google recently added a new Gmail notification applet that installs into the Windows system tray. Thus, you should test Gmail in your own environment to determine its current level of functionality. The Gmail team's blog is a good way to keep track of recent developments.

Gmail Basics

Your first step to using Gmail is to sign up for a Gmail account at http://www.google.com/mail. A difference you'll probably notice right away about the web-based Gmail UI is that it doesn't use the traditional folder-based organization scheme that Exchange/Outlook, Hotmail, and other email systems use for messages. Instead, Gmail keeps all messages in a basic set of mailbox locations (i.e., Inbox, Drafts, Sent Mail, Spam, and Trash). Users who want to create their own organization scheme must create labels that they then use to mark messages. You can create whatever labels you like. For example, you might create a label for each of your current projects and one for personal mail. You can assign multiple labels to a message. After you assign labels to messages, you click the label to access the collection of messages that share the same label, much as you'd open a folder. However, labels aren't folders, and messages remain in their original location after you label them. In effect, you end up with a massive Inbox, albeit one in which you have a search capability that can locate messages in seconds.

If you use an IMAP client to access Gmail, you'll find that actions that affect the location of messages in IMAP folders cause Gmail to place labels on messages. Movement of messages in folders can occur explicitly, as when you refile a message, or implicitly, as a result of an action that you perform. For example, if you use the Windows Mail client to create and send a message, a copy of the message ends up in the IMAP Sent Items folder. Gmail treats all IMAP folders as labels, so the message automatically gets a Sent Items label that you can see if you use the Gmail web interface to view your mailbox. The same behavior occurs for messages sent using Microsoft Office Outlook 2007. You can think of Outlook's categories and Search Folders as having the same functionality as labels, but these features are less pervasive than Gmail labels.

The Gmail UI groups messages into conversations according to message subjects. For example, if you receive 15 messages with the same subject (e.g., "New Gmail feature"), Gmail lists one entry in the Inbox for the conversation called "New Gmail feature." When you open the entry, Gmail reveals all messages in the conversation, including messages that you sent and received. If you assign a label to a message, Gmail places the label on all messages in the conversation. (Outlook has an Arrange By Conversation view that groups messages in the same way).

Archiving is another concept that's slightly different in Gmail. In most email systems, the archiving process moves messages from the primary store to somewhere more suitable for long-term storage (e.g., moving messages from an Exchange server folder to a folder in a PST). Gmail wants to retain messages so that users can search them—hence the large mailbox size. So Gmail archiving means that messages are moved from the Inbox to a hidden location in the mailbox. However, you can always find archived messages through a search or by clicking the special All Mail view. In addition, if you click a label, Gmail displays any Inbox and archived messages that have the label.

The focus on labels and conversations and the lack of folders can take some getting used to for anyone accustomed to traditional email systems. For tips to help you understand how to use the Gmail interface, go to http://www.g04.com/misc/GmailTipsComplete.html.

Configuring Gmail

If you don't want to use the Gmail web interface, or if you prefer to use a more traditional email client to minimize user retraining, you can configure your Gmail account for IMAP or POP access, then use any of a number of email clients to access your Gmail mailbox. You have to enable your Gmail account for IMAP/POP access before you can connect a client. To do so, log on to your Gmail account, click the Settings link (top right corner), then click the Forwarding and POP/IMAP link to reveal the settings that control POP and IMAP access. By default, IMAP access is disabled, but POP is enabled.

Google offers adequate online information to help users configure different email clients to access Gmail, including training videos and user forums that contain useful hints and tips. For example, you can find instructions to configure IMAP access from Outlook 2007 to Gmail. Other articles describe general settings for POP and IMAP access from other popular email clients. Outlook 2007 and Microsoft Office Outlook 2003 can use IMAP, but older clients such as Microsoft Outlook 2000 and Microsoft Outlook 98 are limited to POP. Google provides a free tool for troubleshooting POP connections on Windows platforms.

Gmail's disdain for folders and the way that it uses labels mean that some internal translation is necessary to present data in the format required for IMAP clients. The Gmail server does this translation when a client uses IMAP to access it:

  • Labels become IMAP folders.
  • Messages appear in multiple IMAP folders if they have multiple labels. Incoming messages are in the Inbox and whatever folder that corresponds to their labels. Sent messages are in the Sent Mail folder and their corresponding label folders.
  • Conversations are expanded into individual messages.

