The biggest estimation effort I ever took part in was a whole-system rewrite[1] where we had a very detailed functional test plan describing everything the system should do. The other lead and I went down the list, estimated how long everything would take to re-implement, and came up with an estimate of 2 people, 9 months.

We knew that couldn't possibly be right, so we doubled the estimate and tripled the team, and ended up with 6 people for 18 months - which ended up being almost exactly right.

[1]: We were moving from a dead/dying framework and language onto a modern language and well-supported platform; I think we started out with about 1MLOC on the old system and ended up with about 700K on the rewrite.