iCloud and Outlook 2007 iCloud - Initial setup with live data on all machines

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Outlook version
Outlook 2021 64 bit
Email Account
So, I got mine working and syncing fine:

Windows 7-64 , iTunes 11.x, iCloud Control Panel v2.1.2

Outlook 2007


iPad2 - iOS v6.1.3

Now, I want to get my wife's set of machines working:

Windows 7-64 (a different machine) , iTunes 11.x

Outlook 2007

iPhone-3gs - iOS v5.x

iPad2 - iOS v6.1.3

The difference is my iPhone-5 was brand new with no contacts (my iPad2 was also empty). On her's, she has unique Contacts in phone and Outlook ... and hasn't synced by USB cable in a long time. What's going to happen? Many of the Outlook records have the email address, but the phone has the phone numbers (and likely slightly different name spellings). Which set of contacts takes precedence, or do they get merged together (dups but no loss)?

Her Outlook file is also pretty messy. Once, a couple of years ago ... we synced her iPhone to Outlook the old (iTunes only) way via USB cable. It sync-ed all contacts in both directions. We didn't lose anything but were left with a mess. Needless to say, she never cleaned it up. However, now that see sees how nice my set of machines work ... she wants the same. Will also help when connecting her phone to car or when she gets her new iPhone-5 or 5s.

I was thinking I might do the steps this way:

- Clean up her current Outlook file manually (combine all person's data into one record).

- With phone in one hand, go through each Contact on phone display and check/enter-it in Outlook 2007

- Setup iCloud-CP and let Outlook over-write what's on phone with the good Outlook contact database

But I forget if "over-write" or "keep only what's in Outlook" is even and option. It would be a shame to do all that work and have the phone records mess it up on sync. I will backup her .PST for that safety net, but I wonder ...

... What would you guys do? Anyone ever done this before?

If it only merges ... maybe I should iCloud Sync first (create even more of a mess) but THEN start cleaning it up. At least this way, after cleaning I'll be done.
Re: iCloud and Outlook 2007 iCloud - Initial setup with live data on all machi

I don't think iCloud gives you the option to overwrite, it merges.

I would definitely clean up the contacts folder before doing anything. Once clean, move to a new folder - you do not want these contacts synced yet.

Set up iCloud and sync. Clean up the contacts in the iCloud folder in outlook then compare/merge the original outlook contacts.
Well, she never cleaned-up her Outlook Contacts. However, we got her a new iPhone-5s. So this is what I did ...

Before going to AT&T Store (to get the new iPhone-5s), I backed up the iPhone-3gs to iCloud. When we activated and did First-Time-Setup on iPhone-5s, we "Restored from iCloud" (using only iPhone). This worked nicely and got to see a Full iCloud Restore happen.

Back at home:
- I connected the new iPhone-5s to computer and got Sync-ing with iTunes.
- Installed latest iCloudControlPanel 3.x
- Got Outlook 2007, PhotoStream, and the rest syncing. First by USB, then by WiFi.

Not ideal, but it worked. Like you said, no Contacts were lost (just merged between Outlook and the iPhone). At least now, as she cleans up, updates, and adds new Contacts to her Outlook ... she has the instant gratification of seeing those same changes auto-magically appear on her new iPhone (and vice-versa).
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