Syncing Issue

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Forgive me if this has been previously discussed. I tried the search function and couldn't find a thread related to my issue.

Every time I sync my iPhone 6 with iTunes it gives me the message you see in the image I attached (hopefully). It says syncing will change more than 25% of my contacts or groups on this computer.

I recently (finally) decided to stop using Microsoft Entourage for my office needs and use all Apple software like iCal, Address Book, and MacMail. I was able to successfully transfer my contacts and calendar appointments from Entourage to Address Book and iCal. So I remembered I still had that folder full of VCF's or whatever on my desktop from when I did the transfer and I thought that must be the problem. I deleted it but that didn't fix the issue. So then I went to the very laborious task of going through my contacts one by one with both my iPhone and my MacBook Address Book, making sure they all match perfectly. Of course there is the possibility going through that many contacts I made a few slip-ups, but 25%? Surely something else must be going on. Do I need to clear everything out of Entourage or completely delete the software? I'd like to keep it if possible even though I no longer plan to use it. As far as I know, I "disconnected" Entourage, but maybe I missed something and that's what's causing the issue?

Screen Shot 2015-01-21 at 8.46.40 AM.png
 

chscag

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Which version of OS X are you running on your MacBook Pro? Are you using iCloud to sync contacts? In other words, do you have iCloud drive setup on your iPhone 6 to sync contacts and whatever else you desire? And do you have iCloud setup on your MacBook Pro?

The VCF file you exported from Entourage - was that imported to your contacts app on the MacBook Pro? Also, you do not have to remove Entourage as that won't matter for syncing the contacts. Sorry about all the questions but we need to know exactly what you did and how you have your iPhone setup with your MacBook Pro with regard to syncing.
 
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Lefty Loco
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Hi chscag, and thanks a million for your willingness to help!

I'm running OS X 10.7.5

I am not currently using any iCloud services for anything other than "Find My iPhone," "Find my iPad," etc. Not quite ready to make that leap into the unknown and un-understood yet!

I followed this advice to make the transfer of contacts but now the link doesn't seem to be working Mac OS X 10.2 Address Book: How to Import Contacts from Entourage (I attached an image of the preview of that link, for what it's worth)

I probably did it in a very roundabout way, but I made a folder on my desktop and exported all contacts from Entourage to this folder as vCards. Then I just used the import function in Address Book to bring in this whole folder. As I mentioned, I subsequently deleted this folder, erroneously thinking that may have been the problem. This gained me a lot of duplicates, but I painstakingly I went through the iPhone and MacBook simultaneously to make sure they completely matched up. Also, I made sure to go into Preferences in Entourage and uncheck the sync options so it would stop muddying things up. Still no joy...

Screen Shot 2015-01-22 at 8.17.46 AM.png
 

chscag

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OK, thanks for the additional info. The best suggestion I have is to make sure you have a backup of the VCF file that has all your contacts and then go ahead and sync. If any contacts should get lost, at least you can go back.

I use iCloud and Yosemite for syncing my contacts. It's very easy to do as my contacts will almost immediately get synced to my iPhone and my wife's as I make changes in my contacts app on my Mac. Using iCloud is the way to go, but I can understand if you would rather stick with the way you're doing it.
 
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Lefty Loco
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Thanks again, chscag, for taking the time to try helping me with this. Unfortunately, I have previously tried just going ahead with the sync, which results in some duplicates and other annoying changes to my contacts list in the phone. Not only that, but it seems to happen every time! It's very similar to the problem where every time I sync, it has to transfer purchases that have already be transferred over and over again! I guess it may just be time for me to bite the bullet and go ahead and set up iCloud, despite my anxiety lol.

You said, "I use iCloud and Yosemite for syncing my contacts. It's very easy to do as my contacts will almost immediately get synced to my iPhone and my wife's as I make changes in my contacts app on my Mac." Do you know if this works both ways? In other words, if you change or add a contact on your iPhone, will it automatically sync via iCloud to the Mac? Most often I'm adding or changing contacts on my iPhone when I'm out and about.
 

chscag

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Do you know if this works both ways? In other words, if you change or add a contact on your iPhone, will it automatically sync via iCloud to the Mac? Most often I'm adding or changing contacts on my iPhone when I'm out and about.

Yes, it works both ways. It will not only sync back to my iMac but also to my wife's iPhone at the same time. I try to do all my contacts on the iMac because quite frankly at my age with old eyes, I hate typing on my iPhone. I forgot to mention to you that contacts, calendars, notes, etc, also sync at the same time to my iPad 3.
 
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Lefty Loco
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Hi chscag! I don't know if you'll see this or not, but if you do, I've finally turned on iCloud on my iPhone 6 and iPad and then turned on Mail, Contacts, Calendars, Reminders, and Notes. I'm about to activate it on my MacBook Pro as well but I have one last concern. Following the walkthrough on the Apple website, it says, "First, Update to the latest version of OS X. Is this absolutely necessary or do you think I'd be fine sticking with my OS X 10.7.5 (Lion)? I really don't want to make that leap as well as these all at once, for fear of something going wrong or becoming more complicated.
 

chscag

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Hi chscag! I don't know if you'll see this or not, but if you do, I've finally turned on iCloud on my iPhone 6 and iPad and then turned on Mail, Contacts, Calendars, Reminders, and Notes. I'm about to activate it on my MacBook Pro as well but I have one last concern. Following the walkthrough on the Apple website, it says, "First, Update to the latest version of OS X. Is this absolutely necessary or do you think I'd be fine sticking with my OS X 10.7.5 (Lion)? I really don't want to make that leap as well as these all at once, for fear of something going wrong or becoming more complicated.

According to Apple, you should be able to stick with Lion and not have to upgrade if you don't want to. As a matter of fact, Lion is the minimum version of OS X that you can use iCloud with. However, you really should consider running the latest versions of iOS and OS X if you can. It's understandable to be apprehensive and not wanting to mess with things when they're running well. But, eventually you will fall behind and reach a point where you can no longer run some of your favorite programs. Besides, there is always the security aspect as Apple drops support for Lion. (Which they will do.)
 

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