I'm planning on moving Pi-hole from Raspbian running on my Raspberry Pi 3 Model B+ to a Dell OptiPlex 390 running x64 Debian 9.9 (which is officially supported.) Any pitfalls or considerations I should be aware of?
Nope. If you kno0w how to use raspbian you know how to use Debian.
pi-hole doesnt care if it is on Debian or raspbian but be sure to install stretch and not buster
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