Hello Justin S. Regula,
I'm sorry to hear that you're having trouble downloading your contacts from your iPhone to Outlook. It's possible that there may be a compatibility issue between your iPhone and the version of Outlook you're using. However, upgrading to Windows 11 is not necessary to sync your contacts.
However, there is another specific channel for your mentioned concern where you will get some possible information for certain specific resources and platform from our related community members.
I understand your concern but since your problem is related to Outlook for iOS, I would also like to suggest you post your concern in the related community i.e., Ask a question - Get in-app help for Outlook for iOS and Android - Microsoft Support to get the detailed help from the experts.
Apologies for redirecting you to different community as the members in the category posted focus on the users with out of the box concerns on Microsoft 365 and have limited knowledge on the Outlook for iOS; so, to get the fast and better assistance, we have redirected you in the correct path.
Appreciate your patience and understanding. Have a great day!!
Best Regards,
S M Nazmun Nur
