POP3 – Outlook Calendar Sync

This is a companion piece to the gMail – Outlook 2010 Calendar Sync post where I discussed calendar synchronization between Outlook 2010 and the Gmail Calendar. This piece will focus on Hotmail’s Outlook 2010 Synchronization tool called the Hotmail Outlook Connector.

The Since Microsoft owns Outlook as part of Office 2010 and Hotmail, and because integration with desktop Office and cloud-based Office Apps are central to their strategy, Microsoft took a more holistic approach to integrating email functionality. With Microsoft Outlook Hotmail Connector (32-bit or 64-bit), you can use Microsoft Office Outlook 2003, Microsoft Office Outlook 2007 or Microsoft Office Outlook 2010 to access and manage your Microsoft Windows Live Hotmail or Microsoft Office Live Mail accounts. This functionality includes e-mail messages, contacts and calendars.

Hotmail is free and it’s POP3. POP3 mail introduces you to the dreaded synchronization problem that you encounter using multiple computers to access your email. In a nutshell, POP3 email is a stroll down to the mailbox at the curb to download your mail to your computer.

Let’s take the steps in order: email arrives at the postoffice (hotmail.com, live.com, msn.com). The postoffice delivers the mail to your mailbox. Your Outlook program reaches out to your mailbox and delivers your mail to your computer. So what’s the problem with that, you say? Well, the messages are no longer at the postoffice, or the mailbox. They are on your computer. Suppose you have multiple computers running Outlook: at work, a netbook, laptop, iPad or a mobile device. If each of those uses an email client using POP3 protocol to get mail from your mailbox, then all of the messages that are in your mailbox will be delivered to that device when it connects.

This behavior is the default setting when using Outlook and may be the same for the other email programs used on other platforms. Of course, the problem is that once mail is delivered in Outlook, it is no longer on the server and doesn’t show up again in Outlook running on a different computer.

To over come this behavior, use the the Advanced Settings tab to check the box that leaves email on the server for a number of days before automatic deletion occurs. Then within that time period, when you connect to your mailbox, Outlook will perform a very simple synchronization and only download mail in your mailbox on the server and not in Outlook. Collectively, the other Microsoft email domains, hotmail.com, live.com, etc. are referred to as Windows Live. Windows Live offers Contacts and a Calendar.

Contacts are very important because they are used in Messenger, photo sharing, SkyDrive and other Social Media offerings, part of Windows Live. Contacts have a Windows Live email address and that email address is your WindowsLive ID, otherwise known as a Passport ID. Now, all of your friends don’t have a Windows Live ID, Most don’t but in order to make their Social Media offering work, they needed a place to store the Windows Live credential. Might as well be Contacts.

To keep these three objects synchronized, download the tool from  http://www.microsoft.com/download/en/details.aspx?id=24677. You’ll find installation innstructions and a link to the 64-bit version of the program as well. The connector runs as a Windows process, HOTSYNC.exe and starts automatically.  When you add a Windows Live email account to your Outlook profile, the account appears as a folder in the email navigation pane located on the left-hand side of the Outlook window. Likewise, the Contacts and Calendar belonging to the Windows Live account show up in the respective Contacts and Calendar section. 

You can expand the account folders in the section to view as much detail as you want. The entries are not merged in any way. This is pretty slick and in some ways is better than the GMail behaviour. Also, you don’t have to export and import Contacts to keep them synchronized. When you click the Outlook Send/Receive button all entities are updated.

Remember the connector works with Windows Live accounts in Outlook, so your primary email account may be on an Exchange server or you can use IMAP to connect to Gmail. The Hotmail Outlook Connector doesn’t interfere with the Gmail Calendar Sync tool. Gmail will sync to the native Calendar in the Outlook profile.

Other email service providers offering a web calendar, provide a synchronization tool. So far I haven’t found any thing interfering with another’s operation. Very well-behaved applications, indeed!