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As long as it is not covering the same expense twice it should be fine. In other words, I have a medical bill for $10,000. I believe that I have $5,000 available elsewhere so I take a $5,000 hardship to cover the balance. I end up not being able to pay the other $5,000 so I need another hardship. As long as the combined hardship withdrawals do not exceed the documented expense it shouldn't be a problem.

I've been gone for a few years....due to typical life distractions. My posts aim towards investment questions, trying to simplify some issues for common layperson situations, and suggesting some of the minefields to avoid. To all the general readers of this message board. If you have a IRA, Roth or any other account with designated beneficiaries you should get into the practice one a year to confirm that your wishes are recorded for first and second choice beneficiaries. It takes maybe 3 minutes online to check. Do it at year end, when you start your taxes, of on your birthday. Do it every year because as accounting system software gets changed, financial firms merge, and accounts get moved the custodial designation can get lost in the shuffle. Even more important, as years pass, family structures change. Tip: You might be able to build in a "toggle" to each account which may allow a surviving spouse to make a decision on death how assets should pass. For example: spouse if primary beneficiary and three children are equal secondary beneficiaries. Upon your death, wife has the option to accept all or part of the assets. Any assets not claimed would be distributed to the children. Example: Wife started a Roth long ago, invested wisely, and now has a million dollar account. Husband is the primary, three children are equal secondary beneficiaries. Upon her death, the husband as primary beneficiary accepts $400,000 but declines to take the 600K. Those funds now pass to three children as 200K each. This might be used as an inheritance planning tool. Remember - check those beneficiary designations !

We have layperson readers of this message board. Let me try to clarify some points. IF you do a direct custodian movement of funds, such as IRA to IRA, or Roth to Roth, and you never touch the funds, you have no restrictions. Example 1: Custodian for account A can send money to B and C. Example 2: Custodian A can send funds to B, and separately Custodian C can send funds to D. These are the most common type of movement of funds from one custodial IRA/Roth to another, the one per year does not apply. If you don't touch the funds, then the one and done restriction does not apply. IF you have the funds sent to you. Then you have a 60 day window to redeposit funds into the same IRA or a different IRA of the same class. IF you are moving from IRA to Roth, then you fall under the conversion rules. This is not a rollover or distribution but a conversion. This somewhat oversimplifies the rules, but probably covers 90% of the common transactions.

I would argue that the computation period is not over (and the EE has not accrued a YOS) until the last day in the period is over. Entry 1/1/2019.