Conditional Forwarding issues w/ tailscale

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I tried the older image you mentioned @Bucking_Horn, and the addtional dnsmasq config file with rev-server=100.64.0.0/10,100.100.100.100 works! The pihole.log output is as expected.

Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain tail1de2d.ts.net
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 64.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 65.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 66.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 67.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 68.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 69.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 70.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 71.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 72.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 73.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 74.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 75.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 76.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 77.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 78.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 79.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 80.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 81.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 82.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 83.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 84.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 85.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 86.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 87.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: using nameserver 100.100.100.100#53 for domain 88.100.in-addr.arpa
Mar  3 10:06:36 dnsmasq[359]: more servers are defined but not logged

Each needed /24 block is added individually.

I tried again with 2022.11 and it did not work. Looks like 2022.10 has the dnsmasq version where the update occurred

Update embedded dnsmasq to v2.87 by @DL6ER in pi-hole/FTL#1449

So that was great luck you happened to be using it... 2022.11 uses the next tagged dnsmasq version

Update embedded dnsmasq to v2.88test3 by @DL6ER in pi-hole/FTL#1469

I tried a quick dnsmasq config file and using rev-server=100.64.0.0/10,100.100.100.100 shows the same output as we saw with it only using 100.64.0.0/16

dnsmasq: started, version 2.89 cachesize 150
dnsmasq: compile time options: IPv6 GNU-getopt no-DBus no-UBus no-i18n no-IDN DHCP DHCPv6 no-Lua TFTP no-conntrack ipset no-nftset auth no-cryptohash no-DNSSEC loop-detect inotify dumpfile
dnsmasq: using nameserver 100.100.100.100#53 for domain 64.100.in-addr.arpa
dnsmasq: reading /etc/resolv.conf
dnsmasq: using nameserver 100.100.100.100#53 for domain 64.100.in-addr.arpa

So maybe the problem is in dnsmasq, but I barely know what I'm doing :smiley:

Edit: I did the same test with dnsmasq 2.87 and got the same output, so perhaps I'm not doing it right...