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

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