First Way:

If you start a chat session with someone on your contact list and you don't see the handwrite tab under the message entry field, you have to install additional software to get "Ink".

Probably the easiest way to turn the handwrite capabilities on is downloading Microsoft Journal Viewer version 1.5. Make sure that you sign out and exit Messenger before you run the Setup program. The installation installs the Journal Viewer program and the "Ink" the handwrite feature of Messenger requires. Note that the Journal Viewer has a security issue (KB886179) and it is recommended to download the security update for the Viewer and install it as well.

After you installed the Journal Viewer and the security update start MSN Messenger and sign in. You should now see the handwrite tab and be able to draw a message with the mouse. You can use the tabs to switch between "handwrite" and "type" mode. Also, just typing a message when in "handwrite" mode switches to "type" mode.

Note that in handwrite mode you have to click on the Send button to send your drawing. Just pressing Enter to send a message, as in type mode, doesn't work. Another feature that doesn't work in handwrite mode is dropping a file on the send area. You have to switch to type mode first if you want to send a file to your chat partner

Second Way:

MSN Handwriting is an add-on for MSN Messenger Plus! just like InfoPan. If you have already installed InfoPen, we would advise to switch to MSN Handwriting, because: it is only 2.5 MB big (compare to 18 MB of InfoPen), it has no 30-day trial period, and you don't see it runnin' in background as it is just a normal plug-in for MsgPlus! Its very easy to install this addon. The one thing you really need is Messenger Plus!. After you installed Messenger plus download MSN Handwriting. Once you downloaded MSN Handwriting install the files you downloaded (See the readme.txt). Once installed open a conversation window. Now you will see under where you normally type your text some new buttons: