Now this was surprising. I had to update a project and I guess it's been over a year since I've started Android development.
Apparently Android SDK only signs the debug certificate for a year. This can be a bit annoying because you have to uninstall all your testing apps after you create a new debug certificate.
- First up, open up Windows Explorer and paste in "%HOMEPATH%\.android"
- Locate "debug.keystore" and delete it
- Now back in Eclipse, hit Project > Clean in the menu
- You should now have a new debug certificate.
If you want to make the certificate last longer, see the Androidian link below for steps on creating your own certificate.