@mkeenan I had a similar OS message recently. The shortest/safest path may well be to open a free ticket at go.netgate.com and have them send you the firmware, and install it via USB stick. I have gotten past odd warnings before but this time it borked and I had to recover manually.
If you've installed a package from the current repo onto an old version that may try to install dependencies from the later version.
Otherwise see https://docs.netgate.com/pfsense/en/latest/troubleshooting/upgrades.html, maybe set to "previous version" and install that first, and work your way up. 2.4.4 is pretty old. I think I started with 2.4.2 on the one that had to be reinstalled. IIRC it worked to get to 21.02 but then even though it offered 21.05 it "installed" 22.01 and was left half upgraded with the wrong OS.
HTH,