When Outlook won't connect to the outgoing server, it's usually because the firewall is blocking Outlook. This can happen with any firewall and seems to be most common after an update is installed. This is often because the Firewall is checking the Outlook version, not just for Outlook.exe.
Task 'email@example.com - Receiving' reported error (0x80042108) : 'Outlook cannot connect to your incoming (POP3) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).'
Windows 7 or Windows 8
If you are using windows 7 or Windows 8 default firewall, you should be asked if you want to allow Outlook access the first time you run it. You can check your settings by going to Control panel and searching for Firewall. (Firewall is under System and Security Category.)
Click the link on the left of the firewall panel to allow apps through the firewall.
Find Outlook in the list of applications and verify that is it checked to allow access. If you use a desktop computer, you generally only need to allow it on private networks, but laptops will need both private and public networks enabled.