I am using the MSN protocol with my buddy. No matter what I do or not matter what options I change, I can never pick the option, Insert Image either from the conversation menu, or the menu above the message box. I've been in the preferences window looking at the formatting for the message box, and the option insert is available in there. I push it and it will insert an image that looks just fine. I know this is just a box separate from the chat but why wouldn't it work in the normal chat. I've used the custom smiley option to show an image of 64x64 in size. It showed up perfectly. My buddy actually uses the real MSN messenger, and has sent an in window image that has shown up perfectly. I am using the newest version of Pidgin - 2.6.6.0. I don't know why I can have a custom smiley show what I want but not able pick the insert image button. This sounds like a simple fix in the code itself.

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