Pi-Hole impact on emails

[Bob_pyke]

The issue I am facing:

Since installing an RPi hosted Pi-hole Ive noticed emails do not display pictures with associated links that can get me to the website. I whitelisted the domain for the linked site, which worked only once. I like everything the Pi-Hole is doing, but don’t want it to filter my emails or associated links, and when I whitelist a link, I need it to work all the time thereafter.

Details about my system:

RPi 3 hosting Pi-Hole

What I have changed since installing Pi-hole:

Just white lists.

Thanks,
Bob

[jfb]

These tools can help you determine which domains are being blocked that interfere with your content:

How do I determine what domain an ad is coming from?

Block ads or fix broken sites This FAQ is written in the context of finding out how to block an ad that isn't blocked automatically, but the same steps can be used to troubleshoot issues with sites that don't function properly. An example is that sometimes certain payment gateways try to collect metrics on the sale, but these domains are blocked by Pi-hole, so the payment cannot be processed. Also, some links send you through several referrers and if one of them is blocked, you may land on a …

What OS is the client on which you are viewing emails running? MacOS has some particular settings to get emails to load.

Edit:

Please upload a debug log and post just the token URL that is generated after the log is uploaded by running the following command from the Pi-hole host terminal:

pihole -d

or do it through the Web interface:

Tools > Generate Debug Log

[nprampage]

Had a similar issue on my Apple devices through Pihole. Are you seeing this issue on Apple devices?

Mine was resolved I think by using the information here: BUG - IOS15/MacOS Monterey - Apple Mail Security 'your network settings prevent content from being loaded privately' - Help - Pi-hole Userspace

Specifically, I set BLOCK_ICLOUD_PR=false, and it worked for my situation.