Can, may, and should, are all treated differently. The taxpayer can pretty much do anything they want to, even if it is subject to penalty and/or excise tax and/or income taxes. I thought I already mentioned that there is a recommended strategy to leave Roth earnings year-over-year, knowing full well it incurs tax and/or penalty, because the person making the recommendations thinks you will easily beat the 6% penalty in the earnings. I would point out if that is true, why not just make that a regular investment?

I suspect the IRS would find a lot of retirement mistakes, if they had the personnel to investigate anything.