jsnydcsa

I had been holding off on upgrading to Apple OS Mavericks (10.9.4) and the latest version of iTunes b/c off the loss of wired sync of Apple Contacts to iDevices. I really didn't want to be in a cloud sync solution and didn't have the wherewithal to set up a personal CardDAV system. So, I stuck with the older Apple OS and iTunes and continued with wired sync.

At the same time, ALL of my contact information was created/stored/updated in MS Outlook 2011 for Mac. And, via SyncServices (in MS Outlook), new contacts and changes to all contacts synced over to Apple's Contacts/Address Book program (for subsequent wired sync, per the previous paragraph).

Then, I recently read that Mavericks and iTunes had been updated to restore the wired sync functionality. Huzzah! Upgraded.

Now, I learn that Mavericks (or some aspect of the upgrade) no longer supports the syncing of contacts from Outlook to Apple's Contacts program. Argh!

I'd like to keep wired sync (but that's not "the problem"), but I'm S.O.L. on the Outlook---->Contacts sync. I really prefer Outlook to Apple's Contacts/Mail program and am loathe to maintain two address books (e.g. Truly "manual sync" by creating/updating contact in Outlook, then opening Contacts and create/update the corresponding contact there) as I'll never keep the two in sync.

Over at the Apple.com Support boards, I started looking at an Exchange hosted solution to load my Outlook Contacts up to Exchange then down to mutiple iDevices (three iPhones, four iPads). But, I'm truly concerned about the security of the data transferred to/from and stored in Exchange (hence my desire to keep wired sync). And, my initial attempts to set this up met with utter failure (nothing sync'ed, MS telephone help was useless).

So, what to do?
Anyone know of a workaround to continue the sync between Outlook and Apple Contacts?

Anyone know how to revert back from Mavericks and the newest version of iTunes (seems risky)?

Even assuming I could get it to work and overcome my outright obstinate refusal to load up 1000+ contacts (many with confidential info) into the cloud, how secure is Exchange?

Are the alternatives (more secure, less costly, better support) to Microsoft's own Exchange service - such as a web company that runs Exchange servers?

Notwithstanding going the Exchange route, my contacts will still never be "in" Apple Contacts, hence my interest in some sort of on-computer sync between Outlook and Contacts.

I really wish I had never upgraded! Perhaps in the future, MS would have upgraded Outlook to sync over to contacts and then I would have my Outlook--->Contacts--->iTunes Wired Sync--->iDevice sync functionality back. Until then, I'm forming the Coalition To Also List Downgrades with Each New Version of Software. Power to the Unupgraded! Protect the Second Adopters!

gfunkdave

I think Exchange is probably your best bet, but I know nothing about Apple contacts sync (I don't have a Mac). What are your particular security concerns? Everything is encrypted in transit and as long as you go with a reputable Exchange host you'll be fine.

Frankly, I'm not sure why you seem to trust Apple so much with your information if you're that worried about security. But take a step back too - why are contacts so secret? They're just contacts.

WIRunner

I had a customer a few years ago that needed a solution, we found that Syncing everything to Gmail and then to exchange was the only solution. Not sure if that is still an option at this point though.

javabytes

If the contacts are already in Outlook, it should be fairly trivial to set up an Exchange account, add it into Outlook on the Mac, and copy/import the contacts in. The contacts will sync with the Exchange server. Then add the account to the phone and pull the Contacts down. If you want Exchange, hard to beat Office 365 starting $4/user/month. There are other hosted Exchange providers, but in my experience they are generally more expensive, in addition to requiring a minimum number of users.

Should be able to accomplish the same thing through Gmail as well, if you don't want to pay for an account. Gmail supports contact synchronization via CardDAV. Set up your Gmail account, then export your contacts from Outlook and import to Gmail through the web interface.

jsnydcsa

Exchange does seem like the best bet. But, I can’t seem to get it to work and MS telephone help is not very … helpful. They seem to be heck-bent on talking about either (a) Outlook for Windows setup or (b) generally more sync’ing on email via exchange (which I don’t need) rather than contacts.

Is MS’s own $4.00 per month Exchange service encrypted? E.g. On the upload from my Outlook 2011 for Mac, on the Exchange server, and on the trip back down to a sync’ed device?

