I’m on a Blackberry Curve right now and I’d like to move to an Android-based phone. Since Android plays so nicely with Google apps (calendar, contacts, etc.) and as I’d like to have everything in a nice central location, I figured I needed to get my info Googlefied.

I need keep the following in sync:

• Outlook: My current system of record. Meetings get scheduled here, I do most of my daily work here.
• Blackberry Curve: My phone (for now).
• Google: A centrally accessible place, plus my interface with the Android phone I want to get (not sure on model yet).

For the Blackberry, the Blackberry Desktop Manager software works fine to sync. It’s not awesome - actually, it feels very fragile - but it mostly works. For the calendar, there are some odd issues with recurring appointments, reminders, and meeting attendees that I’m not thrilled with, but no showstoppers. Contacts appear to sync perfectly.

That leaves getting Outlook synchronized with Google, which is not an uncommon problem.

Failure 1:Plaxo

I’ve had a Plaxo account for a long time and a year or two back I upgraded to the premium account because I had some Outlook profile issues that caused all of my contacts to be lost. Having the automated remote backup for contacts was a lifesaver and still gives me peace of mind.

Plaxo has the ability to synchronize with various places, which is cool. Unfortunately, Google used to be one of those places but is not anymore. Calendar sync was working great until a couple of months ago, but contact sync never worked. Odd since Plaxo is a contact-based product. Research in the forums tells me they’re aware of the issue but there’s no schedule for a fix.

Failure 2:SyncMyCal

SyncMyCal came recommended to me by a couple of different friends who have been using it successfully, though I’m not sure how. I didn’t find any problems during my trial period, so I purchased… and then instantly found four problems.

• Some Outlook contact fields don’t sync right. I couldn’t figure out exactly what the pattern here was, but I noticed that some of my contacts were not synchronizing. SyncMyCal tries to synchronize some Outlook contact fields as “user defined fields” in Google (because Outlook has so many fields on a contact) but sometimes it only sends over the field value and forgets to send a key. In Google, each custom contact field has to be a key/value pair. You end up getting a Google API error if you don’t do it right… and SyncMyCal doesn’t always do it right.
• Reminder information isn’t synchronized if you don’t set up your Google calendar with a default reminder. In order for meeting reminder information to be synchronized to Google, you have to go into your Google calendar settings and configure a default reminder value. If you don’t, none of the appointments that get synchronized will have the reminders attached. This was a hard one to figure out, but at least there’s a workaround.
• Contacts with multiple mailing addresses don’t synchronize all addresses. Say you have a contact with a work address and a home address. SyncMyCal picks one (apparently arbitrarily) and that’s the one that gets synchronized with Google. The other address(es) don’t get synchronized or even acknowledged. (Multiple email addresses synchronize fine; it’s multiple physical mailing addresses that have problems.)
• Recurrence exceptions don’t synchronize from Google to Outlook correctly. Set up a recurring appointment in Google that runs every weekday for two weeks. On the second week, delete the Tuesday and Thursday appointments. Move the Wednesday appointment to one hour later. Now sync back to Outlook - SyncMyCal will still show the deleted appointments and the moved appointment will still be in its original slot. It doesn’t properly bring those exceptions back from Google. (It does, however, send exceptions properly from Outlook to Google.)

Finally, support for SyncMyCal is horrendous. You file a ticket, you get back a copy/paste response about how they’re sorry for the inconvenience… but no real solution. A month later, they’ll send you a patch for the old version of their product and give you a bunch of steps to run through involving backing up your data, uninstalling/reinstalling SyncMyCal, etc. When you finally do it, the patch they send won’t even communicate with Google, let alone synchronize. You report that, rinse and repeat. It’s like they didn’t actually try any of the patches they’re sending you.

Why are they sending me patches for the old version of the product? That doesn’t even make sense. I asked about that, too, and got an unclear answer about design problems or something.

Anyway, I reported all of these issues over four months ago and have had no resolution on any of them. I can’t really turn on two-way synchronization if neither calendar nor contact sync actually works. There goes $25.

Failure 3:Google Calendar Sync

Google Calendar Sync wasn’t that bad, but I found that it didn’t actually sync all of my meetings properly. I couldn’t ascertain the pattern here, either, except that it would sync appointments (no attendees) and some meetings… just not all meetings. I’d get an error in my synchronization log saying “Participant is neither attendee  nor organizer.”

There are tons of forum posts about this with just as many different things that “fixed it” for people. I tried all of the fixes people recommended and none of them got all of my meetings synchronizing. (Though, interestingly enough, two-way sync didn’t delete the meetings, either. They just sort of got ignored.)

Success:gSyncit

gSyncit does calendar and contact sync… but also task and memo sync, too, which is more than the above products do. I’ve been running two-way sync on the calendar, tasks, and memos now for a couple of weeks and it correctly synchronizes everything - recurrence exceptions, reminders, everything.

The only problems I’ve had with calendar sync involve really crazy recurrence exceptions and time zones.

I’ve caught it a couple of times where I was messing around and created a recurrence exception on Google, synchronized to Outlook, updated it in Google, and it didn’t properly update back to Outlook… but I was intentionally testing the boundaries so I probably did something really edge case there. (Just be aware, is all.) I tried to set up a specific reproduction but haven’t figured out quite the exact set of steps.

Also, I’ve had a couple of weird issues involving time zones - like if a meeting organizer sets something up at 12:15 EST, that’s 9:15 PST… but somehow it gets interpreted as 9:15 EST - the local time, the remote time zone - and ends up appearing at the wrong local time (in this example, 6:15 PST). It’s only happened for two meetings (neither of which I was going to anyway…). I reported it this morning and got an answer from support within 15 minutes. (The SLA is 24 - 48 hours, but I won’t complain about a 15 minute turnaround!) This is apparently an issue with Google Calendar not handling time zone issues well. The author is working on a fix that may resolve the issue.

I have not yet run contact sync two-way, but one-way from Outlook to Google works perfectly. It caught the multiple mailing addresses without issue, correctly located the contacts I already had in Google and added to their profiles… just fine. Honestly, the only reason I haven’t done two-way sync is because I have to clean up my contacts in Google a bit - I’m afraid I’m going to get a ton of junk flooding into Outlook that I don’t want. I have full faith that the two-way sync will work fine.

UPDATE 5/25/2010 12:00P: I enabled two-way contact sync between Outlook and Google “My Contacts” folder after doing some cleanup and it worked very well. It did add some contacts to Outlook that were in my Google “My Contacts” group that I didn’t want, but after I moved them out of “My Contacts” into “All Contacts,” they were properly removed from Outlook. I also had a couple of duplicates appear where in Outlook I had one email address for a person and in Google I had a different address. A little manual merge action fixed that up without issue and now I’m two-way-syncing my way to freedom and leisure.

It’s pretty flexible - you can sync multiple Outlook calendars to Google calendars (and you choose the mappings). You can sync your contacts with specific groups (e.g., the “My Contacts” group in Google rather than the “All Contacts” group). Memos get synchronized as Google docs and you can put them in a specific GDocs folder to keep them separate.

The only weird thing is that tasks synchronize with a separate calendar and show up as events. The reason is, apparently, that there’s no Google API to interface with the actual task list. I’m OK with that.

Downside: You can’t really tell at a glance when the last time you synchronized was or the number of items synchronized. The best you can do is look at the debug/error log, but it’s not straightforward.

Anyway, if you’re looking for sync software, check out gSyncit. I really like it, and for $15 (at the time of this writing), you can’t really beat it.