Hi JcW32,
Totally normal behavior you're seeing there. Even though Office 2019 is already activated with your Microsoft Account, it’ll still show a “Sign In” prompt when you’re using a local Windows account. That prompt is mostly for cloud features like OneDrive, syncing settings, or accessing recent files across devices.
If you’re just using Office for basic stuff like editing documents or spreadsheets you can ignore the sign-in prompt. Everything will still work fine.
But if you ever want to use those cloud features, it’s best to sign in with the same Microsoft Account you used to activate Office. Just avoid signing in with a different account, as that could cause license issues.
Hope this clarifies the confusion here.