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I would do them separately. Why would you include a timely filing with a late filing. Perhaps you extend 2023 and file it in October. But go ahead and submit the two late ones as soon as you can. https://www.irs.gov/retirement-plans/penalty-relief-program-for-form-5500-ez-late-filers

https://www.irs.gov/retirement-plans/simple-ira-plan-fix-it-guide-your-business-sponsors-another-qualified-plan I believe you are correct unless you want to try to go through VCP for the SIMPLE IRA since it's the SIMPLE-IRA that has problems if you also maintain a qualified retirement plan in the same year. There might be some threads here on benefits link if you do a search, I think this has come up a few times in threads.

If the independent qualified public accountants delivered an “unmodified” report the IQPA authorizes the plan’s administrator to upload in the Form 5500 report, that the administrator received a management-weaknesses letter (see below) is not itself a distinct disclosure item in Form 5500. What is a management-weaknesses letter? Under certified public accountants’ professional standards, an auditor must communicate to “management”—for an ERISA-governed employee-benefit plan, the plan’s administrator—about “significant deficiencies” and “material weaknesses” in the plan’s internal control. (Internal control is auditor-speak for ways of making sure you do things correctly, and ways of preventing, or at least detecting, what someone does wrong.) If the accountants during their audit of a plan’s financial statements found an internal-control problem, the firm typically sends a “management weaknesses” letter. The letter usually includes at least the deficiencies and weaknesses the CPAs’ professional standards require them to tell you about. Also, the rules permit an auditor to tell “management” about other control-related matters. Why you should read the management-weaknesses letter Instead of just filing away the letter, read it. First, receiving information and failing to consider it likely is a breach of a fiduciary’s duty of care. And one might as well use something the retirement plan or its sponsor already has paid for. Look for a “false positive” When you read the auditor’s letter, use some prudent skepticism yourself. Even a careful auditor obtains only an incomplete, and sometimes incorrect, understanding of a plan’s provisions and operations. A finding about a deficiency or weakness might be wrong. If you have even a slight doubt about a finding, check the source documents and records yourself, or get a careful worker to test the auditor’s finding. If you see a mistake, don’t ignore it. Instead, write an explanation of your plan’s procedure for the task involved. Or if the mistake is that your auditor’s finding is that you lack a control that’s unnecessary for your plan, write a cogent explanation about why the control is unnecessary. Respond to every mistake; doing so can help avoid wasted time and effort in the next audit. Look for procedures that need improvement On some points, you might concur with your auditor’s finding that a procedure or control could be tighter. If so, start work on the needed improvements. Aim not only to design but also to implement the improvements before the next audit engagement begins. (Many auditors use the preceding years’ management-weaknesses letters, and a client’s responses to them, as tools to help evaluate risks the auditor must consider in planning an audit.) But if making a new procedure or control would require the retirement plan to incur an expense, you must as a prudent fiduciary evaluate whether the value of the improvement makes the expense worthwhile. Get help from your advisers A plan’s administrator might ask its lawyer for advice about the management-weaknesses letter and how the administrator should act on the information. After considering the lawyer’s advice, an administrator might consider sharing the auditor’s letter with its third-party administrator, recordkeeper, and other service providers. They might suggest ways to improve the plan’s procedures. A TPA’s or recordkeeper’s way to fix a problem might be more efficient than a method the employer/administrator alone would have found. Using good sense Even if a list of problems feels unwelcome, an employer/administrator can evaluate and act on an auditor’s management-weaknesses letter to keep making improvements in how one administers the retirement plan. This is only general information, and is not advice to anyone.

@Mark G if you follow your proposed strategy, and the proceeds from the sale of the old car are less than the price pay for the new car, then the net result of the strategy is a taxable withdrawal from the IRA. For example, assume you have $500,000 in your IRA and take a distribution of $50,000 to buy the new car. You now have $450,000 left in the IRA. You sell the old car for $20,000 and deposit the $20,000 in cash into the IRA within 60 days as a rollover. You now have $470,000 in the IRA and a net taxable distribution of $30,000. Do you happen to be taking Social Security payments and not have other taxable income that triggers paying taxes on the Social Security payments? If so, then the taxable distribution could trigger needing to pay taxes on the Social Security payments. You do not mention what your rate of return is within the IRA. If your rate of return within the IRA (adjusted for your marginal tax rate you would pay on a withdrawal) is greater than the interest rate you will pay on a car loan, then you are better off taking out the car loan and making the payments over time from your IRA distributions. If you or your spouse are still working, you have the option to contribute funds received from the sale of the old car. If you do this, then consider making the contributions to a Roth IRA to keep the contribution and future income from being taxable later (after 5 years) and from being included in the calculation of your required minimum distributions when you reach age 73. There a lot of variables and assumptions that go into comparing the different strategies. There are no guarantees that all of your assumptions will accurate, and some strategies will carry a higher risk of unintentionally creating unwanted tax consequences. If you are adamant about taking the DIY approach, get the best information you can about the price you will pay for the new car, the proceeds you can reasonably expect from the sale of the old car, the likely terms of taking a car loan, any of your and your spouse's expected earnings from employment, a reasonable estimate of the investment performance of your IRA over the next 5 to 7 years, your marginal tax rates, start dates and amounts of any Social Security payments to you and your spouse, and any other factors. Write them all down, and do the math. If you think you are good to go, then ask someone you know and trust or ask a professional who is financially savvy to review your work and help you assess the risks. May you find a clear path forward.

