I searched and read a few things but I’m special…well, dumb. First I’m a total newbie. Second, I’m somewhat new to vision loss and have difficulties navigating as I’m not extremely proficient using a screen reader and dealing with all its quirks and mishaps. So forgive me if this is a widely known and simple issue that I should have been able to resolve on my own.
Expected Behaviour:
I just installed pihole on a headless pi zero 2w. It s up and running well with the exception of all my iCloud email no longer loading on any of my devices. I have mail, privacy protection, protect mail activity turned off on my iPad/iphone/mac. Mail will open, then state that it’s downloading x number of new messages, but they never download. If I turn off pihole blocking temporarily, all my devices can load mail properly. Switch blocking back on and mail stops loading again. I read somewhere about a setting (adding a folder and entering a line using the cli not the gui) to set mask.iCloud.com blocking to false or something to that effect. I’m confused as there are seemingly conflicting posts about this. I don’t want to bypass pihole and I also don’t want to not have any extra security when away from and on cell service. I do see that mask.iCloud.com is being blocked on the gui. Could someone please layout a clear and simple answer for a dumb, blind person such as myself on exactly where, and how to fix this and what exactly happens if I do or don’t (ie less secure email when away and on cell, etc). I am enjoying the pihole ad blocking (ads are super frusterating when you’re blind and use a screen reader where the focus jumps every time an ad pops and you lose your place). For the time being I just temporarily switch of blocking when I want to pull emails, but that’s somewhat tedious. Thank you for your time!
Yeah, I read that doc. Part of why I’m confused. I do not have an iCloud+ sub, and do not have this private relay function enabled (although I can’t find anything that says “private relay” anywhere in any settings on these devices). The browsers (safari) work flawlessly on all the devices. It’s only mail, specifically using apple mail (my preference as it works well across all devices using a screen reader). I installed the gmail app and it works perfectly, but I’d rather get back to using apples mail if I can get it to work again. It can see how many new messages I have available. It just gets stuck at downloading messages. If I temporarily turn off blocking, messages start downloading again.
Now that I’ve been googling this a bit more, it appears that it’s a problem with the latest iOS updates (18.2 phone, 15.2 Mac) breaking mail with pihole. I found a Reddit starting a few weeks ago (back when they released the new iOS with mail sorting by category). Disabling pihole allows mail to be retrieved. Some say that setting the block iCloud pr to false gets mail to work, but then allows ads?it’s confusing, especially to a newbie, that’s dumb and blind.
Not sure about anything with Private Relay, but I have had email issues with iOS/iPadOS 18.2. Configuring my devices to bypass Pi-hole for DNS did not resolve the issue, so not sure it is really Pi-hole related.
Been in touch with Apple Support, and worked with them for a while. They are aware of issues with mail and 18.2, and supposedly working on a solution. Who knows when that will happen. Time will tell.
Yeah, that’s a bummer. A couple people on Reddit were speculating that some of the changes in mail on 18.2 (categories and logos) may be using private relay even if you have it disabled or are not using it. It also sounds like it affects some people differently. For some, mail is just incredibly slow. Others, mail doesn’t ever load. For some, bypassing pihole allows mail to load. Others not. For some adding the block iCloud false line works. Others not. Someone even said that an uninstall/reinstall of mail worked,and again for others not. Like you said, it sounds like an Apple issue. My luck, being a newbie to pihole and just installing it the other day, to have a problem like this on startup. I guess we’ll wait and see what happens. I wouldn’t doubt that people are right in suspecting that the downloadable logos and categorization are using PR. Being blind and using a screen reader, having logos in my mail isn’t really something I’ll ever need. Ha
Seems like this is this case. Working fine before I installed pihole, and with pihole disabled, at first glance (knee jerk reaction) would point to pihole. But dig in a little and it appears to be something that changed on apples end. The downside though, if you are a cynic as I, is that I’m sure this isn’t a high priority item on their end.