Synchronizing Outlook on Two Computers


Friction Factor   =   NOW HIGH FRICTION


IMPORTANT UPDATE ON FEBRUARY 21, 2013 went out of business awhile back. One of the original developers is taking it over and changing it to a more sustainable subscription model. However, when coupled with the fact that confidential data will be passing through their server and the lack of track record, I cannot recommend this service now.

I have made the switch to using Google Apps along with Google Sync for Outlook. It is a terrific solution. Now my email (for all of my external, non-Google email accounts), contacts, and calendar stay in sync between Outlook, the Google cloud, and my smartphone. It is beautiful to behold and works perfectly. It took quite a bit of time to get it configured properly but that also highlighted an amazing level of customer service provided by Google. And I have documented what I had to do including several missteps that were corrected with technical help, so I can pass all of that along to you so it will be easier and faster for you. I am very pleased and now strongly recommend that Outlook syncing solution.


The Problem to Solve
I want to keep Outlook synced between my desktop and laptop computers. I sought a simple, elegant, transparent solution that just works and does not require Outlook to be manually closed on both computers before it can sync.

Seeking a Solution
Over the years I have tried many solutions, but kept ending up with a painful reality—having to manually close Outlook on both computers, then copy my PST from one to the other whenever I needed to use the laptop. This really limited using my laptop at home and made it a pain to prepare for travel. But I rely on Outlook so much that this was what I had to do.

Some people sync messages, contacts, and calendar by using an online service like Outlook Hotmail connector or the less-than-simple Microsoft Exchange solutions (if you use Exchange). Those are not good solutions for me. I have tried several third party products and services but have been disappointed in all of them until I discovered a couple of years ago.

Solution Found
Every few months I would Google search to see if a real solution had been made available yet. Finally I discovered As I reviewed the claims on its site, I became more and more excited but still wondered when the shoe was going to drop. It didn’t. Some things were not completely clear to me on their website, so I wrote to them and, lo!, they responded within a day, sometimes on the same day. So I got my license and installed on both computers (it runs as a background service). Setting up an “Outlook Group” for the computers was straightforward. Within minutes Outlook was successfully syncing in real-time between my two computers.

Whenever something changes in Outlook on one computer, it is immediately reflected in Outlook on the other computer—just as I dreamed it would work. I’ve always thought that I am surely not the only person on the planet who would benefit from such a solution. I was amazed first of all that Microsoft itself does not offer the right solution. But I am ever grateful to have discovered

I was nervous about my Outlook data being passed through a remote server. I was assured that the connection is secure and that it simply passes through; it is not stored on their computers except for the time needed to complete a synchronization. There is still a vague worry about my Outlook data passing through an outsider’s grasp, so there is a degree of trust one must hope will never be compromised by But the benefit gained is compelling.

I have been using for over a year and a half. It has brought a real, honest to goodness burden relief to my life. It just works. It doesn’t matter which computer I want to use at any given time. Outlook data is the same on both.

Not only does it work on my home network but, by virtue of it being an online service, real-time syncing continues automatically no matter where I am as long as I have an Internet connection to both computers.

Now my email, calendar, and contacts stay in sync automatically on both of my computers. Massive relief.

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It Does More also synchronizes selected folders between computers, but I already use Microsoft’s Live Mesh for this and am very happy with it. I also use Sync Toy when I want to do one-way synchronizations that are non-destructive at the destination. For example, if I accidentally delete a folder of family photographs on one computer, I sure don’t want to instantly lose my backup copy through a syncing action.

Editions offers at 30-day free trial. There are three “editions” – Personal, Business, and Manager. The personal edition includes licenses for three computers. As of the date of this article, pricing options and a features comparison table can be found at

Unlike most cloud-based services, this pricing is for a perpetual license. This is an amazing deal for their customers. If they change their mind and go to annual subscriptions, it won’t hurt my feelings. They are well worth it, and I want them to be in business for a long time to come.

Very Important Note
Don’t trust any software or service or yourself to not foul up. Before running, make sure you first make a copy of the active Outlook PST files on both computers. That way, if something messes up or if you delete the destination archive folder before discovering there was something else you wanted to save… you still have it in your backup files. I suggest that you regularly archive copies of your PST files anyway.


  1. If you have set up Outlook for timed receiving of your email, then you do not want to manually retrieve the same email on the other computer (we'll call it the secondary computer). Otherwise you’ll be inundated with duplicate emails as they sync from one computer to the other. In this case, set up Outlook on the secondary computer so that it does not receive email. To make this suggested change:
    • On your "secondary" computer, go into Outlook Options to Send/Receive Groups. In Outlook 2010 do this via File => Options => Advanced => Send/Receive.
    • Scroll down to the Send and Receive section and click the Send/Receive button.


