Keeping a Pocket PC, Outlook, Mac iCal, and a Palm in Sync

This post is for all the people who try to keep the data on a number of devices in sync. This is a November 2007 update to an original March 2007 post, and is intended for people with multiple devices and/or those who use both Windows and Mac.

My own situation is that I use an iMac, Windows, a Pocket PC (Dell x51v), a BlackBerry Curve, and sometimes a Palm TX. There is no real reason for me to keep three handheld devices, but I do have them, and ideally would like to keep them all in sync.

There are several approaches you can take regarding syncing your data across multiple platforms:

• You can use a hosted exchange service with a suitable PDA (Smartphone, BlackBerry, a Pocket PC with Wireless connectivity), Outlook, and Entourage on the Mac.
• You can use an online syncing service that is designed to sync across multiple platforms. You can get a sense of one such service, Plaxo, by reading A Look at Plaxo: My Interview With Plaxo VP John McCrea
• You can use software on your Mac to brute-force a syncing between iCal, Address Book, Outlook, and a Pocket PC. I describe how to this below, in the section entitled “Using Missing Sync.”
• You can say screw it all, and just keep your data on one platform and one handheld device. In my case, I run Windows on my iMac through VMware Fusion, so I can have Windows and my iMac operating simultaneously and can even copy and paste data between them. I describe this a bit in How VMware Fusion Eliminates Some of My Syncing Woes
• You can also say screw it all and just use online tools such as Google Calendar, Gmail, and Remember The Milk.

I have talked with several business professionals who have spent countless hours trying to sync data across multiple platforms and devices, and they are increasingly leaning toward the latter two of the above options. (I personally use the VMware Fusion solution, although I am leaning toward the online data approach as well.) At some point you have to remind yourself that the objective is that the technology serve you, not the other way around.

I discuss some advantages and disadvantages of each approach in below. I hope you will share your insights on this issue in the comments. There is probably much we can all learn from each other in this area.

Using a Hosted Exchange

My friend Thomas Hall swears by this approach. I used it before I retired, but that was also before I bought my iMac. I did recently try it, setting it up first in Outlook via the Windows partition on my Mac, and then setting it up on Entourage on my iMac. When I got to the part of setting it up on my BlackBerry Curve, I found out that I need to have BES (BlackBerry Enterprise Service) instead of the BIS setup I have (BlackBerry Internet Service). Given that this could cost me up to $30/month extra, and given that the hosted exchange cost is about another $20/month, I decided against this path.

If I were working full time and on the road a lot, hosted exchange service might appeal to me. But, for a retired guy like me, who travels very little and has pretty much a fixed income, it made no sense. This is a great option for you to look into, though, if the cost does not concern you and if you use Entourage on a Mac (hosted exchange does not work with iCal).

One other thing to be mindful of with this approach: it does not work with an iPhone. This is another of the reasons I have decided to not use hosted exchange. It may be several more months before I get an iPhone, but at some point I would like to and would like to make it my primary device. Correction: Turns out you can get an iPhone to work with hosted exchange. You first use hosted exchange to sync with Entourage on the Mac and then use iSync to sync that to iCal and Address Book, which of course you can sync with an iPhone.

Using Plaxo

For a while, I thought Plaxo was a good solution to my efforts to keep two platforms and several devices in sync. I can say that it does a very good job of syncing what it does sync. The only real downside I saw to it was that it does not sync your Outlook Tasks to iCal (or vice versa). And, it creates a new calendar in iCal that has all of your Outlook entries in it, rather than creating separate iCal calendars for each Outlook Appointment Category (such as Work, Home, Travel, …). If you want true syncing across Outlook and iCal, it does not really give it to you.

Plaxo does have the added benefit of syncing your data to Google Calendar. It also does a great job syncing contact information. If you are an appointment-focused and contact-focused person, and not a task-focused one, Plaxo could be a good solution for you: the only problem I have with it is in the Tasks area. Clarification Update: Plaxo does have an online Tasks application, which contains the Tasks synced from Outlook. It is possible to use this and just forget about Task syncing with iCal.

Using VMware Fusion

VMware Fusion lets you just ignore iCal and Address Book in the Mac, so that you use Outlook exclusively, even though you are at your Mac. The only downside I am aware of for this approach is that it does not populate your Outlook data into the Mac apps, so if you want to do that, this does not get you there. If you decide you don’t care that the data is in iCal as long as you can access it in Outlook from your Mac, this is a painless way to go. It is the approach I currently use.

