Postfix - Messages not showing in e-mail client (outlook)

I have a client with a Local email server in Postfix V. 3.1.4 and the following scenario happens, in specific cases, when a user sends an email from an iphone the server receives the message, by webmail it is possible to view the response in text mode, but when it arrives in the e-mail client, the message disappears and only brings the text of the previous e-mail, the reply was sent from a cell phone and the previous message came from an outlook e-mail client.
Checked antivirus and found nothing in logs (Kaspersky), checked maillog and found nothing wrong and dovecot-related error logs.

Note I'm not an expert, so I may not have tried at some point due to lack of knowledge.

Best Regards
 
Sounds like a quoting problem with the particular mail client. Postfix has nothing to do with it. What's the email client that only shows the previous Outlook message?
 
it's a FreeBSB Server
Postfix 3.1.4 is at least 5 years old. What version of FreeBSD are we talking about? I'm betting it's just as old and probably has never been updated. Postfix is at version 3.7.3 now.
 
do you use mbox format ?
some pop3 clients break with mbox format and shit happens (when some message content tricks the pop3 server about a message boundary)
 
do you use mbox format ?
some pop3 clients break with mbox format and shit happens (when some message content tricks the pop3 server about a message boundary)
mbox format, in the main.cf file the line referring to the maildir is commented.
 
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