iTunes sync on a new computer - any issues to be expected?

Commodore

Senior Member
Outlook version
Outlook 2019 64-bit
Email Account
IMAP
On the new computer I've already installed Office '21, and iTunes is in the pipeline also. The PST files will be moved from the "old" computer. Should I expect any issues when doing the first iPhone-Outlook sync on the new computer (such as double entries or completely messing up all contacts and calendar events, etc., on either iPhone or Outlook side)?

I mean, the data should be the same on both sides at that point (syncing on the old computer prior to that). But I know the system keeps some "sync counters" or something like that somewhere...

I'd like to stay on the safe side. A related past experience (the other way around, tho') never filled me with confidence: When doing the first sync of a new iDevice, despite choosing "Replace information on this iPhone..." to populate the new iDevice cleanly with what's in Outlook, and despite setting "Do not sync events older than 90 days", the first subsequent sync would always find somehow somewhere a few weird sync conflicts in certain contacts and calendar events (usually some events older than 90 days even...).
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
On the new computer I've already installed Office '21, and iTunes is in the pipeline also. The PST files will be moved from the "old" computer. Should I expect any issues when doing the first iPhone-Outlook sync on the new computer (such as double entries or completely messing up all contacts and calendar events, etc., on either iPhone or Outlook side)?

I mean, the data should be the same on both sides at that point (syncing on the old computer prior to that). But I know the system keeps some "sync counters" or something like that somewhere...

I'd like to stay on the safe side. A related past experience (the other way around, tho') never filled me with confidence: When doing the first sync of a new iDevice, despite choosing "Replace information on this iPhone..." to populate the new iDevice cleanly with what's in Outlook, and despite setting "Do not sync events older than 90 days", the first subsequent sync would always find somehow somewhere a few weird sync conflicts in certain contacts and calendar events (usually some events older than 90 days even...).

Well, I suggest you keep some good notes (I know I do, as I only do this every 3-5 years).

I live-in Outlook and heavily rely on Apple ecosystem and iCloud.

I'm getting ready to uninstall my Outlook-2016 / MSO-2016-Pro (32-bit) so that I can upgrade to Outlook-2021 / MSO-2021-Pro (64 bit). I then plan to re-login-to iCloud for Windows v7.21 (Apple downloaded stand-alone installer). Get everything working in Outlook-2021 (64 bit) and have two-way-sync of Contacts. Also want my iCloud Drive, Photo-Library, and Photo-Stream, working ... as well as my Google Chrome Bookmarks syncing again.

After you get Outlook installed and your Accounts and related items setup (if new machine or they are just missing), then you can work on getting your old Folder.PST file migrated and working (I've found there is a certain way to do it). Then, you can work on finishing the iCloud stuff.

See this:
and this:
 

Commodore

Senior Member
Outlook version
Outlook 2019 64-bit
Email Account
IMAP
No iCloud here. Just offline direct iDevice-PC sync with iTunes. Therefore Contacts and Calendar in this case (as they still haven't "figured out" how to sync Tasks and Reminders :rolleyes: ).
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
1. No iCloud here. Just offline direct iDevice-PC sync with iTunes. Therefore Contacts and Calendar in this case

2. (as they still haven't "figured out" how to sync Tasks and Reminders :rolleyes: ).

1. Gotcha. Yeah, I used to do it that way years ago (before I completely understood how iCloud works and it's benefits). Yes, doing it that way it is pretty easy to duplicate some of your Contacts and/or corrupt your Contacts in general.

You might have gotten the wrong idea about iCloud and Outlook from my old posts. It actually works great most of the time (I was just having some isolated problem which eventually cleared). Also, I manage to keep it working for my wife also (on her separate accounts, computers, iDevices, etc.).

2. It's actually not that big-a-deal for me now that those (and also Notes) are iCloud-enabled now-days and can be shared and accessed that way.
 

Commodore

Senior Member
Outlook version
Outlook 2019 64-bit
Email Account
IMAP
Nah, I just sometimes like to sacrifice comfort for security and privacy. ;) Maybe I'll switch to iCloud some day.

So does the iCloud sync observe the setting "Do not sync events older than 90 days" for calendar (if there's such thing there as well)? If so, do calendar events older than that in iCloud get deleted automatically (and remain locally in Outlook)?

How's the compatibility with Notes and Reminders/Tasks, any issues there?
 

Commodore

Senior Member
Outlook version
Outlook 2019 64-bit
Email Account
IMAP
Well, seems everything went through quite well. Other than Outlook being "smart" on its own, changing my default .pst data file to outlook.com "exchange" account... so afterwards I thought the local iTunes sync wasn't working any longer (and curiously there were way too many holidays in my calendar all of a sudden). And when it was already too late, I noticed that my iPhone stuff got synced to outlook.com :eek: (which I don't really use). Fixed everything back.
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
Nah, I just sometimes like to sacrifice comfort for security and privacy. ;) Maybe I'll switch to iCloud some day.

So does the iCloud sync observe the setting "Do not sync events older than 90 days" for calendar (if there's such thing there as well)? If so, do calendar events older than that in iCloud get deleted automatically (and remain locally in Outlook)?

How's the compatibility with Notes and Reminders/Tasks, any issues there?

We got the wife a new computer, so I just completed a clean-install with Outlook-2021 (64-bit) and iCloud for Windows v13.0 ... everything seems to be working and Syncing to my Apple-iCloud data.
Email, Contacts, Calendars. I think even Reminders are working now. Also Photos, iCloud-Drive, and Chrome Bookmarks Sync to Apple Safari.

Notes are not in Outlook for Windows, but they are in the iCloud, so I can bring-up the same ones on my iPhone, iPad, Mac, and even Windows via iCloud.com . You can also Reminders for "notes" if they just-must be in Outlook.
 

PhilBurton

Senior Member
Outlook version
Outlook 2013 64 bit
Email Account
IMAP
I have no additional suggestions here as such. However I am very concerned that Apple has announced that it is deprecating Calendar and Contact syncing, at least for Windows iTunes. (So why oh why should I continue to use iTunes.

Further I am in the process of replacing iTunes with a third-party program for media syncing, music, books, podcasts, etc. For several years now I have had real problems in this area, and finally I'm motivated enough to simply banish iTunes from all the systems in my home network.
 

Commodore

Senior Member
Outlook version
Outlook 2019 64-bit
Email Account
IMAP
Was there any new/recent announcement from Apple in this regard? Last thing I remember is that they removed these features from Mac, but decided to leave it on Windows indefinitely.

It goes against my "local first" principle, so I guess I'll also have to look into other options, if the need arises. What 3rd party solutions have you considered so far? iMazing? (But I think they still need at least some parts of iTunes to be installed.)
 

PhilBurton

Senior Member
Outlook version
Outlook 2013 64 bit
Email Account
IMAP
Quote
Was there any new/recent announcement from Apple in this regard? Last thing I remember is that they removed these features from Mac, but decided to leave it on Windows indefinitely.

It goes against my "local first" principle, so I guess I'll also have to look into other options, if the need arises. What 3rd party solutions have you considered so far? iMazing? (But I think they still need at least some parts of iTunes to be installed.)
I will try iMazing along with some other potential utilities. I also have a "local first" and a "local only" perspective. Comcast just nailed me because I went over the 1 TB limit for downloading in a month. My penance is download speed so slow that even email won't load. Using the cloud a lot is just asking for trouble.
 
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