Outbox has messages in it, but "Send unsent messages" is greyed out
I'm doing some Mailmerges and use the "send later" option. But although I can see the messages in the Outbox, the "Send Unsent Messages" option is greyed out. Also, if I restart Thunderbird, a dialog pops up asking me whether I want to send unsent messages, I click "Send now", but nothing happens; the unsent messages remain in the Outbox. The same thing happens if I create a message and use the "Send later" option. Any idea how I can fix this? It's only just started happening; previously, this feature worked just fine.
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is Thunderbird online?
In the bottom left corner of the Thunderbird screen is the indicator.
Online 
Offline 
Clicking the icon changes the state.
Thanks. It's on line, but mysteriously the 'send later' has suddenly started working again, having spent all day yesterday not working (and several restarts of Thunderbird). I hope it doesn't happen again.
I've seen this ... once I think. Like you, it just started working again.
I have this problem after doing mail merges. I use the 'Send later' option which saves the message in the Outbox on my computer (rather than on the server). I may be able to send one message using the 'Send Unsent Messages' option, but more often than not that menu link is greyed-out. If I quit and restart Thunderbird it will ask if I want to 'Send unsent messages'. It will send one more message then stop. Quitting and restarting will enable me to send another. It seems like this bug has existed for a long time. Has no-one actually found out what the problem or solution is?