Email, Messaging, & Video Calls Email How to Exchange Instant Messages in Windows Live Hotmail by Heinz Tschabitscher Writer A former freelance contributor who has reviewed hundreds of email programs and services since 1997. our editorial process Heinz Tschabitscher Updated on June 24, 2019 Gary Waters / Getty Images Email Yahoo! Mail Gmail Tweet Share Email The instant you get an email, you're ready to reply — instantly. Instantaneously, you can expect an answer from the original sender moving the conversation forward. In Windows Live Hotmail, you can move this instant messaging to, well, instant messaging if you're both signed in to Windows Live Messenger (in a dedicated application, on the web, or inside Windows Live Hotmail). Exchange Instant Messages in Windows Live Hotmail To send somebody an instant message in Windows Live Hotmail: Make sure you are signed in to Windows Live Messenger in Windows Live Hotmail (see below).Go to your Contact list in Windows Live Hotmail.Make sure the desired contact's icon glows green to indicate they are available in Windows Live Messenger.You can also send messages when the icon glows red (busy) or orange (away), but the recipient may not be able to respond immediately.Send an email instead.Click the contact's icon.Select Send an instant message from the menu.Type your message in the window that pops up.Hit Enter or click Send to send. To reply to an email with an instant message: Click the small green square in front of the sender's name or email address in the opened message.If the square is red or orange to indicate the sender is busy or away respectively, it is better to reply by email.Also, do reply by email unless an instant message is clearly superior (if you're trying to pick a movie to watch, for example, or need an immediate answer). Sign In to Windows Live Messenger in Windows Live Hotmail To log on to Windows Live Messenger on the web through Windows Live Hotmail: Click Messenger in the Windows Live Hotmail toolbar.Select Sign in to Messenger (Web) from the menu.