how can I force recipients of my emails with attachments, to reply with the attachment when they reply. I'm using Outlook 2013.


These are not foolproof so you will sometimes have to re-add the attachments after you get a reply.

Method 1

Create a template with Reply and ReplyAll actions disabled. The responders are forced to use Forward. You will probably find only the original mail is affected.

Prevent e-mail message recipients from using Reply All or Forward

"This feature requires both the sender and recipient to be using Microsoft Outlook."

Method 2

Disable actions with VBA. You can use this on any mail not just the first.

How To Easily Disable ReplyToAll And Forward In Outlook

"To be clear. This technique does NOT send macros in your email. It only flips a metadata bit in the message and that metadata is only transmitted within Exchange (within your company). It is not propagated to outside email addresses."

Sub NoReply_NoReplyAll()
    ActiveInspector.CurrentItem.Actions("Reply").Enabled = False
    ActiveInspector.CurrentItem.Actions("Reply to All").Enabled = False
End Sub

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