I've seen numerous threads on a number of different websites with various iterations of the problem of contacts not syncing from a desktop Outlook contact folder to an Apple iPhone or iPad when using iTunes.
This may not be the solution for everyone, but I have finally solved my problem after many frustrating months.
TLDR
iTunes only recognizes contact folders to sync to an iPhone that are in the designated default eMail account of Outlook 2016 on your CPU.
BACKGROUND
- I want my calendar, notes, and email in the cloud for instantaneous synchronization between my various devices.
- On the other hand, I don't want Outlook contacts anywhere in the cloud. If a data breach ever occurs, there will be a lot of sensitive personal data floating around that I don't want out there.
- The most secure way to get Outlook contacts on my iPhone is to avoid the cloud completely and copy them directly from an Outlook *.pst folder on my CPU to my iPhone or iPad when I connect them to sync.
- I had successfully synced Outlook contacts this way with an iPhone since getting my first iPhone 3G in 2008.
SET UP
- To meet the conditions listed above, I've placed my contacts in a local *.pst folder within Outlook 2016 that is only for contacts. I don't use this account for email or calendar.
- I also use Outlook 2016 as an email client so I can review messages from Yahoo and two different Outlook.com email accounts in one email program.
- Altogether, I have the local *.pst folder for my Contacts and three email accounts configured within Outlook 2016.
- Outlook 2016 requires one account to be designated as the "default" account. If you don’t manually choose a default, it automatically designates the first account set up in your Outlook program as the default.
THE PROBLEM
- I recently upgraded my iPhone, my CPU, and my Outlook version—all pretty much at the same time.
- When everything was set up (iPhone XS, Windows 10 Home edition box, and Office 2016 with Outlook 2016, I could not get contacts to copy to iPhone.
- When in iTunes with the iPhone connected, under the SETTINGS/ INFO menu I was presented with the option to select “Sync Contacts with Outlook” and I could select the radio button that says “All Contacts.” However, my various contact subfolders did not appear under “Selected Groups” (as they always had before) and when I synced, no contacts were transferred to the iPhone.
SOLUTION
Check to see which account in Outlook 2016 is designated as the default account. Apparently, iTunes only looks for Contacts that are in the DEFAULT Outlook account. When I set up my new CPU, I didn’t pay attention to which was the default account when I put in the Yahoo and Outlook.com accounts into Outlook 2016 on my CPU. The default account was NOT the account with the contacts in it. I recently noticed this discrepancy and I changed the default account to the local *.pst account. The next time I opened iTunes, my various Contact folders appeared under SETTINGS/ INFO / Selected Groups. When I synced, the contacts were copied without any problems to my iPhone.