The two years start on the first day an employer contribution was deposited to your SIMPLE IRA, not the day you were hired.
Count any IRA-to-IRA rollover where the money was paid to you, from any of your IRAs, including Roth, SEP and SIMPLE IRAs. Direct transfers and Roth conversions don't count.
Required minimum distributions can never be rolled over.
What kind of move this is
Watch out for
This tool is for educational and informational purposes only. It is not tax, legal, or financial advice and does not create an advisor-client relationship. Always consult appropriate professionals regarding your specific situation. It follows the IRS rollover chart and Publication 590-A. Whether a plan accepts incoming rollovers, or allows a distribution at all, depends on the plan's own rules.
Rollover or Transfer: Why the Label Matters
Moving money between two IRAs of the same type, institution to institution, is a trustee-to-trustee transfer. It isn't reported to the IRS and you can do as many as you like. When the money is paid to you and you redeposit it within 60 days, that's a rollover, and rollovers come with deadlines, withholding and limits. The difference is covered in Rollover vs. Transfer.
How the One-Rollover-Per-Year Rule Works
You can do only one 60-day rollover from an IRA to an IRA in any 12-month period, and the IRS counts all of your IRAs together: traditional, Roth, SEP and SIMPLE. The 12 months start on the day you received the earlier distribution. Direct transfers, Roth conversions and rollovers to or from employer plans don't count. A second IRA-to-IRA rollover inside the window is treated as a taxable distribution, and if you deposit it anyway it can become an excess contribution.
The 60-Day Deadline
When money is paid to you, the 60 days start the day you receive it. Miss it and the distribution is taxable, with a possible 10% early withdrawal penalty if you're under 59½. There are limited ways back, including self-certification for specific reasons. See why the 60-day rule is almost never worth the risk and why a missed deadline is hard to fix.
The SIMPLE IRA Two-Year Rule
For the first two years after your employer's first contribution, SIMPLE IRA money can move only to another SIMPLE IRA. Taking it out in that window can cost a 25% additional tax instead of the usual 10%. More in The SIMPLE IRA Two-Year Rule.
Moving Money From an Employer Plan
A direct rollover from a 401(k), 403(b) or governmental 457(b) has no withholding. If the plan pays you instead, it must withhold 20%, and you have to replace that 20% from other money to roll over the full amount. The Rollover IRA guide walks through the full process.
Sources: IRS Rollover Chart; IRS Publication 590-A, Contributions to Individual Retirement Arrangements (IRAs); IRS guidance on rollovers of retirement plan and IRA distributions.