I get email in Outlook WebApp. I also happen to hate Outlook WebApp.

What I want:

  • Have outgoing emails (sent in the past) forwarded to Gmail
  • Have those emails grouped in their appropriate thread/conversation
  • Not have the emails text contents inside attachments (which happens with certain messages)

What I have:


  • Have a centralized location to search for old outgoing messages
  • Save OWA space by being able to delete outgoing messages from thrre

Failed attempts

  • Forwarding sent mail using Apple Mail
  • Redirecting sent mail using Apple Mail

1 Answer 1


How does Gmail decide to thread email messages? Having the same subject isn't enough; the In-Reply-To header must also be present.

ReplyWithHeader for Apple Mail works for manually forwarded email, but not for rules.

This AppleScript solves the issue (for a single use):

set recipientEmail to "[email protected]"
set recipientName to "John Doe"
tell application "Mail"
    repeat with msg in messages in sent mailbox
        set outgoing to forward msg without opening window
        tell outgoing
            make new to recipient with properties {name:recipientName, address:recipientEmail}
        end tell
        send outgoing
        exit repeat
    end repeat
end tell

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