how does ubuntu manage my ssh / gpg keys changes betweet reboots?

Hi linuxquestions. I have ssh keys (in ~/.ssh) and gpg keys (in ~/.gnupg) with Thunderbird and enigmail but I get very odd behavior when trying to use them. All this is on Ubuntu 14.04.1

When I reboot how both work changes

SSH

• ssh keys is forgotten and I have to enter key password for each and every ssh connection

or

• ssh keys password is remembered and I am not prompted for password when I ssh.

GPG

• When using enigmail, I am given the basic gpg-agent interface where I am limited to remembering password for x minutes

or

• I am given advanced password management where I can "remember for x minutes", "remember until logout" "remember forever"

There seems to be no patter as to when this happens, I could reboot 3 times in a row and have to enter ssh key password and on the 4th if would happen that everything works. It also can be in any combination of the above behaviors.

Would anyone know where to look or how to fix this so that ssh key passwords are always remembered and I get the more advanced gpg options