01The 60-day rule, precisely
When you take possession of retirement money — a check made out to you, a transfer into your checking account — the distribution is provisionally yours, and the IRS gives you 60 calendar days from receipt to put it into an eligible retirement account. Make it and nothing is taxed; the rollover is reported and ignored. Miss it and the entire amount is ordinary income for the year, with a 10% early-distribution penalty stacked on top if you're under 59½.
If you haven't taken the check yet: don't. Ask both custodians for a direct trustee-to-trustee transfer — the money never touches your hands, no 60-day clock ever starts, none of the traps on this page apply, and you can do it as many times as you like.
02The 20% withholding trap
03The once-a-year rule (IRA only)
Indirect IRA-to-IRA rollovers carry a second limit that has nothing to do with speed: one per rolling 12 months, counted across every IRA you own — traditional and Roth together. The tax court settled this in 2014, and there is no fix after the fact; a second indirect rollover inside the window is simply a taxable distribution, even if you redeposit the money the same afternoon. The rule does not apply to direct trustee-to-trustee transfers, to rollovers between a workplace plan and an IRA in either direction, or to Roth conversions. If you find yourself doing indirect rollovers often enough to track this rule, switch to direct transfers and stop needing to.
04Missed it? Self-certification first
A blown deadline used to require a private letter ruling — months of waiting and a five-figure IRS fee. Since 2016 there's a self-service path: if you missed the 60 days for one of 12 enumerated reasons (custodian error, lost check, illness, family death, disaster, incarceration, and others), you write a one-page letter following the IRS model text in Rev. Proc. 2020-46, hand it to the receiving custodian, and complete the deposit as soon as practicable — within 30 days of the reason resolving is the safe harbor. No fee, no pre-approval; the IRS can check the claim on audit, so the reason has to be true.
More money-deadline tools: GraceWindow (your CD's exit window), ZeroEnds (your 0% APR cliff), LateMark (the 30-day late line) — all tools.