I agree, no controlled group. No attribution because neither the parent nor the child owns more than 50%. IRC 1563(e)(6)(B) Jak, the issue you're thinking of has to do with controlled groups that are formed between spouses (or unmarried parents, for that matter) who are both owners of their own businesses when they have a young child together. The 1563(e) rules automatically attribute ownership from a parent to a minor child, so a controlled group would always exist because the child would be attributed all of the parents' ownership and therefore the child would be deemed to own 100% of both companies. SECURE 2 didn't change 1563, but it changed 414(b), (c), and (m) to say that a controlled group or affiliated service group will not be considered to exist merely because of the existence of a minor child, or because the spouses live in a community property state.

Just file the amended 5500 ASAP attaching the auditor's report. From Form 5500 instruction – “If the required IQPA’s report is not attached to the Form 5500, the filing is subject to rejection as incomplete and penalties may be assessed.“ From DOL EFAST FAQ – “Q25: Will EFAST2 receive my filing if I do not attach the IQPA report to my Form 5500 annual return/report? EFAST2 will receive your filing, but the filing is incomplete without the required IQPA report. An incomplete filing may be subject to further review, correspondence, rejection, and civil penalties. Please note Schedule H, line 3 specifically asks for information regarding the plan’s IQPA report. If you do not submit the required IQPA report, you must still correctly answer these questions. If you have to file Form 5500 without the required IQPA report, correct that error as soon as possible.”

Here's the wording on our document, FWIW... The following are optional administrative provisions. The Administrator may implement procedures that override any elections in this Section without a formal Plan amendment. In addition, modifications to these procedures will not affect an Employer's reliance on the Plan.

Many pre-approved documents (which is about all I see these days) have a specific Administrative Procedures addendum that specifically deals with questions like this - Relius does, for example. Take heed of Bri's comment.

I recommend speaking with your CPA or financial planner.

Verily, and with great haste, thou shalt consulteth thy plan's governing documents and discover therein the answers thou seekest. Should fortune smile upon thee, thou may findest that thy plan be graced with a determination letter, be it sealed by the hand of the wise ones who dwell within the halls of the Internal Revenue Service, granting reliance upon the terms found therein. In that happy moment, thou shalt knowest that thy plan's allowances of in-service distribution of rollover accounts shall never be said to fail to satisfy the requirements of section 401.

Once money is rolled into the plan, it’s rollover money and it doesn’t matter what it was in the other plan. Our plans (almost) always allow participants to take a distribution of rollover money at any time. Read the document and it will tell you.

EBECatty explains the frame of removing Chevron deference. To start with two examples of how someone might like to interpret a statute differently than the agency does: ERISA § 3(21)(A)(ii) makes a person a plan’s fiduciary “to the extent he renders investment advice for a fee or other compensation, direct or indirect, with respect to any moneys or other property of such plan, or has any authority or responsibility to do so[.]” In a dispute, one may seek to persuade the court about the meaning of the quoted phrase and how that meaning applies to the facts and circumstances of the dispute. The arguments could go in either direction; for example, that an insurance producer’s recommendation is not advice, or that even a communication the Labor department’s rule describes as not advice is investment advice. Interpreting ERISA § 104(b), one might reason that the ways to “furnish” a summary plan description or other disclosure are wider than those recognized in the Labor department’s rule.

I have not given this a great deal of thought, but as Peter notes, won't the impact be limited to agency interpretations/guidance that the agency feels complies with the statute but that a federal court does not (and previously may have been compelled to defer despite its disagreement)? Eliminating Chevron does not mean the agency no longer has authority to write rules; it just means (in my understanding) that a federal court is no longer required to defer to the agency's interpretation if the court thinks a better interpretation is available under the statute. In other words, you would have to find a regulation not only that you dislike, but one that also is so at odds with the underlying statute that a federal judge would change the rule. The judge might still be persuaded that the agency's rule is correct. That said, I would be interested to hear of good examples where this could change the outcome. Also, EPCRS is authorized by statute (29 USC 1202a): (a) In general The Secretary of the Treasury shall have full authority to establish and implement the Employee Plans Compliance Resolution System (or any successor program) and any other employee plans correction policies, including the authority to waive income, excise, or other taxes to ensure that any tax, penalty, or sanction is not excessive and bears a reasonable relationship to the nature, extent, and severity of the failure.

That sounds appropriate, but really comes down to the Plan Administrator interpreting the document and its standard operating procedures conforming to Its interpretation. So if the bonus were a separate paycheck, he'd have gotten $200 total that week, I suppose.

Without knowing the facts - and the many variations they could take - this recent IRS GLAM provides some discussion of related topics from a compensation standpoint (assuming there is some compensatory aspect here). Not sure how close your situation is to the facts in the GLAM, or whether the arrangement would be similar to product marketed therein, but may be worth a read: AM 2022-007 (irs.gov)