    • Edit the Send/Receive groups on this computer to only Send email. Your "primary" computer will continue to receive email which will be synced to the secondary computer.
    • If the primary computer stops receiving and syncing email for any reason, you can still use Outlook's Send/Receive options in the main ribbon to manually request email from one or all of the accounts you have set up.
    • As you can see in the above image, I have created Send/Receive groups in my Outlook: All Accounts Send Only, will send my email when I press F9. I prefer that my email not be sent immediately...too many oops factors. Another group is for Timed Receive which I use on my primary computer to check for new emails every few minutes. This group is disabled on my secondary computer to avoid getting duplicates when gets the same emails from the primary computer. Similarly, the group Send and Receive All Accounts is disabled on my secondary computer. It is the one I use on my primary computer for F9 manual email processing.
  2. Keep your messages on the server for a short time. I have several POP3 email accounts set up in my Outlook. For each one, I have gone into Account Settings => More Settings => Advanced tab. There I check the delivery option to leave a copy of messages on the server for one day. Then, if syncing is down for any reason, I can always manually retrieve the day’s email on my laptop. The side effect is that when syncing comes back on, another copy of those messages will come in. Alternatively, I can check my messages via Web access to my mail account.

A Few Friction Factors
Low friction does not mean friction-free.

  1. If an import is aborted, the option to do the import goes away. How to get it back so the data does get imported into the other computer’s Outlook? You have to remove your syncing group, recreate the group, and start a new sync.
  2. does not yet sync folder changes; i.e., when you rename, move, or remove Outlook folders. That must still be done manually. This is frankly a pain.
  3. You can sync new folders. The process is not exactly intuitive but it is straightforward:
    • Right click the icon in the sys tray and open
    • Click “Details” for your Outlook Group.
    • Click the plus icon in the Outlook Folders section to open an “Add Outlook folders” window.
    • Check the box for the highest tree branch with “Automatically select subfolders” checked. You can scroll the list to see which new folders have been selected.
    • Click “Next” and “Next” again, then, after it completes packaging the new folders, click “Finished.”
    • You’ll see a notification on the other computer that an import is ready to be loaded.
  4. When initially syncing from one computer to another, the documentation is not clear on a couple of points. The computer selected to initiate the syncing matters. If Outlook is out of sync between the two computers, then create the “Outlook Group” from the computer that is most current. I always set it to back up the folders on the destination computer and create new folders to exactly match those on the source computer (note: for some reason, this is not the default setting). Select Folders

    Then I delete the backup folder created by on the destination computer.

    If there is any content on the destination computer that you want to preserve, then simply open the backup folder created by, drag folders or messages or other items to the "new" folders, then delete the backup folder.

  5. Infrequently the service is down for short periods (for maintenance I presume). This will, of course, normally happen as a Murphy strike…right when it’s inconvenient to happen. But it has been such a rare issue that I hesitate to even mention it.
  6. For some reason iCalendar messages do not sync. So when I get an invitation to a meeting, I don’t see it unless I am at my desktop computer. I’ve inquired with on this.
  7. The personal subscription is limited to 300 folders. How to know when you’re getting close to going over 300? I do not know of a way to get a folder count in Outlook. I upgraded to the business version and that limit has gone away.
  8. A rare possible inconvenience: You cannot move your license to another computer unless both are on the Internet.
  9. IMPORTANT: To back up your active pst file, Outlook cannot be running. And if is running, then the PST file is still locked even if you have closed Outlook. If you exit, the process is still running, so the PST file is still locked. To get around this you must:
    • open Task Manager by right-clicking the taskbar, and click Start Task Manager
    • click the Processes tab
    • find SyncingOLWatchService.exe and SyncService.exe
    • click each one to select it and then click the End Process button
    • close Task Manager and backup your Outlook PST file
    • restart Outlook which will automatically restart
  10. I wish when changing computers or reinstalling Windows, the process of resyncing would be easier.

If you use Outlook on two (or more) different computers and need to keep Outlook in sync on each of them, then I strongly recommend

Has the information in FrictionFactor been helpful to you?

Please take a moment now to support this effort with a donation. It is processed securely by Paypal. While any amount is appreciated, you might consider your cost or friction savings. Thank you!


Copyright 2013