- Open Settings > Profile name > iCloud > Private Relay > Disable the feature.
- Open Safari > Settings > Websites > Pop-up Windows > Choose Allow next to While visiting other websites > Select Allow for outlook.live.com.
- Open Safari > Settings > Websites > Manage Website Data > Search outlook > Remove.
Basic Fixes
- Check internet connection: Check whether you are getting optimum internet speeds on your Mac.
- Check Outlook server status: Visit DownDetector to check if Outlook servers are working fine in your region.
- Force quit and relaunch Safari: Click the Apple logo > Force Quit > Safari > Force Stop.
- Change DNS on your MacBook: We suggest switching to Google DNS on your MacBook to get better speeds.
- Update macOS to update Safari: Open Settings > General > Software Update.
Fix 1: Disable iCloud Private Relay
Open Settings > Profile name > iCloud > Private Relay > Disable the feature .

Fix 2: Allow Pop-ups for Email Links
You need to allow pop-ups on Safari for any links that you open using your Outlook account. By default, Safari can block pop-ups in the browser.
Step 1: Open Safari > Go to Outlook > Click on Safari > Settings .
Step 2: Click on Websites > Pop-up Windows > Choose Allow next to While visiting other websites > Select Allow for outlook.live.com .

Fix 3: Remove Extensions
Some Safari extensions might be the reason behind Outlook not working in Safari. We suggest removing those that you don’t use anymore or the ones that don’t receive regular updates.
Open Safari > Settings > Extensions > Select an extension and uninstall it till the problem gets solved.

Fix 4: Clear Outlook Cache
Lastly, you can try clearing Outlook website cache from Safari. This will remove all your preferences and login data.
Open Safari > Settings > Websites > Manage Website Data > Search outlook > Remove .

Tip: Learn how to turn off AdBlock in Safari .