Hello, Thank you for contacting Just Answers, my name is Sherry.
This issue is usually caused by a message stuck in your Outbox. To resolve this, delete all of the contents of your Outbox Folder before sending another message. Please reconfigure your account in Windows Live Mail to refresh the connection to our server, check out the links below on how to do this: Remove account from WLM
Configure a Windows Live Hotmail account in Windows Live Mail
you are using firefox and not outlook correct?
Walk through this
Open the Windows Live Mail application.
Click "Add Email Account" from the left-hand menu bar. If the option is not available, click the menu icon in the top right side of the window and select "Show Menu Bar." After the menu bar has appeared, click "Tools" and "Accounts." Your Live Mail accounts will be listed here. Select the button labeled "Add" and select an email account.
Type in the email address for your Charter account. If you would like Windows Live Mail to remember your password, you can type in your password XXXXX well, but this is not necessary. Type in your name or user name. Check the box that reads "Manually configure server settings for this account."
Ensure that the incoming mail server is set as POP3. This is the email technology that Charter uses to provide services to email clients. Enter "pop.charter.net" into the incoming server box and ensure that the port is set to 100. Also ensure that both of the boxes labeled "This server requires SSL" are unchecked.
Type in your login ID. The login ID is equal to your Charter user name, which should be everything before the "@" sign in your Charter email address. For example, if your Charter address isXXX@XXXXXX.XXX, then the login ID should be pepper. Ensure that the "Log on using" dialogue is set equal to "Clear text authentication."
Set the outgoing server to SMTP.charter.net. Make sure that the port number is XXXXX to 25 and that the check box next to "My outgoing server requires authentication" is unchecked. Click "Next" and then "Finish."
For you isp you need to change that pop.charter.net to wahtever your settings should be