New Thunderbird user here - ended up on this Bug after enabling this setting 
desiring a more familiar sending experience where the actual sending of the 
message and filing into Sent is handled _ascynchronously_. However, after a few 
days of use, I noticed that although mail was sent for the first little while 
after starting up the application, eventually it would stop sending messages. 
Only solution was to toggle online status, or restart the application at which 
point I'd be prompted to send out any unsent messages.
Have turned the "send in background" feature flag back off and now mail is 
sending reliably as I compose each message.

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https://bugs.launchpad.net/bugs/810769

Title:
  Sending window distracting and interrupts flow

Status in Mozilla Thunderbird:
  Confirmed
Status in thunderbird package in Ubuntu:
  Confirmed

Bug description:
  When sending an email in Thunderbird a small dialog box appears to say
  the message is being sent and this affects the flow of interacting
  with your email. In almost every case I move the focus away from that
  window and go to my INBOX.

  My recommendation would for the window to not show and to show this
  information in the status bar (similar to how it works in Evolution).

  ProblemType: Bug
  DistroRelease: Ubuntu 11.10
  Package: thunderbird 5.0+build1+nobinonly-0ubuntu5
  ProcVersionSignature: Ubuntu 3.0.0-5.6-generic 3.0.0-rc7
  Uname: Linux 3.0.0-5-generic i686
  Architecture: i386
  Date: Thu Jul 14 14:59:20 2011
  InstallationMedia: Ubuntu 11.04 "Natty Narwhal" - Alpha i386 (20110202)
  ProcEnviron:
   LANG=en_US.UTF-8
   SHELL=/bin/bash
  SourcePackage: thunderbird
  UpgradeStatus: Upgraded to oneiric on 2011-07-13 (1 days ago)

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