Simplifying SIMPLE IRA Rollovers
You should be able to transfer money directly from one employer's retirement savings account to another.
I have a SIMPLE IRA account at New York Life through my last employer. I recently decided that I want to roll over the contributions to my current employer's 401(k), which is managed by Fidelity. As per my understanding, this can be done by asking New York Life to write a check to Fidelity. But New York Life will only make a check payable to me. But if New York Life does this, I understand that I would have to go through an extra step of proving to the IRS that I rolled over the amount, so I will not have to pay a penalty. I do not understand why New York Life will not just make the transfer directly to my 401(k) with Fidelity.
We contacted New York Life, which tracked down the tape of your phone call to customer service (always wondered what happens when they say, "the call is being recorded"). After reviewing the records, it's easy to see how the answer could be confusing. But the good news is yes, you can have the money transferred directly from your SIMPLE IRA to your new 401(k).
The rules for SIMPLE IRA to 401(k) transfers are a bit different from what they are when transferring money from one 401(k) to another. Sam Mancino, managing director of New York Life Retirement Plan Services, says that to make the direct transfer, you need to be in the SIMPLE IRA for at least two years from your first contribution (which you've already done), provide a letter of instruction to New York Life with a medallion signature guarantee if the transfer is more than $50,000, and provide a letter of acceptance from your new plan sponsor stating that the plan will accept your rollover.
Mancino says your first step should be to contact customer service at New York Life and ask for a SIMPLE IRA distribution form, which you'll give to your current employer to fill out with information about your new account. Also ask your employer for a letter of acceptance telling New York Life that the plan will accept the rollover contribution. Then send New York Life that information and a letter of instruction asking specifically to have the check made out to your new 401(k) account at Fidelity, not to you personally. That way, you won't need to worry about any tax consequences.
Those tax consequences, however, are much less complicated because your current account is a SIMPLE IRA rather than a 401(k), says Mancino.
When you roll over money from one 401(k) to another, you could have it transferred directly to your new account or have the check written out to you. As long as you deposit the money in the new 401(k) within 60 days, you won't be hit with a penalty or tax bill. But 401(k) administrators will withhold 20% in taxes on that money, and you must make up that difference with money from outside of the account or end up with an early-withdrawal penalty. You won't get the withheld money back until you file your taxes. Mancino says that with a SIMPLE IRA, on the other hand, the administrator doesn't have to withhold taxes from the check, even if it's made out to you.