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I have used PocketMac with an older Toshiba PocketPC:

Syncronization was spotty at best - in terms of "seeing" the Pocket PC - when it worked it worked fine, but it did not always work. I tried the troubleshooting tips suggested on their web pages, and a reinstall or two, but I'm not happy with the software.

Perhaps I'm spoiled - I can't think of any other software that I have on my Macs that does not "just work" - having to tweak and reconfig and uninstall and reinstall seems strange... I feel like I'm at work (I work in PC land... where ironically the syncing was seamless for me).

I'm going to order the Missing Sync shortly to replace my copy of PocketMac (though I have to admit that the theme that PocketMac gives you to load onto a pocket PC is quite nice).

If I remember correctly there were a couple of comparison reviews on the 'net. Check them out if you can. From what I remember they recommended the Mark/Space product, and my experience of PocketMac seems to support their conclusion. Maybe things would be different with a more recent handheld though - I was essentially trying to get an antique to talk to an antique.
 

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I have been using MissingSync to sync with my Pearl for a while now. The product is fairly solid. Definitely less problematic than syncing with a PocketPC.

Annoyance: MissingSync lumps all my calendar entries into one category under iCal, even as my entries are categorized into many headings under Outlook (which is also sync-ed with my work computer).
 

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Nothing but bad experiences with PocketMac - and I've tested on several different models of BB, taking considerable time to evaluate. Problems include constant duplication of addresses upon updating, runway processes, etc. Very frustrating and lame software.

Excellent experiences with Missing Sync. Everything works and in a fraction of the time. Fewer address and calendar platforms supported, but if you just want Apple Address book, iCal, and iPhoto etc its The Thing. Hands down.
 

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I've been trying out PocketMac with a Curve the last couple days, and it seems a tad strange. Sometimes it senses the Curve, other times it completely ignores it.

All my categories probably synched over to the device, but upon making a new calendar or task item on the device, it cannot seem to be assigned to a category, otherwise it gets lost in the sync. Also, after the third sync, all my calendar items were duplicated. After another sync, it seems to fix itself.

So PocketMac definitely has its quirks (but has improved since I used it last with a PocketPC device about a year ago). I'm going to try Missing Sync to compare, as I remember it being a much more solid program.
 
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