Using Classic Outlook on Windows for personal email, calendar, and contact management
Hello Robert,
Good day!
Thank you for posting to Microsoft Community. We are happy to help you.
Based on your description I understand that you want to “reply to the message with attachment included”.
Usually we suggest that you copy and paste the attachment while reply to the message, or drag attachment or insert it.
However, as you mentioned, “Not asking about copy paste, or drag in or forward. Simple reply with attachment”. After thorough research and testing, it’s been concluded that the feature you are inquiring about replying to the message with attachment included is not feasible.
Nonetheless, If you set up attaching original mail, the attachment will appear in the attached original email. Hence, you may try this way as follow.
Open Outlook --> Go to File-->Options-->Mail-->Scroll down to replies and forward --> replies --> Select attach original message
We apologize if we are not able to meet your requirements; however, thank you for bringing this to our attention, we will surely raise you concerns to our Product Team and hopefully this can be included in the future updates.
Sincerely,