Missing 1099-R

I'm handling an IRS audit (2021) for a client.

1. How many clients keep a copy of the collective bargaining agreement?  I don't know where to tell the client to look.

2.  The non-union are all family,(four brothers and a sister); the plan excludes union employees subject to collective bargaining agreement.   One of the family members quits and receives a distribution, which he rolled over to an IRA.  Apparently no 1099R was issued

3.Despite many attempts to get a copy of the rollover check, the account value as of 12/31/202 was shown on Form 5500-SF for 2021 in order not to be a late filing. Obviously Form 5500 will need amendment.

Question - obviously no 1099-R was prepared or filed; is it even possible to file a 1099R currently for a distriubtion that occurred in a prior year?

Can a 1099-R be filed currently for a previous years' distribution?  The IRS website lists the fines for a late 1099-R-  apparently this one would only be $280, but I'm sure they will add penalties and interest?  The guy rolled over $1.5M to an IRA.

You wouldn't needa 1099R to show a distribution on the 1040, I would think that is the individuals responsibility to show as income and deduct as an expense, but that is his problem.

I’m not where I can look up a bunch of stuff, but related to item #1, I can’t imagine anyone agreeing to benefits and wages as part of a collective bargaining agreement and not knowing exactly what that agreement said and where a copy was kept. 
 

What a stupid way to run a business. 

How do you enter into a collective bargaining agreement and not keep a copy?

Yes you can file a late 1099-R, as you have discovered, penalties apply.

The participant is probably fine as the taxable amount will be $0 if it was properly rolled over. But the plan has a duty to file the 1099-R and supply to the participant. At most he'd need an amended return showing ~$1.5M distribution, but report it as non taxable rollover.

The penalty for not filing (if not done intentionally, is something like $280, which is no big deal.

The interest would be charged from 1/31/22, would the same tiered interest rates as late payment of income tax apply?  I would think so.