@bkmDanno
You should apply for the 4868 extension, then wait a day before you file. The rollover will be reported to the IRS using the date when Ameritrade processes the transaction, not the date when you request it. If they take a few days, you could still end up being late. Making financial transactions on a tight deadline is always dangerous. If you get the extension, you will have protected yourself against any bank delay that is beyond your control.
