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For people that think their PM's are not being sent, it's usually because they look in their 'sent items' and don't see anything there.
And THAT is because you unticked the box (or didn't tick the box) that says "save a copy of sent messages".
Over 100 PM's are sent every day through IceInSpace. I feel very comfortable that the system is working exactly as it should, with only 2 or 3 people having issues - it's very likely it's something to do with the individual (mailbox size, mailbox full, spam folder etc).
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