The Seven Markers

Nearly every structure the government has successfully attacked shares the same handful of features. Once you know what they are, you can screen a pitch in about ten minutes.

Score a proposed structure against these. Every structure the government has successfully attacked shares most of them. Three or more is a stop.

1.A promised deduction or savings multiple
'4-to-1.' '5-to-1.' 'Shelter 98% of your profits.' Real tax planning produces a deduction equal to what you actually spent or actually gave away. A promised ratio is the single most reliable tell.
2.The promoter selects the appraiser or the actuary
In every valuation case the government has won, this is the fingerprint. If you did not choose the valuation professional and cannot fire them, the valuation is not independent.
3.Fees consume most of the capital
One publicly documented technology-donation offering allocated 25% to purchasing the asset, 62% to legal, accounting, management and audit-defense fees, and 13% to broker commissions. Roughly one dollar in four reached the thing being donated. That is not an investment.
4.Contingent or percentage-of-savings fees on an original return position
Also a Circular 230 Sec. 10.27 problem for the CPA, and an independent disqualifier of any opinion under IRC Sec. 6664(d)(4)(B)(ii)(III).
5.The client keeps control of what they supposedly gave away
Charitable LLCs, 643(b) spendthrift trusts, deferred sales trusts, sham management companies. Same defect every time: dominion and control never actually left.
6.The economics do not work without the tax benefit
This is literally the IRC Sec. 7701(o) test. It carries a 40% strict-liability penalty under Sec. 6662(i) with NO reasonable cause defense of any kind under Sec. 6664(c)(2). No opinion letter, however independent or expensive, reduces it.
7.'The IRS has never listed this'
Absence of a designation is not approval. Patel, Avrahami, and the charitable LLC FSA were all decided on general doctrine, not on reportability. Every promoter said this before the notice issued.

No markers triggered

0 of 7 triggered|weighted 0

You may be looking at real planning. It still needs to be executed properly, documented contemporaneously, and reviewed by someone whose compensation does not depend on your saying yes.

Every marker here traces to a structure in the library. The scoring runs entirely in your browser and nothing is transmitted or stored.

Supplemental tells

Not scored, but each one should raise the temperature of the conversation.

The pitch leads with the deduction rather than the underlying business or risk
A confidentiality or non-disclosure agreement covering the structure itself
The promoter supplies the 'documentation kit' or the meeting minutes template
Audit defense is bundled into the fee, which prices in the expectation of audit
You are told your own CPA 'will not understand this' or 'is too conservative'
The opinion letter comes from counsel the promoter introduced or pays

One question worth asking out loud

“How are you paid on this?” A good advisor answers immediately and specifically. If the person recommending a structure is compensated by placing it, you are not receiving advice. You are receiving a sales presentation delivered by someone with a professional credential.