For me, after an update sometime in May evolution forgot POP passwords between 
restarts, and while running would ask for keyring the password when sending or 
receiving mail.
I fixed it by editing ~/.gnupg/gpg.conf
I deleted the line starting with "gpg-agent-info".
I added a line containing only "use-agent"

When I restarted evolution, I was presented with only one keyring password 
dialog.  I entered the password, then unlike before was not bothered with any 
more password dialogs.
When I restarted evolution yet again, there were no password prompts, even 
after clicking "Send and Receive".

My ~/.gnupg was created under Debian, and I believe the May evolution
update was the fist time GPG was utilize in my Ubuntu system.

-- 
Evolution "forgets" POP3 passwords after sending GPG-signed mails
https://bugs.launchpad.net/bugs/228794
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