July 12, 2018

Outlook is rubbish!


Microsoft Outlook especially older versions is junk, but you probably knew that already.

For some reason Outlook often sends out a message with incorrect syntax e.g. “[email protected]”.

Mail servers like postfix will reject these messages but Outlook will not warn its user that there is a problem. Instead it will keep the message in the outbox and continously retry sending.

If you are a postfix admin you can strip the apostrophes with a command filter.

Here is how: Your log will have a message like warning: Illegal address syntax from server.example.net[192.0.2.20] in RCPT command:<'[email protected]'>

create a file outlookfix.regex and ad the content below: /^RCPT\s+TO:\s*<'([^[:space:]]+)'>(.*)/ RCPT TO:<$1>$2

Edit /etc/postfix/main.cf and add the line: smtpd_command_filter = pcre:/etc/postfix/outloofix.regex

Execute postfix reload

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