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Assuming you have the rollover account set up and ready to receive the funds from the 401(k), the check should be made out to the IRA custodian i.e., say Schwab, Fidelity Investments or another investment manager for the benefit of you. In this case, there is no tax withholding.
If you miss the 60 day window, the check becomes taxable income, like any other withdrawal. You will receive a 1099-R in January 2023, and you report the withdrawal on your 2022 tax return. You will pay regular income tax plus a 10% penalty if you are under age 59-1/2.
Please note: When a rollover check is made payable directly to you, you must deposit the money into your IRA within 60 days of receiving the check to avoid income taxes and a possible early withdrawal penalty.
Rollovers typically take 2-4 weeks to complete.
IMPORTANT: The IRA Rollover Request Form is used to initiate a rollover of assets to a qualified retirement plan. This form authorizes Retirement Clearinghouse to request a transfer of assets on your behalf.
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A rollover may entail a number of actions but often refers to the transfer of the holdings of one retirement plan to another without having to pay taxes. When a rollover occurs it may mean a person has reinvested funds from a mature security into a new issue of the same or similar security.
Most pre-retirement payments you receive from a retirement plan or IRA can be rolled over by depositing the payment in another retirement plan or IRA within 60 days. You can also have your financial institution or plan directly transfer the payment to another plan or IRA.
Rollovers typically take 2-4 weeks to complete.
It is a process that allows you to move funds from your previous employer-sponsored retirement plan, a 401(k), for example, into an IRA.
To initiate the rollover, you complete the forms required by both the IRA provider you choose and your 401(k) plan administrator. The money is moved directly, either electronically or by check. No taxes are due on the assets you move, and any new earnings accumulate tax deferred.

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