If you copy a sent text with emoticons and paste it twice in the convo textbox by mistake and try to corrected pressing CTRL+Z (undo)... you will see that you have to press it twice because in the first try the emoticons of the second string pasted are going to be disabled...

Windows 7 Ultimate (6.1.7600)
Windows Live Messenger 14.0.0726
Messenger Plus! Live 4.83.0.372
Skin: Messenger Live Toolbox 5.1

Thats normal in the sense that after the text is inserted into the chat window the emoticons are parsed. Try copying :) into a window. Its the same behavior.

It's by (Messenger's) design, like when you want to undo Word's auto correction. Even when you type and press ctrl-z the smile face is reverted to text :) too.

And there is no way to skip that step to make the process look more clean?

Why break standard behaviour? It is only one more press of CTRL+Z...

Note that this whole behaviour of reverting back to the characters :) when you pasted also only happens in certain situations (depending on how you pasted the emoticons, if there was text before, and even if you have used CTRL+Z before or not, etc). Thus trying to break this standard behaviour to make it more 'clean' might actually break a lot more stuff than fixing anything.

That's a good point cookie...