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In previous versions of Windows Live Messenger, it was possible to send an image in a conversation, either by dragging the file into the window or by pasting the image into the message box.

In the Windows 8 version, neither of these techniques work. How do you send a picture?

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Are you referring to the built in "messaging" app? –  Jared Tritsch Oct 9 '12 at 18:13
    
Yes, I am. Am I wrong in thinking that the Messaging app is the same as Live Messenger? –  andypaxo Oct 9 '12 at 18:20
    
@andypaxo - install the desktop version of the messaging application. The built-in application is at best the Metro version which given its not even been given a final release has lots of missing features. –  Ramhound Oct 9 '12 at 18:26
    
Agreed with Andypaxo. The messaging app is intended to be chat only across many platforms. They may roll out that feature in a later release, but at current it is purely text. –  Jared Tritsch Oct 9 '12 at 19:22

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Yes this Metro Messages program is still very basic and adding attachements does not work so far (just in Mail App it does). We all need wait for an update...

Until then, install the "old" desktop version of the live messenger

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As of 2013, Microsoft is transitioning Live Messenger users to Skype.

I'd advise anyone in this situation to install Skype, and sign in with the same account they used for MSN / Live Messenger. The interface is much nicer, there's both a desktop and Modern UI / "Metro" version.

This is what I'm doing now, although it wasn't an option when the question was originally asked.

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