I Can't Send Pictures in Pidgin
Sending images through the instant messaging client Pidgin is sometimes tricky. Your success will depend on several factors, including your IM protocol and server. If you're having trouble sending images, check if the protocol you use supports image transfers. In addition, some protocols require you to open a direct IM connection before you can send an image to another user.
About Pidgin Protocols
Pidgin supports a host of different popular messaging protocols, including AOL Instant Messenger, MSN Messenger and Google Talk. Some protocols support the direct transfer of images, whereas others don't. In addition, though certain open protocols such as XMPP support the transfer of files, the actual implementation is handled by a particular server, which may not allow for file transfers. Gmail, for instance, implements XMPP but doesn't support file transfers, so sending a picture to someone via their Gmail handle is impossible.
Direct IM and Insert Image
To use Pidgin's "Insert Image" command, you must connect directly to another client. To do so, you must use a protocol that supports Direct IM, such as AIM. After that, you can connect directly through your buddy's chat window, under "File" and then "More." The other person will have a chance to accept or refuse the connection, and after the connection is established you can use the "Insert" button to show an image directly to your friend.
Other Ways to Send Pictures
Even if you're not using a protocol that allows you to insert an image into a message directly, you can still send pictures to others using the "Send File" function. You must use a protocol that supports sending files, but if you use this function, you don't need to open a Direct IM session. You can send files to others by right-clicking on their name in the Buddy List and selecting "Send File..." before choosing a file to send. They will have to accept the file transfer before it can begin.
The only protocols that support the "Insert Image" function in Pidgin are GG, ICQ, MXit, MySpace, Sametime, SILC and AIM. Other protocols, including IRC, Bonjour, Yahoo Messenger, MSN and XMPP, support file transfers but not direct image transfers.