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messages in outbox get stuck and wont send
 
So I have a few vacation filters setup and when I get over 50 messages in the outbox it gets stuck and wont send.
I try Send Queued mail and it returns Nothing to send even if I select all the messages.

What can I do ?
 
There is also a timed macro in each reply as well.
 
I also get the "nothing to send".

Even modified the message, but still can't send it.
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