Having a BlackBerry is one thing, but keeping it organized and in sync with all the key information stored on your Mac is another thing altogether. We looked at two software applications, in particular, that are all about syncing your BlackBerry with your Mac.

The first is PocketMac for BlackBerry, a free downloadable app that allows you to sync everything from iCal calendars and tasks to your Address Book and email from Apple Mail or Microsoft Entourage 2004 and 2008, as well as Notes and Safari bookmarks. On top of that, you can also transfer music and photos directly from your

iTunes and iPhoto libraries.

The second is Missing Sync for BlackBerry developed by MarkSpace, which comes at a cost of $39.95 U.S. (though there is a free trial). This software essentially offers the same set of features, only with a very different interface and some extra advantages that PocketMac doesn’t have.

To run through these tests, I used a BlackBerry Bold and a black MacBook 2.14GHz Intel Core 2 Duo running on 3GB of RAM with OS X Leopard 10.5.6 with the latest software updates.

PocketMac

The first thing you’ll notice after starting up the PocketMac SyncManager is that you have the option of backing up your data through your MobileMe account. Curiously, PocketMac hasn’t updated the software to note the name change, as it’s still displayed under the old name of .Mac.

The rest of the interface separates the key syncing features into tabs. Click on any one of them and you see the menu options appear below. The Advanced Preferences buttons lead to a further set of criteria that you can set for syncing. For example, if I was only looking to sync over business contacts from Entourage 2008, I could just click that and it will only transfer those. If I want to overwrite my BlackBerry with the full contact list I have on Entourage, I could do that as well.

While this is all supposed to work properly in theory, the actual results go from mixed to downright frustrating. Syncing over the entire list of contacts actually works very well on the first attempt, but adding to the list afterward can be problematic. When I tried to update the list by adding a few new contact names, PocketMac wouldn’t let me sync over only the new entries. I had to sync over the whole list again. This is fine, but if I had separated contacts into different groups, PocketMac seemingly wouldn’t acknowledge them at all.

And in a strange twist, PocketMac doesn’t always transfer over multiple phone numbers for contacts. This bizarre issue was more than enough for me to make sure that I had my Address Book backed up. My worry was that in trying to overwrite my contacts on the BlackBerry, I might lose data on my Mac as well. I had read testimonials to this in some forums discussing PocketMac, but found none of my information was lost in the numerous attempts to sync over contacts.

Syncing email, whether it’s from Apple Mail or Entourage, is also a mixed bag. PocketMac offers an option to copy BlackBerry email directly over to Mail or Entourage, but it’s a little jittery in its performance. More often than not, it will work, but it made me wonder if the issue was with PocketMac not supporting the Bold as much as it would with a Curve, Pearl or some other model.

Email redelivery, which basically mirrors the email received on your Mac, worked well for me. It was a huge convenience to be able to respond to messages without going near my Mac. But the one problem that irked me was that attachments would sometimes show up only as text, or not at all in some cases. It can mistakenly make you think that the sender simply forgot to attach it, but unfortunately, PocketMac is a bit random when it comes to this.

I should note that PocketMac does offer syncing of contacts, tasks, notes and calendar from Lotus Notes and MeetingMaker, but without having to use them, I can’t definitively say whether or not they would work well.

A nice perk was the ability to sync over music from iTunes and photos from iPhoto. Moving over specific playlists or photo albums is as simple as choosing them from the list available, but expect it to take a while. The process is actually pretty easy, except that some songs I transferred hadn’t completed, so while the metadata was there, there was no actual music. I’m not entirely sure why this happened, since all the songs were in supported file formats, but in order to make it right, I had to overwrite the Bold and re-export the songs over.

It was unfortunate that I couldn’t sync over anything wirelessly with PocketMac. There’s no support for Bluetooth or Wi-Fi, as it only offers USB connectivity. Another oddity is that it displays Serial Port as an option (the plug older BlackBerrys use), but there’s a disclaimer upon installing PocketMac that confirms it doesn’t work in the first place. Why have it there if it doesn’t work at all?

And as nice as it was to have the option of syncing over bookmarks, only the ones from Safari will work. If you’re a Firefox user with tons of bookmarks, you’re out of luck. Your best bet is to find a way to move them over to Safari and then sync from there.

