<< I owe 9K to Uncle Sam for 1999. Out of this 9K, 3K is tax due on Roth IRA conversion
(spread over four years).

I also owe $300 tax penalty. Is it possible to claim a waiver on the tax penalty? I was goin to
request that Roth IRA conversion as the main reason for underpayment of taxes. What are the
possible reasons for which IRA would waive the penalty? >>

You may not owe a penalty. You should have had your total withholding to at least equal last year's tax (safe harbor-no penalty). If not, you had something unusual to cause the underpayment besides the Roth. If that "something" came later in the year, Marti's suggestion to do the AI schedule of Form 2210 will help. Your tax preparer, or software should offer this alternative. If not, try the quarterly tax estimater on www.edcosoft.com. You can figure the penalty on the 2210 AI and attach it to any prepared 1040 and change the penalty amount to correspond. Ed