To actually scrap and start over?
When the current code doesn't do what you would like it to do, and would be cost prohibitive to change.
I'm sure someone will now link Joel's article about Netscape throwing their code away and how it's oh-so-terrible and a huge mistake. I don't want to talk about it in detail, but if you do link that article, before you do so, consider this: the IE engine, the engine that allowed MS to release IE 4, 5, 5.5, and 6 in quick succession, the IE engine that totally destroyed Netscape... it was new. Trident was a new engine after they threw away the IE 3 engine because it didn't provide a suitable basis for their future development work. MS did that which Joel says you must never do, and it is because MS did so that they had a browser that allowed them to completely eclipse Netscape. So please... just meditate on that thought for a moment before you link Joel and say "oh you should never do it, it's a terrible idea".