Bypassing security is never a good idea, especially when you're dealing with company Networked assets.
Some Networks (such as schools) don't permit SSL because packets can't be monitored for content.
For what it's worth:
Most common problem:
Right click tray time> "Adjust..."> Update.
While here, tick 'Automatic synchronize...'
Another situation:
"On board" browser certificates not current.
Vista/Win7: Go to your "Windows update" in IE8^
For XP: IE8> Security > Windows Update.
When @ Microsoft Updates, click the 'Custom' button, not the 'Express'.
This will give you hardware & software updates specific to your unit.
Includes specific drivers & "Root Certificates".
["Express" and "Automatic Updates" only gives Windows operating system updates]