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




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