When you understand how Gmail thinks of messages, figuring out how to make Gmail work through an IMAP client is reasonably easy. Another point to consider is that your search experience will vary depending on the client that you choose. Gmail's web interface includes typical search tools that let you search only your mail or the entire web. Outlook 2007 leverages Windows Search, and after you configure Gmail as a mail account, Windows Search includes messages in your Gmail account in its index, so that you can search across your Exchange mailbox, Gmail, and any other PSTs that you use. Windows Mail and other IMAP clients have their own search features, but they're unlikely to be as fast and comprehensive as those of Gmail and Outlook.

Configuring IMAP Access to Gmail for Outlook 2007

You can use Outlook 2007's Auto Account Setup feature to discover and set up a Gmail account. To do so, choose Account Settings from the Tools menu, then, on the Email tab, click the New icon to set up a new email account. You can then follow the directions to configure access to your Gmail account as I described in the preceding section. However, although Outlook can interrogate Gmail to discover some settings, it can auto-configure access to Gmail only for POP3 email accounts. Outlook 2007's auto-configure feature tries to connect to secure ports first, and if the attempt fails, it reverts to the default (unsecured) ports. This behavior may be why Outlook can't auto-configure IMAP access to Gmail; Google supports IMAP access only through secure ports. In any case, you can create the account manually and make sure that the settings are correct. Here are the essential IMAP configurations that you need to know:

  • Use Secure Sockets Layer (SSL) and specify port 993 for IMAP to imap.gmail.com.
  • Use Transport Layer Security (TLS) and specify port 587 for outgoing SMTP traffic to smtp.gmail.com.
  • Be aware that the outgoing SMTP server requires authorization and uses the same authentication as the incoming (IMAP) server.
  • Include @gmail.com in your account name (e.g., tony.redmond@gmail.com).

After you configure Outlook 2007 to access Gmail, you can send and receive messages. Outlook uses a PST to store Gmail messages, so the first connection might take some time to finish because Outlook has to download information about messages and labels from Gmail. After that, you can use Gmail as easily as you can use any other IMAP mail server. If you want to access Exchange and Gmail via Outlook so that you use Exchange for business mail and Gmail for personal communications, you can configure Outlook to access Exchange and Gmail concurrently and select which mail server to use to route outgoing messages, as Figure 1 shows.

Similar to other IMAP clients, Outlook synchronizes with Gmail to send messages and fetch any incoming mail that's waiting. Both Outlook and Gmail support HTML-format messages, so that reading messages originating in either system is no problem. For example, I cut and pasted this article's text (including the embedded figures) from Microsoft Word into an Outlook HTML-format message and sent it from Exchange Server 2007 to Gmail. The message arrived intact and looked fine in both Outlook 2007 and Windows Mail connected to Gmail. The same message lost some formatting (custom styles) when I viewed it through the Gmail web interface, but the message’s appearance was perfectly acceptable.

As you can see in Figure 2, when connected to Gmail, Outlook 2007 looks and feels as if you were connected to an Exchange server. From an end-user perspective, using Gmail with Outlook is fairly seamless—at least for basic email functionality. Client-side features (e.g., using the editor, sending and reading email, setting follow-up flags on messages, using contacts to address messages) work, but anything that depends on server functionality, such as setting an out-of-office notice, doesn’t work unless Outlook can communicate with the server to manipulate whatever settings are required to implement the feature.

Of course, many people use Outlook for more than email and value its personal information manager (PIM) functionality, such as contacts and especially the calendar. To export and import calendar data between Outlook and Google Calendar, you can use the iCalendar format (see http://office.microsoft.com/en-us/outlook/HA101674951033.aspx for details), but doing so is usually a one-time operation to move from one calendar type to another. If you want to access your Google Calendar from Outlook 2007, select Account Settings from Outlook’s Tools menu, click the Internet Calendars tab, then click New and enter a link to your Google Calendar. To get the Google Calendar link, open your Google Calendar and click Settings, then click the Calendars tab and then the calendar that you want to publish to Outlook (like Outlook, Google lets you maintain several calendars). Scroll down to the Private Address section and click the iCal button there to reveal the link that you need. Copy the link and paste it into Outlook when you're prompted to provide the link to the new Internet calendar, as Figure 3 shows.

