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I'd be careful with terminology. Unless this TPA is taking on the role of a plan fiduciary in some capacity, the TPA doesn't "approve" distributions. A TPA would "confirm" that the requested distribution or IRR is permitted by the plan and that the participant is eligible for it. But a non-fiduciary TPA doesn't approve anything. Might seem to be a little thing, but us TPAs are obsessed with lots of little things.

Thank you Bill, that's very helpful! And yes, I contacted HR, the answer from them, it's #2. Company have the True-up contribution, it'll be calculated end of the year, and will be contributed to the account in the 1st Q of 2021. It does make me feel better now.

To help you prepare to ask your lawyer for advice (or to ask the plan’s administrator to instruct you), you might read: ERISA Advisory Opinion 2013-03A (July 3, 2013) (Principal Life Insurance Company). https://www.dol.gov/sites/dolgov/files/EBSA/about-ebsa/our-activities/resource-center/advisory-opinions/2013-03a.pdf That interpretation includes EBSA’s view that, even if an arrangement involves no set-aside, a contract right to have some amount “applied to plan expenses” could be the plan’s asset. A plan’s administrator should not rely on the investment or service provider’s description that an arrangement is not plan assets. (1) It can’t be prudent to rely on legal advice from a person that denies that it provides legal advice. (2) It is imprudent for a retirement plan’s fiduciary to rely, without further steps, on advice from a person that has an interest (other than the plan’s interest) about the subject for the advice. Further, if something is plan assets, the plan’s administrator might want its lawyer’s advice about how to allocate the plan trust’s assets. This might involve careful readings of the plan, its trust, and the plan-expenses arrangement. Not every plan-expenses arrangement has the same terms, and (even within IRS-preapproved documents) governing documents can state different provisions about how to account for and use an arrangement.

One. The forms will let you take it all the way back (i.e., check that you missed both restatements) on one submission.

This is an interesting thread. It's not really about how many plans, for the reasons mentioned - size and complexity. A different metric, not necessarily the be-all and end-all, is revenue. I think most owners feel their admins should be billing at least 2 times their salary plus benefits; some maybe 3X. I'm a lousy businessperson/owner and never really got to 2X. 300 plans with one person primarily responsible sounds pretty crazy to me. I imagine they would be totally and completely screwed if you left...