"Send to: Mail recipient" context menu not working

The Send to ... Mail Recipient uses the MAPI\Send Mail association, or the Send mail command.

The Microsoft Mail app only contains an association for the MAILTO protocol, so you can't set it as a recipient of the Send mail command.

If like me you are having this issue trying to send photos from from desktop explorer to an Outlook recipient in Windows 8.1 / Office 365. Use this link but be sure to use 'Joseph's Script' it's an easy fix. Hope this helps somebody.

Thanks to Slipstick Systems for saving me another day of searching forums for the answer.

http://www.slipstick.com/outlook/create-a-custom-send-to-shortcut/

Joseph’s method uses a windows script and allows you to select multiple files and attach them to a new message, preserving your signature and stationery settings.

To use, open Notepad then copy this code and paste it in to notepad. Save it as SendToMailRecipient.vbs. You can either save it in the SendTo folder or save it elsewhere and create a shortcut to it to place in the SendTo folder.

Option Explicit
Dim objArgs, OutApp, oNameSpace, oInbox, oEmailItem, olMailItem
Dim a, oAttachments, subjectStr, olFormatHTML
olMailItem = 0
olFormatHTML = 2
Set objArgs = WScript.Arguments 'gets paths of selected files
Set OutApp = CreateObject("Outlook.Application") 'opens Outlook
Set oEmailItem = OutApp.CreateItem(olMailItem) 'opens new email
For a = 0 to objArgs.Count - 1
Set oAttachments = oEmailItem.Attachments.Add(objArgs(a))
subjectStr = subjectStr & Right(objArgs(a),Len(objArgs(a))-(InStrRev(objArgs(a),"\"))) & ", " 'recreates the default Subject e.g. Emailing: file1.doc, file2.xls
Next
If subjectStr = "" then subjectStr = "No Subject "
oEmailItem.Subject = "Emailing: " & Left(subjectStr, (Len(subjectStr)-2))
oEmailItem.BodyFormat = olFormatHTML
oEmailItem.Display

By the way hit the windows key+R and enter " shell:sendto " to take you straight to the folder where you will need to save the file, be sure to use the right file extension (not txt) it's all in the instructions on the link above.

Wild idea : I wonder if this is a case of a metro app not available from the desktop.

If this is the case, you would need another mail client.