By: Steven D. Hamilton, Principal, Steven D. Hamilton, CPA

March 15, 2015 9:07 pm EDT

I have come to the conclusion that I do not like for folks to receive a check when they do an IRA rollover.

What are we talking about?

Say that you have an IRA at Fidelity and you want to transfer it to Vanguard. Another example is that you have a 401(k) with a previous employer, and you have decided to move out of the 401(k). In each case you are transferring money into an IRA, whether from another IRA or from an employer plan.  

There are two ways to do this:

(1)  Instruct Fidelity to send the monies directly to Vanguard. This is sometime referred to as a “trustee-to-trustee” or a “direct” rollover. Notice that you ever see the money, although you may feel the breeze as it rushes by.

(2)  Instruct Fidelity to send you a check and then you in turn will send the money to Vanguard.

Option two is fraught with danger, beginning with convincing Fidelity not to withhold taxes. They do not “know” that you are actually rolling the monies, and they do not want to be holding the bag if the IRS comes looking. If they withhold $1,000, as an example, you are going to have to reach into your wallet to transfer the full amount to Vanguard. Otherwise you will be $1,000 short, meaning that $1,000 will be taxable to you when it is time to file your taxes.

An equal or bigger danger is that the IRS allows you only 60 days to send that check on to Vanguard. Miss that deadline and the IRS will say that you flubbed the rollover, taxes (and perhaps penalties) are due and thanks for playing.

How do you get out of it? Well, you are going to have to formally ask the IRS for a waiver, and wait on the IRS to give it. This process is referred to as a “private letter ruling.” The IRS is issuing a ruling to you, and it is to you and you only (that is, “private.”)

Is expensive? It can be, not the least for a CPA’s time in drafting the thing. Depending upon the issue, the IRS might also charge you money, and that cost can go into the thousands.

How can you miss the 60 days? There seems to be an endless variety. One can get sick, have family emergencies, the financial institution can make a mistake. I have lost track of how many of these I have read over the years.

And now I am reading another. Let’s talk about it, as I can see this story sneaking up one someone.

The taxpayer – by the way, taxpayers in private letter rulings are anonymous. We need to give “anonymous” a name for this discussion, so we will call him Sam.

Anyway, Sam wants to move his IRA. He meets with an advisor, who cautions him that the “new” IRA trustee will charge for rolling the IRA. Sam would be much better off having the old trustee reduce everything to cash, and then sending the cash to the new trustee.

OBSERVATION: While the PLR does not dwell on it, there obviously are some difficult-to-sell assets in Sam’s IRA. It does not have to be anything esoteric – like platinum-plated gold from the moon. It could be something as simple as a non-traded REIT.

Sam contacts a representative of the old trustee and explains that he is rolling over his IRA.  He has opted to pursue option (2) above, and would they be so kind as to help him with the process. Not a problem, they say, although it might take a few months to reduce the IRA to cash.

And there is the first big red flag.

 Sure enough, old trustee sends Sam checks – plural. Six checks in total, over a period of more than 60 days.

Second red flag.

Sam was clever though. Sam did not cash any of the checks, figuring that if he did not cash the check then the 60-day period did not start.

Sam finally sends all the checks over to new trustee, who realizes that there is a problem. What problem? The problem that the 60-day period does not work the way Sam thought.

New trustee contacts old trustee and requests that they issue a stop payment on the checks.

Good job.

You see, the stop payment means that the checks could not be cashed, rendering them not much of a check at all. Since they could not be cashed, the monies could never leave Sam’s old IRA, and the issue of a rollover becomes null and void.

There is one more step: getting the IRS to agree with the above line of reasoning.

Which Sam did with his private letter ruling (PLR).

And I suspect that the professional and filing fees for the PLR may approximate what the new trustee was going to charge for handling the transfer in the first place.

By the way, do you know how this should have been handled? By instructing the old trustee not to send a check until everything has been reduced to cash, and then to send one and only one check for the entirety of the account.

I know that, and you know that. But somewhere sometime someone will repeat this story. Which brings me to the conclusion that people should not do option (2) rollovers unless there is no other alternative.

It just isn’t worth the risk.

IRA rollover401(k)
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