I've been migrating some of my Raspberry Pis from Bullseye to Bookworm recently. The wired hosts come through OK (even an ancient Raspberry Pi B that I turned into a poor man's JetDirect a while back), but I've had two hosts connected by WiFi drop off the network during the apt-get distupgrade. One is a GPS-disciplined NTP server on a RPi 3B+ that I got working again by plugging in a monitor and keyboard long enough to reconfigure WiFi.
Another host that's gone catatonic is a CM4 running OctoPrint on one of my
3D printers. That one's on a Waveshare CM4-NANO-A that brings out USB and GPIO, but not HDMI. I'll have to move that onto a different adapter board that brings out HDMI as well as USB, which is on order...but having to do this is a bit annoying. The printer will work without it (its controller board has a MicroSD slot and can print from that), but it's not as convenient as telling PrusaSlicer to send a file to OctoPrint. (First-world problem? :) )
Has anyone else noticed this issue when upgrading to Bookworm on a WiFi-connected Raspberry Pi?