Open Windows Mail 2008/2009.
If the File menu containing the Tools menu isn't visible along the top of the program, we'll have to toggle it on. Click the button to the left of the (?) question mark button near the top right and click the Show all menus option. This will toggle the File menu and we will be able to click Tools at the top.
Click Tools and then click Accounts.
Click on the email account to highlight the account we need to edit and then click Properties.
Make sure the email address field contains the full email address and that there's a check in the checkbox at the bottom that states Include this account when receiving mail or synchronizing.

Click on the Servers tab at the top.
Fill out the fields accordingly:
  • Take note of the account type listed in the first field. (POP3 or IMAP)
  • Incoming Mail Server: mail.yourserver.org
  • Outgoing Mail Server: mail.yourserver.org
  • E-mail username: Enter the full email address (ex: john@yourserver.com)
  • Password: Enter the password for the email account.
  • Do NOT check the box that states Log on using Secure Password Authentication.
  • CHECK the box that states Outgoing server requires authentication.
Click Settings to the right.
This small window will pop-up on top of the properties window, make sure the dot is in the first option, Use same settings as my incoming mail server and click the OK button then click on the Advanced tab at the top.
On the Advanced tab, fill in the fields accordingly:
  • Check BOTH boxes on this screen that state This server requires a secure connection (SSL)
  • Outgoing mail (SMTP): 587
  • Incoming mail (POP3 or IMAP): 993 for IMAP, 995 for POP

Click Apply then click OK.
They should now be back on this screen. Proceed with editing other yourserver email accounts if necessary, otherwise click Close to finish.
Incoming (IMAP)
Server: mail.99w.us
Port: 993
SSL: Yes
Username: Your @99w.us email address

Incoming (POP)
Server: mail.99w.us
Port: 995
SSL: Yes
Username: Your @99w.us email address

Outgoing (SMTP)
Server: mail.peak.org
Port: 587
SSL: Yes
Authentication: Enabled