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Are you actually trying to send mail from your own smtp server? You mention apache and pihole which are completely unrelated.
No emails just routing issues.
Copy pasted but I have routing issues that neither my ISP nor the people who suffer from it can pinpoint. I’m so far down this rabbit hole that I’m assuming my IP got on a blacklist that’s sitting on some random networking infrastructure and I’m just trying to resolve all blacklist issues on the off chance that it works.
rDNS won't really help with that, it's just a DNS lookup that ties your IP to a hostname, typically used for mail server spam controls.
I'm desperate.
Have you done any traceroute runs when the issue is happening to try and diagnose where the routing issue is occurring?
Copied this from another comment I made
Do you have a different firewall/router you can try? Even just plug your PC directly into the modem for now to bypass your router and rule that out.
~~Routing to me has been solved, my router was incorrectly dropping pings on WAN because I messed up the firewall configs.~~ The trouble users still can't reach my website.
Your ISP may block 80 / 443. Try moving your webserver to an alternate high port and ask the users to test with that.
But it's only very few people. If my ISP blocks these ports, why 99% of people have no issues?
At this point I'd install wireshark and see if I'm getting their TCP connections at all.
Given your other routing issues though, I would guess you have another config issue on your firewall.
Packet capture from the router for 4 pings from him to me. ~~2 of 8 packets expected were captured and~~ have bad checksums. Disregard, all 8 expected packets do show up