How did you setup the accounts? It looks like you got some settings wrong. Here is instructions on how to set them up properly:
Hotmail & Outlook 2003
1. If you have a free Hotmail account, upgrade it to Hotmail Plus by clicking the Upgrade link under Hotmail Options.
2. If you don’t yet have a Hotmail account, you can get one by visiting the Microsoft Online Services Home page listed under External Links in this article.
3. Configure Outlook by creating a new E-mail account. For Outlook 2003, click Tools, E-mail Accounts, Add a new e-mail account, and select HTTP as the Server Type. For Outlook 2007, click Tools, Account Settings, New, and select the Microsoft Eachange, POP3, IMAP, or HTTP option. Click Next.
4. Enter your Name, Hotmail E-mail address, and Password.
5. For Outlook 2003, make sure you clear the Log on Using Secure Password Authentication (SPA) checkbox.
6. Click Next, then Finish. Outlook will synchronize with your Hotmail account the next time it checks your e-mail.
As far as I can tell Mail.com’s free service does not allow pop access to the account. Maybe from your support options it will list the options but not in mine.
You can try removing this account and see if it resolves your issue.
Not sure whether you should use Outlook for pop3. I believe outlook express does a better job. In our office here we only have one service setup on the our Microsoft Outlook client which is Exchange server. We use no other pop3 client because of conflicting issues.