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But if you can provide the documentation they are legally required to ask for and have a legal right to see, then a settlement is a straight-forward matter (even if the docs run to 236 pages, as they did in my 2004 tussle with them).

So my advice is this. Don't be belligerent. Ask what they need to see and then provide it. If a person is filing an honest return, he/she will be dealt with fairly and doesn't need a lawyer, accountant, etc. Their published rules can be deciphered and followed by "ordinary citizens". All that is required is patience, common sense, and honesty.

Your settlements appear to have been agreement upon and payment of the amount owed. What the OP is asking about is an "offer in compromise," where both the IRS and the taxpayer agree that the taxpayer owes more that the taxpayer can (or possibly wants to) pay, since the OP said A friend is going back six years to file taxes from 2005-2010 and is going to owe a lot of money. Can he say to the IRS, I owe you $20K, will you accept $12K or something like that?

As already advised, an offer in compromise is not something that should be attempted without prfessional advice. If the taxpayer was willing/able to pay what both the taxpayer and the IRS agreed is owed, then your approach would be more appropriate.

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