I had exactly the same issue happening to me! I’ve since added a Real Time Clock (RTC), so the Pi shouldn’t forget about the current time anymore. That is until the battery runs out of course, for which there is no monitoring in place. So yeah maybe I should disable DNSSEC as well. At least we need to get better at building fault tolerant systems. Maybe Pi-Hole needs to be aware of and handle this scenario better: a special “we’re booting up and we don’t have the current time so don’t do DNSSEC yet”.