In a previous post, I described how to synchronize a Gmail calendar with Outlook 2010 using the IMAP email protocol. This post will describe how to create an Outlook profile that will support multiple IMAP Gmail e-mail accounts, a contact list and calendar synchronization.

For a number of years, I’ve used the email domain of a well-known cable company to host my personal as well as business email. Unfortunately, the cable company’s e-mail system only supports POP3. With a web-based e-mail system, keeping your email synchronized among many computers running Outlook is problematic when you use multiple computers such as you desktop at work or at home and perhaps, a laptop.

The Problem

The POP3 protocol delivers mail to the client computer that requests delivery and by default removes the message from the mail server. The paradigm that client delivery programs are based upon a person, going to the mailbox to pick up the mail. The messages are no longer in the mail box but are physically in the hands of the person, client program that retrieves the message. It’s possible to circumvent this behavior using Outlook by enabling the setting found in the Account Settings | Internet E-mail Settings | Advanced tab | Delivery setting. Just check the box labeled “Leave a copy of messages on the server” and optionally check “Remove from server after XX days” and or “Remove from server when deleted from ‘Deleted items’.” The trick is that you have to do this on all of the computers using Outlook to connect to the mail server. Otherwise, mail disappears from the web client and is automatically delivered to the computer lucky enough to be the first one checking the mail server for new mail.

Well, that’s not so bad. You learn from your mistakes. However, what is very frustrating is the fact that “Sent Items” is local to each computer running Outlook and the web. Say you respond to an e-mail, using your browser, the copy of the message is on the server’s “Sent Items” folder. When you reply from one of your computers and the e-mail reply is in the Outlook “Sent Items” folder on that computer. To circumvent this behavior, you can BCC yourself on the reply. This will send the message to the intended recipient but will also send the message to your Inbox. At least with this method, you can see the reply to the original message from any of your computers. By the way, don’t make the mistake of replying to the BCC’ed email because it will come right back to you. Wait for a response from your response before using the same BCC technique to respond. This gets the job done but after a while it’s no longer fun but merely tedious.

The Solution

The solution to “POP3 / PST Hell” is Microsoft Exchange or E-Mail using the Internet Message Access Protocol (IMAP). IMAP is a protocol that’s similar to Exchange’s Message Access Programming Interface ( MAPI). The protocol automatically leaves a copy of your message on the mail server. Using IMAP, the “Sent Items” folder on the mail server will contain a copy of all outbound e-mail and when you use Outlook to connect to your account, you see exactly what is on the server. This eliminates the problems described above using POP3.

You can add one or more Gmail IMAP accounts to your Outlook profile. Remember to enable IMAP in your Gmail account settings beforehand. By default, Gmail is configured to use POP3. You can disable it and if you choose, connect using POP3. You can also activate the setting to keep messages on the server. The important thing to remember is to enable IMAP. In Gmail, go to the Settings | Forwarding and POP/IMAP section. Click the button to “Enable IMAP.” In addition, you can get explicit instructions in the help links on the page.

Data Files

Just like using POP3, Outlook creates PST files with an IMAP account. The first file created in the profile is in in the “My Documents\Outlook Files” folder and is named “Outlook Data File – <profile name>.pst”. If your profile is named “Gmail”, then the file that’s created is called “Outlook Data File – GMail.pst”. This file is the one that contains your calendar and contacts. It’s the same type of pst file created using Exchange or POP3, except it doesn’t contain any messages.

A file is created for each account in the profile and is placed in the “C:\Users\<username>\AppData\Local\Microsoft\Outlook” folder. By default, Outlook creates a name for each e-mail account defined in the profile. The “Mail Account” is prefilled using your email address. If your email address is joe@gmail.com, and the Profile is called Gmail, then the file will be called “joe@gmail.com – Gmail.pst”. That pst file is Outlook’s shadow representation of the IMAP server’s folder structure. When you look in the Outlook profile’s Accounts Settings section, one of the files you see will be identified as the default mail address from which e-mail is sent. When using multiple accounts in a profile, any reply message uses the recipient e-mail address in the “From” field but you can change it using the dropdown arrow for the field in the “Reply” window.

Labels or is it folders in disguise?

Gmail uses “Labels” to create a file structure. In fact, the label is just a property attached to every e-mail message and the client , web or Outlook, uses it to organize and present messages. In the Google web client, the Account Setting determines which “Labels” will be shown in the web as well as in the Outlook client. Go to Settings and the “Labels” tab to make changes to the System labels or the labels that you create. You can then select whether to show or hide the label. Additionally, you can select the check box to show the label in the IMAP client program. Outlook then uses this information to create the folder structure you’re familiar with.

I select the Gmail Inbox, Sent Mail, Drafts, Spam and Trash system labels to appear in Outlook in addition to my user-defined labels. One thing I found confusing was the Google “All Mail” folder that’s available to appear in Outlook. It is in fact, all of the email that’s currently in your email account on the server. So in Outlook you can see the same message that’s in “All Mail” appear in the folder to which it’s assigned. Some find this helpful while I initially found it confusing. From a practical standpoint, you can choose to expose whatever system and user defined folders you want to see and hide “All Mail” so it will look like your traditional Outlook folder structure that’s created by default using POP3 or Exchange MAPI.

Calendar

As I mentioned previously, the “Outlook Data File” in My Documents is the local container for calendar appointments and contacts. You can synch up the local calendar with the Gmail calendar using the calendar synchronization tool. It’s available as a free download. Documentation as well as the link is located at http://www.google.com/support/calendar/bin/answer.py?hl=en&answer=89955. The tool provides one-way (Gmail to Outlook and Outlook to Gmail) as well as full, 2-way synchronization.

Contacts

Contacts are stored locally in the “Outlook Data File” in My Documents. You can import contacts from the web client to Outlook or from Outlook to the Gmail server. However; each method is on-way and requires you to export the contact list, preferably to a comma-separated file (CSV) or Text (txt) file and then import using that file. Unfortunately, to keep the list synchronized, you need to continually repeat the process using each client’s ability to handle duplicate records. This is clearly not a good solution.

On the other hand, Google provides a synchronization tool in Google Apps to accomplish this functionality. The tool is found at this address: https://tools.google.com/dlpage/gappssync. According to the documentation, the plug-in you use Microsoft Outlook as a client for Google Apps for Business and Google Apps for Education email, calendar, and contacts. Email, calendar events (including recurring meetings), and contacts are all synchronized between Google Apps and Microsoft Outlook. Google Apps for Business is presented as an alternative to Microsoft Exchange. Therefore, it is not an appropriate tool for an individual Gmail user.

Another Synchronization Solution

Another solution is worth pursuing that I found in the Google Forums: http://www.google.com/support/forum/p/gmail/thread?tid=40084927eec73635&hl=en. A popular post in the forum recommends Sync2, http://www.sync2.com/?pcode=803270342ci77. This solution allows you to sync Outlook data between computers using the Sync2 Internet service, a USB device or a network share. It also allows calendar and contact synchronization with the Gmail calendar and contact services. This solution is explored in another post.