I have QuickBooks Simple Start 2008 (Plus Pack) and it works fine for my small business. It no longer will download updates. Do I need to upgrade or is there something else I should do to get updates?
There could be two causes for this issue:
Your firewall or application installation prevents you from updating it using the online servers.
The software is discontinued, and the update servers don't have the files anymore.
Luckily, there is a page provided by Intuit where you can see all the details regarding end of life for certain products, upgrade, contact, etc.
As I can see, the 2008 version isn't supported anymore, and an upgrade might be required.