I ran into a problem upgrading pfsense 2.4.3_1 to 2.4.4 due to a dependency on the old PHP 5.6.x from the older package of FRR .2_2 (Free Range Router.) The problem was that PHP56 was marked as vital due to the FRR dependency, and it was not possible to update FRR to .2_4, as FRR .2_4 needed pfsense 2.4.4 (I could not decide whether this was a modern O. Henry story or a missing epilogue from Catch 22.)
The fix:
1. connect to the pfsense server with SSH
2. Open a shell
3. Run this command:
pkg set -v 0 php56
Your upgrade should work - I had to do a couple of update attempts before it worked.
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