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This plugin I made for my own use but I thought this may be useful for you also.

Skype - is an instant messaging applicaiton.
Cropper - Cropper is a screen capture utility writeen in C#. It makes it fast and easy to grab parts of your screen

Usually you will use cropper or some other utilities or method to create screenshots and save it to disk. Then send to a buddy by using file transfer feature of Skype.

Here, I have used Cropper plug-in template and Skype Skype4COM API to build the plugin. Still it is not complete due to some incapabilities of Skype API.

The working of the plugin is -

1. After you capture the screen (double click) 
2. You will be asked to choose a user (all active chat window users will be listed)
3. Now, a file open dialog will be shown with probably only current screenshot (! - inability of skype)
4. You choose the file and file transfer begins when the other user accpets
5. the file in pioint 3 will be deleted automatically after transfer is complete

Here are the installation and usage instructions:

1. Download and extract the zip file to your Cropper plugins folder. Most probably it will be at X:\Program Files\Fusion8Design\Cropper\plugins.
2. You can see three files in the zip file: 1) SendToSkype.dll 2) Interop.SKYPE4COMLib.dll and 3) Readme.txt. (Readme.txt you may simply delete)
3. Plugin is ready 

Now usage:

1. After you invoke cropper, right click somewhere on the selection box.
2. Click Output - SendToSkype
3. Over!
4. Double click to capture screen
5. If you have not started skype, you will get a message "Start skype first"
6. If you do not have any active chats happening you will get message "No active chats available"
7. If you have atleast one active chat, you will get a user selection box. Click Ok to continue or you can cancel transfers by closing the window.
8. If you click 'ok', you will be promted to choose a file. Select the last saved file which was displayed in the browse window.

Notes:

• This plugin I wrote just for my use. I do not know what are your requirements
• Use it at your own risk. I am not responsible.
• If you like this plugin, let me know through comments. I will extend this to an excellent project .
• This is not a commercial product.