Hi Saad Ulaby,
The "still working" hang before even reaching a password prompt can have different causes depending on the account type. Here are a few things worth trying:
It's always a good idea to go to Help > Check for Updates and make sure Outlook is fully current before anything else.
For iCloud: Outlook should open a browser window to sign in with your Apple Account directly. If that window never appears, try making sure iCloud Mail is enabled on your Mac: Apple menu > System Settings > iCloud > iCloud Mail (toggle on), then give it another go.
For Comcast.net: It may be worth checking first whether your account has been migrated to Yahoo Mail. Xfinity began this transition in June 2025. Simply go to Yahoo and enter your Comcast email. If it's recognized there, you'd add it in Outlook as a Yahoo account instead. If it hasn't moved yet, these IMAP settings should work:
- Incoming: imap.comcast.net | Port 993 | SSL/TLS
- Outgoing: smtp.comcast.net | Port 587 | STARTTLS
For Outlook.com: If possible, try adding this account on a different network (such as a mobile hotspot) to rule out any local network or firewall interference.
A few general tips that often help:
- Add accounts one at a time, restarting Outlook between each attempt
- Try a full Force Quit before retrying (right-click Dock icon > Force Quit)
Since you're already in touch with Microsoft Support, sharing the detail that it's "stuck on 'still working,' browser window never opens, Version 16.108 / build 26041219" should really help them narrow things down on their end.
Hoping this helps move things forward. Please don't hesitate to follow up if you need anything else.