I solved the problem myself. I didn't change none of the settings in ~/.profile. I simply looked into the Error Console of Thunderbird (I never paid any attention to that before) and saw the following output: <snip> Error: [Exception... "'Failure' when calling method: [nsIEnigmail::initialize]" nsresult: "0x80004005 (NS_ERROR_FAILURE)" location: "JS frame :: chrome://enigmail/content/enigmailCommon.js :: GetEnigmailSvc :: line 212" data: no] Source File: chrome://enigmail/content/enigmailCommon.js Line: 212 </snip> I read the source file and saw that on line 212 it was getting information from the settings. I noticed that sometimes in my TB (Thunderbird) settings I would have to press Esc for it to show up. F10 wouldn't work. So I thought I would specify the path to gpg-agent instead. That gave an error concerning the option --charset=utf8. I then unchecked the box to specify the GnuPG path and clicked OK. I clicked on OpenPGP in the file menu and scrolled to "About OpenPGP" It still had the gpg-agent path. So I pressed Esc, and wow the enigMail preferences popped up with the box checked on specify GnuPG path. I unchecked the box again clicked ok and promptly pressed Esc. I went back to the OpenPGP file menu and scrolled back to "About OpenPGP" and low and behold it complained about not finding the program. Having a vague idea what needed to be done, I went back in to the Preferences of enigMail and checked the box for specifying the GnuPG path and put it to /opt/local/bin/gpg2 like I had wanted to do all along. Pressed the OK button, followed by pressing the Esc key, and voilá my problem was solved with a quick check to "About OpenPGP". Now, to really test that I had made progress, I opened a mail that I kept around because I knew it was signed, and the program worked like it should. Then I sent signed messages to myself. Then I composed this message saved it in Drafts, quit TB, restarted TB, and then sent this message to the list signed. Well, it failed with the failing to initialize enigmail, I checked the path and it was correct, so I changed it back to gpg-agent, clicked on "About OpenPGP", and then changed it once more back to /opt/local/bin/gpg2, looked in "About OpenPGP", saw all was well, and then I added this updated information and sent the message signed. I have opened a bug report with the enigMail project on enigmail.mozdev.org so I will update it with what I have written here and that is it for now. I think TB likes to activate and run gpg-agent itself before it can believe the program to exist in daemon from the terminal. -Altoine