I often refer to these two pieces when debating rebooting a project from scratch: Joel Spolksy Things You Should Never Do Part 1 http://www.joelonsoftware.com/

I often refer to these two pieces when debating rebooting a project from scratch: Joel Spolksy Things You Should Never Do Part 1 http://www.joelonsoftware.com/articles/fog0000000069.html http://www.joelonsoftware.com/articles/fog0000000069.html Darmesh Shah How To Survive a Ground-Up Rewrite Without Losing Your Sanity (a response to essay #1 13 years later) http://onstartups.com/tabid/3339/bid/97052/How-To-Survive-a-Ground-Up-Rewrite-Without-Losing-Your-Sanity.aspx http://onstartups.com/tabid/3339/bid/97052/How-To-Survive-a-... It's not always cut and dry when you should start over, but if you are make sure you are doing it in a way that starts presenting customer/user value ASAP.