Using the New Outlook for Mac features in business environments
Dear MattJRogers,
Thanks for using Microsoft products and posting in the forums!
It sounds like you're experiencing a sync issue between Outlook and your iPhone. This can indeed be confusing and frustrating.
Here are some reasons and steps for your reference:
1, Check Account Type: Ensure that your email account is set up as an Exchange/outlook.com account on Outlook and your iPhone. IMAP or POP accounts may not sync properly. To check this on your iPhone, go to Settings > Accounts & Passwords > Add Account > Choose Outlook.com (Exchange) > Sign in and turn on Contacts sync.
2, Check for Updates: Ensure that both your Outlook app and iPhone are running the latest software updates. Sometimes, updates can fix sync issues.
3, Re-add Account: If the issue persists, try removing and re-adding your email account on your iPhone. Go to Settings > Mail > Accounts > Select your email account > Delete Account. Then, add the account again using the steps mentioned in point.
4, If you still have an older version of Outlook (legacy Outlook) installed on your computer, you can try switching back to the older version, which is also currently supported and will be more suitable for your personal use.
Best regards,
Harris-MSFT |Microsoft Community support specialist