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15 Reader Question: Synchronizing Microsoft Outlook inboxes

A reader with multiple email accounts and two different computers (both with Microsoft Outlook 2010) has a problem that anyone who occasionally does the “work from home” thing can probably relate to: he wants to receive all his emails on both computers. But how?

I have a laptop at home and a desktop in the office. Both these computers use Windows 7 and Microsoft Office 2010. … On a daily basis, I receive emails with attachments up to 20 MB in size.

… I am having difficulties in maintaining an up-to-date  status on both the above mentioned computers when moving between office and home and vice-versa.

Presently, I am depending on Outlook’s Import and Export feature to export mails to a portable hard disk before leaving office. When back at home, I export this data from the portable hard disk to my laptop. The next morning, I export from the laptop to the hard disk. On reaching office, I have to import from the hard disk to the desktop. Also, it takes 10 minutes for each export or import.

Needless to mention, the frustration that I will encounter, if someday I forget to export or import.

I am sure you will have a workaround for such a tedious problem and anticipate your guidance.

‘Indeed I do,’ I thought to myself. (And, yes, I think “tedious” is the perfect word to describe the export/import routine he’s shackled to!)

For years, I’ve had a similar problem — namely, needing to access my most recent messages via webmail and/or smartphone during the day while Outlook is periodically downloading messages on my main PC. But I’ve solved it through the years with one simple setting in Outlook.

Many Outlook users don’t know there is a setting available in each email account that instructs Outlook to leave new emails on the server for X days (you specify how many days). To change that setting on each Outlook 2010 computer, go to the File tab and click the Account Settings button. (In Outlook 2007, you’ll need to go to Tools | Account Settings; click here for instructions on 2003 and earlier versions.) You’ll see a list of all of the email accounts you’ve set up.

(And, yes, I have way too many email accounts.)

For each email account, click on the name of the account (click #1 above), then click Change … (click #2) to get to the Internet E-mail Settings dialog box. Once there, go to the Advanced tab:

Once I’d outlined that setup, I thought it was “problem solved” for my reader. No such luck. As it turns out, Outlook automagically (yes, I know that’s not a word) marks messages on the server to remind itself, “yes, I’ve already downloaded that,” which means the second installation of Outlook won’t download it whenever that one does Send/Receive.

So, I went back to the drawing board. After doing a little research, I came across an article on Outlookipedia that listed a number of applications that purport to synchronize your Outlook setup between, say, your desktop and your laptop (as in this reader’s case). Here’s an excerpt:

How do you sync Outlook between two or computers?

While there are many useful utilities and addins offered by Microsoft that are designed to help you better manage Outlook; Microsoft does not offer a built-in feature or addin that allows you to keep Outlook synchronized between two or more different computers. However, the demand for a utility to sync Outlook between two or more computers is so great that there are quite a few addins offered by 3rd party software developers that actually do this quite well.

It should also be mentioned that there are several manual methods that you could employee to synchronize Outlook between two or more computer, but they appear to be quite time consuming and error prone and thus we will not waste your time in mentioning them. As previously mentioned there are quite a few addins offered by 3rd party developers that automate this task for you.

(Excerpted from Synchronize Outlook between two computers on Outlookipedia)

Just reading through the list of applications and their descriptions, there’s quite a bit of variance in what they synchronize (email only, email and contacts, the entire .pst file, etc.) and how much manual intervention is involved (i.e., whether you have to initiate the synchronization on either end and what equipment is involved). For my part, I’m inclined to go with something that synchronizes automatically over the Internet, but that comes with its own security risks that only the individual user can weigh for him/herself.

Unfortunately, I can’t really test this myself, but our intrepid reader is going to download one or more of the third-party applications listed in this linked article and let me know in a couple of weeks or so how he fares. Stay tuned for an update or, if this is a problem you’re having, try one of these yourself and let me know what you think!

Got a question of your own? Ask it via my Ask the Guru page!

Edit: Read the follow-up to this post (with the results of this reader’s testing) here.