After you've added your Google Calendar to Outlook, you can open the calendar and even display it alongside your Outlook calendar, letting you separate work (Outlook) and personal (Google) commitments, as Figure 4 shows. To keep the view updated, Outlook uses the same method that it uses for RSS feeds and SharePoint lists: Every 20 minutes, Outlook synchronizes in the background new items added to the Google calendar. Unfortunately, Outlook doesn't let you update items in an Internet calendar, so the Google calendar view is read-only. Third-party add-ons, such as SyncMyCal, are available to provide bidirectional synchronization, and this area likely will be a rich one for developers to explore as more enterprises become interested in using Google Apps. (For information about adding collaborative workspace and web access with Google Apps, see "Use Google Apps to Connect to Microsoft Office.")

Scheduling of meetings works well between Outlook 2007 and Google Calendar. If you add a Gmail user to an Outlook meeting, Outlook sends the meeting request in .ics format, so that Gmail recognizes it as a calendar item and lets the recipient read and respond to the request correctly. If the user accepts the meeting, Gmail sends a response to Outlook and adds the meeting to Google Calendar. The same is true for meetings created in Google Calendar. Notifications for these events arrive correctly in Outlook and are added to the calendar if the user accepts the request. The only problem that I had with scheduling was that Google Calendar occasionally failed to update after meeting acceptances arrived from Outlook into Gmail.

Even if you must do so manually, setting up Outlook 2007 to connect to Gmail is easy and works effectively. However, my experience using Gmail with Outlook 2007 was less seamless than using Hotmail. You can configure HTTP access from Outlook 2007 to Hotmail (or have Outlook configure access automatically), but Microsoft also offers the free Microsoft Office Outlook Connector, which provides a very smooth connection between Hotmail and Outlook 2007 or Outlook 2003. If you have a paid Windows Live subscription, you can use the connector to synchronize Outlook's calendar with your Windows Live calendar.

Using Gmail with Windows Mail

Apart from a new interface, there's little difference in functionality between Windows Mail and its predecessor, Outlook Express. Figure 5 shows the UI, which is straightforward and highly usable.

Configuring Windows Mail to connect to Gmail is easy, with the only complexity being the settings on the Advanced tab of the mail account properties in Windows Mail. To get to these properties, select Accounts from the Tools menu, select your Gmail account, then click the Properties button. Make sure that you specify the correct ports for SMTP and IMAP and that both are secure, as Figure 6 shows. After creating the right configuration, select IMAP Folders from the Tools menu and download the folder list from the Gmail server to complete setup for your mailbox. As with Outlook, any label in the Gmail account becomes a folder when viewed through Windows Mail. In Figure 5, the Cars, Finance, Knocksinna, and Mail Orders folders are all Gmail labels.

Gmail and Windows Mobile 6

You can find instructions for configuring IMAP access to Gmail for Windows Mobile devices at http://mail.google.com/support/bin/answer.py?hl=en&answer=78886. This configuration process is remarkably smooth because you provide only your Gmail email address and password.

I set up Gmail on PDAs running the Pocket PC and smartphone versions (Windows Mobile 6 Professional and Windows Mobile 6 Standard) of Windows Mobile, and both worked equally well. Windows Mobile connected to Gmail, set up my account correctly, and began downloading messages into Pocket Outlook. However, Pocket Outlook is the least effective of all the UIs. For example, after the account is created, Pocket Outlook synchronizes all items in your Gmail account (including deleted items from the Trash folder) rather than just those in the Inbox. In addition, all items are marked as unread. Windows Mobile is likely a minor target for Gmail developers, so the APIs available for Pocket Outlook are less well known than the IMAP APIs. These factors, along with Gmail's insistence on using labels instead of folders, combine to confuse people and make Gmail access from Pocket Outlook a fairly unproductive experience. You can use the Pocket Outlook/Gmail combination for email triage, but that's about it.

Gmail is also supported on other non–Windows Mobile devices. For example, the Apple iPhone has out-of-the-box support for configuring Gmail access via IMAP. The iPhone has other capabilities too. For example, you can chat with your Gmail contacts on the iPhone—an experience that's better on the 3G version than the original.

Smooth Mailing

Gmail is a powerful email server that supports millions of mailboxes. Although its web-based interface can baffle users accustomed to traditional folder-based email systems, you can use IMAP to connect Outlook or other email clients to Gmail to ease the learning curve and create what might be the best of two worlds: well-developed email UIs in popular clients with a good (and free or low-cost) email server.