For long I have been very frustrated, that Enigmail wouldn'y remember my
passphrase, prompting me for it every time I send or receive encrypted
emails. I have searched and asked, but have not - until a few minutes ago -
found the reason or a solution (this is probably due to my lack of
knowledge).
I had no idea that this was related to the fact that I am running XFCE, which
happens to be the case. By chance I discovered that under Settings ->
Sessions and Startup -> advanced you can tick a box saying: launch GNOME
service at startup. This triggers the Gnome keyring daemon to run upon boot.
I added my discovery to the manual:
https://trisquel.info/en/forum/enigmail-does-not-ask-automatically-decrypt