Without thinking or reading to the last paragraph of this article, I went and started a dist-upgrade on my pi.
Curious now to see if it still boots after it's finished.
Edit: Oops
~ » ssh pihole@172.16.0.1
Last login: Wed Oct 11 09:38:31 2023 from 172.16.0.96
compdump:print:36: write error: no space left on device
compdump:print:42: write error: no space left on device
compdump:print:44: write error: no space left on device
compdump:44: write error: no space left on device
compdump:print:44: write error: no space left on device
compdump:44: write error: no space left on device