This happens because a saved MSG file is not really an email message that's in your mailbox. When you open an MSG file and you click Reply All Microsoft Outlook thinks it is a file it does not think it is an email from your mailbox. As a result Microsoft Outlook may put the address in the To field it may put the From address of the MSG file in the To field. This is why you get this problem with MSG files in Microsoft Outlook.
Why this happens:
MSG files don’t retain full account context (like the original mailbox or sending account), so Outlook can’t properly map the reply fields.
Workarounds:
• First drag the MSG file into your Outlook mailbox folder, then open it and click Reply All.
• Or manually correct the To/From fields before sending.
Better approach:
Use a tool like
Softaken https://www.softaken.com/msg-suite to import MSG files. This way replies will behave normally.
• You can process MSG files, at once.
• It supports conversion without any data loss.
• The tool keeps all email properties intact.
These properties include attachments, formatting, subject sender details and timestamps. The tool also provides a demo version that allows you to convert a limited number of emails per folder.