The file transfer will start once they accept. You will also see a message in the conversation window where you can click on a link to cancel the file transfer if your contact is not responding.
Your contact will then receive a notice that will ask them if they want to either accept (Alt + T) or decline (Alt + D) your file. Select a file to send, and click Open to send it. To send a file to a contact, start a conversation and then click on the Send a File or Photo link on the sidebar on the right. You can also receive files from your contacts as well. While you are chatting with your contacts using Windows Messenger, you have the ability to send them a file at any time.
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