Life and Death Planning for Retirement Benefits

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Chapter 5: Roth Retirement Plans 255
January 1, 2010, would be the first date in 2010 on which an amount could be distributed
out of a traditional IRA; therefore the earliest possible date for a “2010 Roth conversion” would
be January 1, 2010 (same-day conversion of a January 1 distribution). The last possible date in
calendar 2010 on which an amount could be distributed out of a traditional plan would be
December 31, 2010. Therefore the last possible date for a “2010 conversion” would be 60 days
after December 31, 2010 (the deadline for rolling over a distribution made on December 31, 2010).
Note that:
 Roth conversions are usually accomplished by transferring sums directly from a
traditional plan or IRA into a Roth IRA. If both accounts are with the same
administrator or IRA provider, the traditional plan distribution and the Roth IRA
contribution would normally occur simultaneously. The 60-day deadline is
irrelevant for direct transfers (see A)).
 The IRS can extend the 60-day rollover deadline in cases of hardship. Se
To date there is no published ruling in which this provision has been used to allow
a longer period to complete a Roth IRA conversion.
 If a 2009 distribution is contributed to a Roth IRA in 2010 (within the applicable
deadline for completing an indirect rollover) that is still considered a 2009
conversion for purposes of the eligibility tests D), (E)). Reg.
A-2(a).
5.6.06 Recharacterization deadline: Due date “including extensions”
Generally, the deadline for recharacterizing an IRA contribution is the due date of the tax
return for the applicable year including extensions of time. So:
1. A regular contribution to either a Roth IRA or a traditional IRA for a particular
year, that was made by the unextended due date of the return for that year, can be recharacterized
by the extended due date of the return for that year.
2. A conversion contribution to a Roth IRA may be recharacterized by the extended due date
of the return for the taxable year in which the distribution that was converted to a Roth was
distributed (which may not be the year the distribution was contributed to a Roth IRA; see
B)), and not the year the recharacterization occurred.
“Due date including extensions” or “extended due date” has a special meaning under IRS
regulations. The taxpayer does not actually have to get an extension of his income tax return in
order to go beyond April 15 for his recharacterization decision. Reg. provides an
automatic six-months extension (from the unextended due date of the return) for all “regulatory or
statutory elections whose due dates are the...due date of the return including extensions provided
the taxpayer timely filed its return for the year the election should have been made and the taxpayer
takes” necessary corrective actions (such as filing an amended return if necessary). Emphasis
added.
What’s confusing is that there are two different “automatic” six-month extensions, neither
of which is totally automatic. Any taxpayer can obtain a “automatic” six months’ extension of time
to file his income tax return (i.e., to October 15 instead of April 15)—but it’s not truly automatic
because to get this extension the taxpayer has to request it by April 15th, usually by filing Form
4868. Reg.