Keeping IT infrastructure up to date is a clear best practice. That said, we recommend delaying pfSense software upgrades to critical systems while travel restrictions (or other precautions which might inhibit physical access) are active.
While the process of upgrading pfSense is typically achieved without issue when following software upgrade guidance documentation, functionality (including VPN services) is interrupted during the process. In some rare instances, the system could be rendered unreachable, requiring onsite physical access, or via “remote hands” to remedy. Such physical access may be restricted or not be possible while travel restrictions related to COVID-19 are in effect.