I was having issues with the upgrades to my pfSense box, where the UI just said "Unable to check for updates":
I logged in to the box, and tried
[2.3.4-RELEASE][email@example.com]/root: pkg update Shared object "libssl.so.8" not found, required by "pkg"
Yeh, no good. Poking around a bit, I did the following, which seems to have resolved the issue:
[2.3.4-RELEASE][admin@yggdrasil]/root: pkg-static update -f [2.3.4-RELEASE][admin@yggdrasil]/root: pkg-static upgrade -f
Why the UI isn't using the statically compiled "pkg" binary is unknown (i.e. a mystery, i.e. likely a bug :-).