Using Online Data Services

A lot of people I know are just fed up with trying to keep data on different systems, and are using Google Calendar and Remember The Milk and Gmail and similar apps for just keeping their data online. If you can be connected all of the time, this is probably the most sensible approach. Software manufacturers will always stick with their own data formats, and there is virtually no hope that iCal and Outlook and any other PIM software will ever use a common format that makes it easy for you to sync your data between them. Going to an online approach overcomes this problem.

Note, some online PIM applications are compatible with Google Gears (for example, Remember The Milk is), so you can have your data without even being online.

A final thought on this approach: it should work well with the iPhone (or even with the iPod Touch, if you decide to use it is a PDA).

Using Missing Mac on the Mac

After first getting my iMac, the approach I first took to syncing my existing Outlook and Pocket PC data to it was to use the sync tool Missing Sync. This software is available to sync Pocket PCs (and Smartphones), Palms, and BlackBerrys to Mac computers. At the time of this update (November 2007), it does not fully support the Leopard operating system, although there are beta versions of it for Leopard. (When I upgraded to Leopard, I did not install Missing Sync, because I had learned that it is difficult to do a complete uninstall of it if you decide you do not want it. However, the software does operate very well, at least I had good experiences with it overall on my Tiger operating system.)

Using this software can work pretty well. Also, it is generally straightforward to use, so I won’t go into a lot of detail on it. I do think it is important to point out a couple of areas that can be problematic, though. I do go into a good bit of detail on these, just in case you run across the problems when you use Missing Sync. A final point before getting into using Missing Sync: there is a recently-released alternative called SyncMate, which is available in for download here. I have not tried it but thought you should be aware of it. It is free while it is in the beta stage … I do not know if the developers will ultimately charge for it or not.

When I used Missing Sync to sync the Outlook data from my laptop’s Outlook and my Pocket PC, I don’t think I had any problems. I honestly do not recall at this point. (Getting old sucks.) But, when I used it to sync with the Windows partition on my iMac, which I had set up using Apple’s Bootcamp, I had problems with duplicate entries. After considerable experimentation, I finally figured out the probable cause of the duplicates: the system clock on my BootCamp Partition was not in sync with the one on my Mac’s main partition. In fact, the clock in the BootCamp Partition (Windows) was off by several hours.

It is crucial when syncing between multiple systems for the clocks to at least be close to the same time. Does not have to be exact, of course, but when two systems are off by several hours you can really get into some problems. (I no longer have this problem. I don’t know if the later versions of BootCamp fixed it or if VMware Fusion forces a clock sync, or what.) This is also something to keep in mind when making time zone changes (including the periodic shuffling some countries do with Daylight Savings Time).

But, before I identified the clock difference as the likely culprit, I found some ways to brute-force a synchronization between the iMac, the Windows Partition, and my Pocket PC. The remainder of this article describes how I did that. If you are not yet proficient with Outlook, it may be worth the read just to find out some of the tricks I used on Outlook.

The first thing I did was to back up all of my Calendar entries (which is where the bulk of the problems were taking place) by creating a new folder within Outlook. I did this by selecting View within Outlook and then selecting Folder List within it:

Then, I created a new calendar by right-clicking on the Personal Folders folder and selecting new folder, with the result the following poping up:

Note that Outlook defaults to creating new folders that are designed for viewing “Mail and Post Items.” So, I instead selected the new folder to contain “Calendar Items.”

Once this was done, I created a view within my Calendars that would enable to see all of the Calendar entries in list form, along with a time-stamp showing when each entry was modified. The reason for using this time stamp is that enabled me to see, for duplicate items, which had been the most recently created one. A bit more on this part later.

I created this new view by selecting View from the Outlook menu, then Arrange By, and then Current View, as shown below:

Then from Current View, I selected Define Views, and you can see from the following which fields I chose to have included in the Calendar view:

Note that Outlook defaults to showing only Frequently-used fields, which does not include the Modified field, so I selected the option to show date and time fields so I could include the Modified time stamp.

Once done with all of this, I viewed each of my Calendar items, deleting duplicates as I went. (Where there was a duplicate, I deleted the older of the two entries, meaning that I was keeping the entries that had been synced with iCal.) Then, I copied all of the calendar entries to the CalBackup folder that I had created earlier.

Then, after I was content that my Outlook Calendar and Task entries were all okay, I booted back into the Mac operating system. I made sure that the system clock was not out of whack, went through the iCal entries and deleted any that were dupes, created a backup of iCal (just in case), and then used Missing Sync, again, to sync my Pocket PC to Outlook.

I do not recall how many iterations I had to go through to get everything in shape. I think it was a couple. It might have been a few. It should have been only once, but, regardless, it works now and indeed works just fine.

If you’ve had similar problems with multiple-device syncing, let us hear from you.

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