I have some [sensitive] software like Putty, FileZIlla, and more on an encrypted VeraCrypt/TrueCrypt volume.
As the volume is mounted after login, it is also AFTER the Windows Firewall is initialized.
As far as I was informed in the Microsoft forums, a rule is ignored if the program does not exist when the firewall starts.
It is suggested (and maybe GlassWire could offer a feature for that) that a restart of the firewall service can solve this without the need to remove/readd the rule again.
Regards