Why am I seeing Your network settings prevent content from loading privately in the mail apps after updating Pi hole?

After updating Pi-hole, users may encounter an error message stating "Your network settings prevent content from loading privately in the mail apps." This issue occurs because Pi-hole blocks certain domains that are required by the Mail app to load content securely.

To resolve this issue, you need to:

  1. Whitelist the following domains in Pi-hole:
    • *.outlook.com
    • *.hotmail.com
    • *.live.com
    • *.office365.com
    • *.yammer.com
    • *.sharepoint.com
  2. Flush your DNS cache:
    • sudo service pihole-FTL restart

After completing these steps, restart the Mail app and you should be able to load content privately again.

  • Can I use Pi-hole with other email clients besides Mail? Yes, Pi-hole can be used with any email client that supports DNS blocking.
  • Why does Pi-hole block these domains? These domains are used by Microsoft for telemetry and tracking purposes.
  • Is it safe to whitelist these domains? Yes, it is safe to whitelist these domains as they are required for the Mail app to function properly.
  • How can I prevent this error from happening again in the future? You can disable Pi-hole for the Mail app or exclude the Mail app from using Pi-hole's DNS blocking feature.
  • Can I automate the process of whitelisting these domains? Yes, you can create a script or use a third-party tool to automate the process of whitelisting the required domains.
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