Note 1: I only have one local Contact setup in Outlook. I did a Full-System Backup of my Windows-10 Pro (64-bit) system (I like using Macrium-Reflect). Also, my current iCloud-for-Windows settings. I documented my Outlook Profile (and related things). I took detailed notes, but here are the abbreviated directions: TL DR – It was a fairly easy install, and everything is working fine. Microsoft Office Pro 2021 (64-bit) with Outlook-2021 (64-bit) and the latest iCloud-for-Windows v13.0 (from Microsoft Store) So, I just got finished upgrading my Microsoft Office Pro 2016 (32-bit) with Outlook-2016 (32-bit) and iCloud-for-Windows v7.21