Missing Sync for BlackBerry

While it was easy to download and install my review copy of Missing Sync for BlackBerry, I did also have to make sure to install the mobile version onto the BlackBerry Bold I was using as well. MarkSpace offers instructions on how to do this, so it wasn’t a difficult process overall.

The first synchronization process with Missing Sync has to be done through USB, despite that Bluetooth is also supported. The interface is clean and fairly straightforward, with a little bit of customization thrown in. But it does require some digging to understand how it works. The Help section is a valuable resource for finding instructions on what to look for and how to get things working for you.

Missing Sync calls each sync option a “plugin” that requires checking the box next to it and then double-clicking on each one you want to sync. The window that opens up is a lot like a preferences pane where you determine what exactly you want to sync over to the BlackBerry, along with options to import data from the device as well. For example, I could export a couple of photo albums from iPhoto, while then importing images I took with the Bold.

I could also export my iCal calendar from as much as 18 months prior to 18 months into the future. Even the Folder Sync was a cool option. I created a folder with documents inside on my Mac and chose it to sync with a folder I had on the Bold. This meant that whenever I connected the Bold to the Mac for syncing, any new or deleted contents in that folder would replicate automatically. It works pretty well, but unfortunately, it can also get hijacked by some inconsistencies with other plugins. In cases where an overall sync isn’t successful, the Folder Sync may just not go through at all.

Generally speaking, syncing most things on Missing Sync seems to work well most of the time, but for whatever reason, iCal has some trouble migrating all the data successively. Though the sync may appear to have gone through perfectly, it seems miss some elements in the process. Syncing over Address Book does have some issues sometimes, but I found it generally worked well, especially since it included any and all phone numbers I had for each contact – something PocketMac failed to do.

Other options include backing up all text messages, which could be useful for those who need information from them. The rest is the usual mix of notes, contacts, tasks, music, video and even a log of all outgoing, incoming and missed calls. In particular, I liked that Missing Sync would keep iTunes playlists intact, which was a frustrating drawback with PocketMac. Rather than jumble all my songs together, all the playlists I synced over in my initial USB connection were right where I wanted them.

Pairing my MacBook with the Bold was relatively simple, but the Bluetooth connection kept stalling whenever I tried syncing. I tried re-importing my contacts, along with a small iTunes playlist of 10 songs. The contacts went through quickly, but the songs went through at an agonizingly slow pace. Worse yet, once only three songs went through, Missing Sync popped up an error message telling me that it couldn’t finish the job. Meanwhile, the Bold crashed and had to restart. I’m still not sure what happened, but I have to assume there’s some bug here that causes the problem because four more attempts gave me the same results. Still, even if it did work, the snail’s pace would’ve been unbearable anyway. A 7MB song was taking up to five minutes, so I can only imagine how long I would’ve waited with a 70MB video file.

It was nice to see that Missing Sync would actually convert video files so they could play on the BlackBerry, but needless to say, Bluetooth syncing is fine for quick and light data, whereas USB would be best for any of the heavy lifting with multimedia. The Proximity Sync feature connects the BlackBerry to the Mac via Bluetooth when it’s within range for automatic syncing. The good news is that you can utilize Proximity Sync to update the basics like your calendar, contacts, notes, tasks and text messages. But again, there are some issues that creep up. Errors pop up randomly, and in a few instances, the Bluetooth connection went down, even though my Bold was lying right next to my MacBook.

Final thoughts

Both PocketMac and Missing Sync can do the job but there are gaping holes in both cases. Neither of these is particularly adept in being consistently good at just syncing over information without some random problem creeping up. The real frustration isn’t in figuring out what the issues are, but in just getting it to work again without having to relaunch the application. This is especially true when trying to unmount the BlackBerry from the Mac after you’re done. Missing Sync offers an Eject button but it proved to be useless for me. PocketMac sometimes keeps running even after you’ve quit it. In my experience, I had to go to Activity Monitor just to finally close it.

As I’ve pointed out, these two apps have their share of issues, but it also depends on what you’re looking to sync over. I would point out that it might be easier to sync certain things as opposed to others, but there’s a certain unpredictability about how these two work that makes it hard to say.

For iTunes syncing, RIM is now offering its own BlackBerry Media Sync but the Mac version is still a preview build that could have its own issues. Ultimately, I get the sense that everyone’s experience with PocketMac or Missing Sync will vary somewhat. Some of the issues I’ve seen users point out on forums didn’t affect me at all, and vice versa.

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