Best way to start syncing iPhone contacts with pictures to Google account?

I already use NuevaSync [free] for my Google Calendars. It does what I need nicely.

I'd like to start syncing my contacts as well. Right now I have all my contacts in my iPhone (500+), most of which have pictures. I can sync to my OSX 10.5.7 computer and easily backup all the contacts to a big VCF file, including the pictures (they get encoded in base64 inside the vcard entries).

What's the NuevaSync approved method for getting OTA sync going between iPhone <-> Google, taking care to make sure the exact settings on my iPhone, like contact pictures, are preserved? I'm happy to wipe out my Google contacts completely, same with my computer, since I have a backup in vCard format and can restore at any time.

The recommended method is to upload that data to Google. I'm not 100% sure if this will preserve pictures though. It should, but I haven't tried it myself. You can also try the native iTunes iPhone->Google contacts sync method (tethered). Run that once and the result should be an uploaded copy of your existing contacts.

Actually I've done both of the following methods and can verify they don't preserve pictures:

(1) iPhone -> OSX Address Book (pics are still there) -> a single big vCard v3.0 XML file (pics are still there in base64 encoded format) -> Google Contacts "import form vCard" (this dropx all picture information)

(2) iPhone -> OSX Address Book (pics are still there) -> Address Book sync to Google Account (this drops all pictures when it hits Google).

Someone mentioned the Google API for Contacts to me and I see it has a special section about how to upload photos via HTTP PUTs, unfortunately unless I can write a script I don't see a way to utilize this and I can deduce that Address Book.app doesn't use this method. http://code.google.com/apis/contacts/docs/2.0/developers_guide_protocol.html#photo_management

I also see a competitor of yours, Spanning Sync, specifically mentions they can do what I need with pictures http://www.google.com/enterprise/marketplace/viewListing?productListingId=3524676+1804610058717551366 (search around in their features for confirmation). I'm not saying I'd rather use them, since they don't have a free option, I'm just pointing out that I know it is possible so I hope to eventually fine a long-term solution.

Can anyone confirm that contacts, once I've got NuevaSync <-> iPhone syncing via Exchange, who get a new picture assigned will get pushed to Google? I only set pictures for contacts via my iPhone, not through Google (at least for now).

Hmm...I was thinking of the 'direct to Google' contact sync in iTunes (which doesn't go via the desktop address book). I think this feature is in the Mac iTunes. But I don't know if it does pictures anyway.

Spanning Sync does Mac desktop apps to Google sync, and it's a product that many of our users use for that purpose.

Pictures added to contacts on the iPhone do sync via our service to Google.

This message was edited 1 time. Last update was at 15 Jul 2009 20:48 PDT

Ah... I didn't know iTunes had that sync built right in. I see http://support.apple.com/kb/HT1245 describes how to use it, and sneakily enough I see the "sync to google" is already checked in my case, which implies iTunes is simply harnessing the Address Book.app connector (which I left Google checked for a few minutes ago).

Trying now...
EDIT:
... using iTunes directly has the same failure as using Address Book.app, unfortunately.

I posted a question about syncing contacts' pictures via Plaxo elsewhere on forum, but didn't get a response. So, I will try to insert it in this thread.

What's the current deal with syncing contacts' pictures (assigned on the iPhone) to Plaxo? From this thread I gather syncing with Google Contacts is a nice two-way, seamless affair. But it seems not so with Plaxo contacts?

I don't see any sync happening and every time I have to reset my NuevaSync account on the phone, I have to re-assign contact pictures again.