Outlook 2007/2010 - First time iCloud setup and config for heavy Outlook user

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The SlipStick blog is great, but I just discovered this forum. I thought my iCloud setup voyages (as well as being new Apple/iOS user) might be better discussed in this forum. I hope it's ok, but to give my thread some context, I'm going to copy my blog-posts and Diane's excellent responses so far. http://www.slipstick.com/outlook/icloud-and-outlook-problems/#comment-178501

I hope to continue discussion in this thread:

Excellent blog. Thank you so much for compiling all this information. My setup:

Windows 7-64 Ultimate SP1

Outlook 2007 SP3

iPad2 16gb WiFi-Only iOS v5.0.1

I live in Outlook and have for about 10 years (been carrying-over my PST file). It’s currently about 3gb is size. I backed up PST file before turning on iCloud Control Panel’s Outlook Sync. PhotoStream and IE Bookmarks were already turned-on and working.

Due to amount of email items (filed away and otherwise) I was thinking of just syncing Contacts, Calendar, and Reminders/Tasks (single iCloud Mail option switched off on iPad2) . If I want email from this time forward, I figure I would just add required POP3 accounts to iPad2 and get a copy there as well. Is this a valid config? Is the only problem that Tasks linked to emails don’t appear in Reminders?

I’m very protective of my PST file. I don’t care for the way it has manipulated my DataFiles. I’m already thinking of using my backed-up PST file to try to put things back. However, it would be great to have my above Outlook data synced to my iPad and future iPhone5.

I’m reading about iCloud 1.x vs 2.x . Sounds like it might be linked to iOS version? I suppose I really should update iPad2 and I’m sure iPhone5 will come with latest. I was also thinking of switching over to the offered @iCloud.com domain. Seems like both changes would have wide-spread ramifications (kinda why I’ve been avoiding them).

Would it be a good idea to restore Outlook 2007 PST file and put Outlook back the old way. Upgrade Outlook 2007 to 2010. Upgrade iPad2 to iOS6. Migrate from @me.com to @iCloud.com. Upgrade iTunes to latest. Get that all working again, THEN try setting up iCloud Outlook Sync?

There are 2 main questions above. Thanks again for your help. I can send some PayPal $ if you want.

Diane Poremsky July 31, 2013

Email won't sync over iCloud - it would need to be moved into an IMAP account to sync. You plan sounds like a good one to me (it's how I do it). Calendar, contacts, tasks/reminder - i don't use my me.com address for real mail so i quit setting it up in iCloud.

Flagged messages don't work well with apple/iCloud - I recommend creating tasks instead. 9I have a macro around here that can create a task from a message when you flag it.)

Yeah, iphone 5 will have ios6, soon to be 7. I don't think you need to change from @me to @iCloud addresses - both domains should be on the same server - unless maybe you have an old mobileme account that was not migrated.

If you current pst is messed up, then restoring a backup can be helpful, but it doesn't sound like it got messed up, and iCloud should mess it up, save for moving calendar and contacts out of the pst and into the iCloud.

I'd definitely use the newest iCloud with outlook - its a lot more stable and less buggy.

Re: Outlook 2007/2010 - First time iCloud setup/config for heavy Outlook user

RE: Email … Thanks for the clarification. I now see that iCloud Mail switch on iPad itself does something else. Good to hear I’m on the right path. Still not sure why it iCCP says "Mail" when email isn't synced (unless it's just talking about IMAP accounts).

RE: Tasks. Yes, that’s the only way I see around it. It’s just so easy to tag the email but I’ll check out the Macro.

RE: No, it’s a recent account. I thought @me and MobileMe was the same. On mine, I think it would just be a matter of setting up an Alias (like you can on Outlook.com). The wife had an old MobileMe account we migrated ... maybe that's what threw me off.

RE: PST … I went ahead and turned the Outlook option off in iCCP to see what would happen (and told it to save data). It actually did a pretty good job of putting everything back the way it was. I ended up with a few duplicated Tasks, but no data was lost. I still restored my old PST.

I did then have a little problem getting the Outlook sync option in iCCP to stay off. Also, iTunes WiFi Sync (mainly for music) seem to still think I'm using iCloud syncing Outlook items when I'm currently not.

I then tried-out Outlook Hotmail (Outlook.com) Connector. It seems to modify the PST files in a similar way. So, it seems that’s the only way to do cloud syncing without an Exchange server. I guess I'm going to just have to accept it and move forward. It's notes also said something about some Outlook versions not syncing Tasks. I thought a Microsoft solution (to match my desktop OS) was worth exploring (and not picking cloud provider based on end devices ... iPad2 and iPhone5). I think my Android tablet wouldn't be left out that way. I'm probably going back to iCloud though ... it's just "cleaner".

As we know, iTunes has some Outlook sync but who wants to be running iTunes all the time when you can have iCloud (basically effort-less real-time) functionality.

So, what determines the iCloud version? Is it just the iCloud Control Panel version? I’m using the latest 2.1.2 (actually

Also, can someone please verify that with iCloud, I can get Windows-7 Outlook-2007, iPad2, and iPhone5 all syncing together (and changes will propagate between all).
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