Unsupported OS on Raspbian 9

Still getting the Unsupported OS when using Raspbian 9 on a 3B+. It's pretty annoying, to say the least. I've got to go update all of my scripts to skip this check which has been failing for over 2 years now with no fix in sight. Give me a sec and I'll give you the expected dig result, but it's what you expect it to be, so no clue why it fails

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

dig -t txt versions.pi-hole.net returns:

../../../../lib/isc/unix/net.c:581: sendmsg() failed: Operation not permitted

; <<>> DiG 9.10.3-P4-Raspbian <<>> -t txt versions.pi-hole.net
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 24068
;; flags: qr rd ra; QUERY: 1, ANSWER: 1, AUTHORITY: 0, ADDITIONAL: 1

;; OPT PSEUDOSECTION:
; EDNS: version: 0, flags:; udp: 1232
;; QUESTION SECTION:
;versions.pi-hole.net.		IN	TXT

;; ANSWER SECTION:
versions.pi-hole.net.	300	IN	TXT	"Raspbian=9,10,11 Ubuntu=16,18,20,21 Debian=9,10,11 Fedora=33,34 CentOS=7,8"

;; Query time: 47 msec
;; SERVER: 192.168.42.254#53(192.168.42.254)
;; WHEN: Sat Mar 12 17:24:09 EST 2022
;; MSG SIZE  rcvd: 136

The sendmsg() failure is because I have IPv6 disabled. It's always been there. It's equally annoying, but doesn't seem to have anything to do with pi-hole.

Debug token: https://tricorder.pi-hole.net/cGWr4RpB/

Something is blocking the dig to our nameserver:

*** [ DIAGNOSING ]: Operating system
[i] dig return code:  0
[i] dig response:  ../../../../lib/isc/unix/net.c:581: sendmsg() failed: Operation not permitted
[✗] Distro:  Raspbian
[✗] Error: Raspbian is not a supported distro (https://docs.pi-hole.net/main/prerequisites/)

Yes, I have IPv6 disabled. It's some weird behaviour on Raspbian that it always tries IPv6 first, even when it's explicitly disabled in the OS. However, you should see it try IPv4 afterwards. That's what the dig above shows.

I run Raspbian and have not experienced this in a similar configuration

Grrrr. Didn't have IPv6 actually disabled. There's yer problem. Just had it blocked in firewall.
Still got pihole not working with the latest version, but we'll start anew tomorrow to see what's wrong.

It is expected to fail if your dig response includes the line

../../../../lib/isc/unix/net.c:581: sendmsg() failed: Operation not permitted

We do not do any special filtering of the dig output. If it does not contain the expected result, the whole check will fail.

The solution is outside of the scope of Pi-hole: you need to fix your system. As soon as your dig won't include the offending line, it will succeed.

Yep, the symlink got broken for /etc/sysctl.d/99-sysctl.conf, so IPv6 wasn't actually disabled. Seems like Raspbian was still using it under the hood as a result, and the firewall was explicitly blocking it. Thx for pointing me in the right direction.

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