SOLVED: iTunes not syncing Outlook Contacts
This may not be the solution for everyone, but I have finally solved the problem of not being able to get Outlook contacts to transfer to my iPhone for 18 mos.
TLDR: iTunes will only find contacts to sync to an iPhone that are in the designated default eMail folder in your Outlook desktop installation.
BACKGROUND: I don't want my Outlook contacts in the cloud—no Office 365, no iCloud, no Skydrive, no Google Drive…nothing. Sooner or later there will be a data breach and there will be a lot of my personal data floating around that I don't want out there. IMO, the most secure way to get Outlook contacts on my iPhone is to copy them directly from my Outlook 2016 *.pst folder on my CPU to my iPhone when I connect the two to sync. Yeah, I know low tech...but much lower long term risk. I had successfully synced Outlook contacts this way with an iPhone since I got my iPhone 3G in 2008.
SET UP: I have my contacts in a local *.pst folder that is only for contacts. I don't use this account for email or calendar. I also use Outlook as an email client so I can review messages from Yahoo, and two
different Outlook.com email accounts with one email program. So, I have the local *.pst folder for my Contacts and three email accounts configured with my Outlook installation. Outlook requires one of the accounts to be designated as the default email 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: About 18 months ago, I needed to upgrade my iPhone, my CPU, and my Outlook version—all pretty much at the same time. When everything was set up (iPhone XS, a Windows 10 Home edition CPU, and MS 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.” But 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: It’s all dependent upon which account is selected as the default account in Outlook. Apparently, iTunes only recognizes 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 the 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.
iPhone XS