I have this issue too, though it's not as persistent as Danai SAE-HAN's copy; it gives up after exactly five prompts (exactly six for drafts), then gives an error ("Sending of message failed" or "Unable to save your message as draft").
I spliced together a template from reportbug for relevance (I use pinentry-gtk2 for the password entry). Package: enigmail Version: 2:0.95.0+1-3 Package: pinentry-gtk2 Version: 0.7.3-1 -- System Information: Debian Release: lenny/sid APT prefers testing APT policy: (500, 'testing'), (500, 'stable'), (50, 'unstable') Architecture: i386 (i686) Kernel: Linux 2.6.18-4-686 (SMP w/1 CPU core) Locale: LANG=en_US.UTF-8, LC_CTYPE=en_US.UTF-8 (charmap=UTF-8) Shell: /bin/sh linked to /bin/dash Versions of packages enigmail depends on: ii gnupg 1.4.6-2 GNU privacy guard - a free PGP rep ii icedove 2.0.0.9-3 free/unbranded thunderbird mail/ne ii libc6 2.7-4 GNU C Library: Shared libraries ii libgcc1 1:4.2.2-4 GCC support library ii libnspr4-0d 1.8.0.14~pre071019b-0lenny1 NetScape Portable Runtime Library ii libstdc++6 4.2.2-4 The GNU Standard C++ Library v3 ii libglib2.0-0 2.14.3-1 The GLib library of C routines ii libgtk2.0-0 2.12.1-1 The GTK+ graphical user interface ii libncurses5 5.6+20071124-1 Shared libraries for terminal hand ii libpango1.0-0 1.18.4-1 Layout and rendering of internatio enigmail recommends no packages. -- no debconf information -- To UNSUBSCRIBE, email to [EMAIL PROTECTED] with a subject of "unsubscribe". Trouble? Contact [EMAIL PROTECTED]