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Say I am employed with company 'A' with whom I have a 401K account. Now, while switching jobs, I decide not to carry forward this 401K to the next employer but instead rollover this 401K I had with company 'A' into a rollover IRA, which I later convert to a Roth IRA.

Now, say I am with my new employer 'B'. When I switch my job again, can I once again rollover this 401K (I have with employer 'B') into the my rollover IRA account and later convert it to Roth IRA?

This process is more like a backdoor to having an IRA account if your income is above the state specified limits. Therefore, if such multiple rollovers are possible, how many such rollovers are allowed?

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    Just be aware that even if you have a Roth 401(k) only -- which can be rolled over tax-free into a Roth IRA -- your employer match (if any) is in a pre-tax account and will be rolled over into a Traditional IRA. Oct 28, 2021 at 15:30

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I do not believe there is any real limitation. This IRS web page is instructive.

Note that the limit of one rollover per year appears to apply when you have received a distribution from another IRA and want to put it into another IRA.

Note:

The one-per year limit does not apply to:

  • rollovers from traditional IRAs to Roth IRAs (conversions)
  • trustee-to-trustee transfers to another IRA
  • IRA-to-plan rollovers
  • plan-to-IRA rollovers
  • plan-to-plan rollovers

where I've bolded the items that seem to apply in your case.

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    Note that you still need to pay income tax on a Traditional-to-Roth conversion, and it counts as regular income, which may push you into a higher tax bracket.
    – D Stanley
    Oct 28, 2021 at 15:57
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    It seems clear that this question is talking about rollovers from 401(k)s into IRAs (which are plan-to-IRA rollovers). So the first two items in the list (the ones you've bolded) definitely don't seem to apply in this case, but the fourth item does apply. Oct 28, 2021 at 16:08
  • @TannerSwett D'oh! You're right. Will update. Thanks!
    – Peter K.
    Oct 28, 2021 at 16:51

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