Steve on 29 Apr, 2018 10:55 AM
welcome to the GPGTools support platform. Sorry you are having problems using GPG Suite.
First things first: GPGServices offers two variants of encryption. Symmetric (password only) and asymmetric (stronger and based on public key cryptography). As soon as you tick the option to "Encrypt with password" you are using symmetric encryption. If you keep the "Add to Recipients" check box ticked as well, you are usign both symmetric and asymmetric encrpytion and that is where things can become confusing.
You can use any random password for symmetric encryption. Obviously if you encrypt a file or message with your OpenPGP key (asymmetric) you will instead be asked for the password for your OpenPGP secret key (which is required for decryption).
So I suggest to refrain using symmetric encryption.
Next: you can store the password for your OpenPGP key or cache it for a certain time. Please see this KB-article on how to manage passwords for your keys.
Since you may have used on of the two options you are not asked for your password when decrypting the file.