...
I have a reoccurring issue with our user community, and I'll bet pot brownies to poundcake that this is a common issue with a common fix.
On a regular basis, a message gets stuck in the POP queue when downloading new mail.
I'll be that this is because if an error in M$'s error handling in Outlook, OE for Wintendos and Macs, and Entourage for Mac the common thread being M$.
If you can, get a hold of one of those troublesome messages and examine it using 'od -c'. Courier's POP server prints a '\r' character before every '\n' character. If your MTA stores messages with CRLF line ends, then Courier's POP server will send CRCRLF to the clients. MS clients don't seem to like that much. You need to configure your MTA to normalize messages, so that they are stored with just LF line ends. I haven't heard how you'd do this with Postfix. One option would be to migrate to Courier's MTA. You might be able to just use maildrop as the MDA, but I'm not sure if it normalizes the line ends... Perhaps Sam can clarify that.
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