I have more than 1000 contacts (nearly 2000 actually) with lots of proprietary stuff in there about folks, companies, people I do business with. Plus, for some contacts - such as my bank - I have “reminders” about passwords, etc. The reminders would cue me as to what the password for an account is and would be likely complete gobbledygook to anyone else (e.g. “Pwd is mother’s sisters first dog’s name, plus last two digits of old NY apartment number, followed by second son’s initials all uppercase, plus @ and # sign”). I just don’t feel comfortable having this stuff stored in the cloud or on anything other than my own computer or on a backup/mirror copy on a portable hard drive that I secure on my own. I’d consider a lot of this information secret and not something I’d want taken in some data breach.

I don’t trust Apple with my info and am loathe to entrust MS or Exchange with it either. Right now (or at least until about a week ago) everything was kept on my machine in Outlook - which sync’ed over to Apple Contacts - which then synced to my iDevices via wired sync. No CardDAV, no servers, no iCloud, No WiFi Sync, No BlueTooth Sync. All on my machine and wired to the device during a sync via iTunes.

The $4.00 with MS is what I signed up for and it didn’t work and, as I mentioned, MS Support couldn’t help. See my comment to gfunkdave about MS Help.

That’s exactly what I want to do. But.
1) It still doesn’t help with getting the contacts sync’ed over from Outlook for Mac to Apple’s Contacts program on my Mac (rather than the iOS Contact Program on an iDevice). I’d REALLY like a solution that brought the sync-services based Contact sync’ing transfer back between Outlook and Apple Contacts.

2) Still convened about security.

3) Couldn’t get this to work and MS Help was of no assistance.

Thanks for any continued thoughts or suggestions.

gfunkdave

1. check what formats your Apple Contacts program accepts for importing/exporting contacts and report back to us.

2. What exactly are you concerned about? Whom are you worried will somehow read your password hints? Anything you upload will be encrypted in transport. If you're convinced that someone will somehow break into a data center and figure out how to zero in on your info of the millions of others there...then you've got bigger problems.


If all you want is to get your contacts into you Apple Contacts program, then all you can do is figure out its import/export functionality. And be sure to back up your contacts!

Google Contacts supports exporting to Apple Contacts, which apparently uses vCard format.

MareLuce

Asking someone who asked a privacy-related question why they should be concerned about privacy... makes my brain hurt.

I would never store my contacts on someone else's computer (i.e., "the Cloud") for the same reason why another person might not want to publish their contact list in the back page of the local newspaper, despite their newspaper's declining readership.

Separate from that, why give up your right to search and seizure by putting data that you create on someone else's computer (i.e., "the Cloud")?

Because you haven't done anything wrong?

LIH Prem

Which aspect of sync services is not being supported? From what I'm reading it says it is supported as long as you aren't using those initial versions of Mavericks. You said you are on 10.9.4, so that's not it.

http://support.apple.com/kb/HT5847

http://support.apple.com/kb/ts2481

jsnydcsa

Apple Contacts accepts vCards. But for some reason, the full contents of the information contained in the Outlook vCard format doesn’t translate over the Contact in Apple Contacts. Prior to the switch to Mavericks, this was not a problem, everything in the Outlook vCard moved seamlessly over to the corresponding Apple Contacts entry via sync services - no exporting/importing. Now, since the switch to Mavericks, sync services doesn't work (duh, why else is there this post), if I export/save an Outlook contact as a vCard and then attempt to import it into/open it in Apple Contacts, the contact is only partially imported.

I just don’t want the material stored offsite, in the cloud or what have you. Call it paranoia, call it whatever. Just don’t want it there.

If there was an ironclad way of knowing how to use Exchange to work and get the contacts “up” from MS Outlook for Mac and into Exchange and then “down” into the Apple Contacts program and/or my multiple iDevices, I might be willing to make the trade for security v. the gosh darned process actually working.

I’m so down the rabbit hole with MS, Apple help, chat boards, etc. I’m not going to open up another line of headaches via Google. Plus, Google doesn’t solve the security issue.



LIH Prem - Thanks. I pounded away at these KB articles for hours. They largely mirror a number of other non-Apple help sites about resetting sync services, deleting plist files, etc. Unfortunately, they didn’t work and I followed them to the letter as best as possible (some of the files they tell you to delete were simply not there).

I sense a few hours at an Apple Genius Bar in my future. This just sucks.

If I could ever get MS Outlook for Mac and Exchange to play nice and actually have my contacts sync "up" to Exchange. I wonder if I could sync them "down" to Apple Contacts as well as my iDevices. That might solve the mysterious loss of sync-services problem. But, it would cost me and it might not solve my problem in response to gfunkdave's point 1 above.