Thanks Jon and Paul, About my computer: SquirrelMail version 1.4.9a (from src/login.php) Plugins installed: GPG Plugin v 2.1 gpg (GnuPG) 1.4.9 PHP Version 5.2.6 Web Server version: Apache/2.0.63 Courier-IMAP 4.3.1/i386-portbld-freebsd5.3/Mon Jun 23 04:39:26 MDT 2008 SMTP server version 1.03 qmail OS FreeBSD 5.3-RELEASE-p37 I'm also using procmail to sort incoming and tmda to exclude spam. The system has moved several times and the box it is on now has had some recent upgrades. ----- I have several issues that I will summarize to help understand what to tackle first. 1) GPG fails to encrypt on send. I can decrypt incoming and the keyring management seems to be OK. This problem resulted from the recent move and/or update of the software. Before the move it was working. 2) GPG inserts "character entities" into the to: and subject: fields. This is an old problem that moved across installations and through the upgrade from an earlier GPG version plugin. I've never had that right but just worked around it. I want to fix that. 3) I was unable to get tmda-tools plugin to work right. 4) I want to automatically add to ~.tmda/lists/whitelist on compose. Perhaps tmda-tools can do this. 5) I want users to be able to change system passwords. I tried some plugins but failed to make that happen. ---- First, I think should get the GPG working. I have set debug=1 When I try to encrypt outbound lots of debug output gets puked out. It looks normal to me except this part: opengpg - executing "/usr/local/bin/gpg --command-fd 7 --status-fd 5 --no-tty --yes --openpgp --homedir /path/to/www/www.******.com/html/mail/data/shanesmith.gnupg --homedir ../../data/shanesmith.gnupg --always-trust --force-mdc --armor --encrypt -r 'st*******@****s.com' ''" ... gpg return status: 2 ... Error can't open `': No such file or directory Error : encryption failed: file open error Error GPG Plugin: No cyphertext was generated. ... (I've obscured some path info that should not become part of the history of the internet. The complete output I can show in private if that helps.) The command line passed to GPG has that last parameter empty ''. Is that the file that won't open? Why is the --homedir defined twice? Bother definitions are correct relative to the gpg plugin directory. Thanks for your consideration. I certainly do appreciate the help. Shane ------------------------------------------------------------------------- This SF.Net email is sponsored by the Moblin Your Move Developer's challenge Build the coolest Linux based applications with Moblin SDK & win great prizes Grand prize is a trip for two to an Open Source event anywhere in the world http://moblin-contest.org/redirect.php?banner_id=100&url=/ ----- squirrelmail-users mailing list Posting guidelines: http://squirrelmail.org/postingguidelines List address: squirrelmail-users@xxxxxxxxxxxxxxxxxxxxx List archives: http://news.gmane.org/gmane.mail.squirrelmail.user List info (subscribe/unsubscribe/change options): https://lists.sourceforge.net/lists/listinfo/squirrelmail-users