Has anyone ever heard this behavior and/or have any idea what might be causing it? I have a user who reports that sometimes when he sends a message from his device, it appears to send fine, but when he goes into Outlook the message is sitting in his Outbox. If he clicks resend from there it goes out fine. This does not happen with all messages, and there is no discernable pattern (i.e. one message to a specific recipient might send fine, but another to same recipient does not). It does appear to be isolated to only composing/sending new messages; he's not seen the behavior when replying to any message from the device.
The user does not have any filters on his device. This behavior started when he moved to a Verizon unit about 2-3 months ago--he's tried different devices, but the behavior persists. His current device is an 8330 with 4.3.0.127 (I'm going to suggest upgrading his firmware but I do have several hundred other users with that exact firmware version on both VZW and Sprint devices and no other reports of this problem).
Server environment is BES 4.1.6 and Exchange 2007 SP1.

Can you do an ALT+VIEW on the sent item on the device and then cross-reference the RefID in the log files on the BES? I'm assuming he gets a check on the device, correct?

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Good call--I will have him send me that and take a look, but yeah, he gets a check on the device like it sent. Also, the fact that its actually showing up in the Outbox means it definitely hit Exchange so I'm expecting BES logs to show it as a successful send, but we'll see...

Here's what log shows:

[30112] (10/06 10:50:30.781):{0x26C0} {EmailAddress} Receiving message from device, RefId=264323381, Tag=26572736, TransactionId=-989825145

[40599] (10/06 11:05:18.008):{0x34CC} {EmailAddress} GetNewMovedMessages - Could not find folder entry id in folder list for RefId=264323381

The message itself appears in the user's Outbox folder in Outlook with the Sent Date/Time as 10/06 10:51 AM so the message has reached Exchange as expected. The second log entry above appears about every 25-30 minutes for the rest of the day but I think its not much more then a symptom. If I recall correctly, that's similar behavior to when a message is 'hard-deleted' from Outlook but remains on the device right? If that's the case, I believe it just means that BES expects that message to be in the Sent Items folder and its not.