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Problems with mail delivery are normally related to the remote server. So far, every time someone has reported a mail delivery problem (and we get at least one reported at least once a week) when we've looked in our logs we've found that the message was successfully delivered to the remote server. At that point there's nothing FastMail.FM or your mail client can do--it's up to the remote server to complete delivery. We've got to the point now where we're not inclined to spend hours scutinizing the logs to diagnose mail delivery failure reports, because after doing it dozens of times we know the problem won't be at our end...
The only thing to be aware of with OE in particular is that if it can't send a message it will remain in Local Folders->Outbox until you choose Tools->Send & Receive->Send All. If it's in the Sent Items, in our experience, it generally means that it has been sent to FastMail.FM's SMTP server successfully. And if it's got to our server, then it will definitely be sent to the remote server, unless the remote server is down. If the remote server is down FastMail.FM will keep trying it for 24 hours before it gives up and sends you make a delivery failure message.
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