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Outbox has messages in it, but "Send unsent messages" is greyed out

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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.

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.

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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.

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I've seen this ... once I think. Like you, it just started working again.

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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?