The IRS Is Watching. Is Your Return Ready? — Insights | Neil Jesani Advisors
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Tax Strategy·Q2 2026·4 min read

The IRS Is Watching. Is Your Return Ready?

Enforcement is scaling. If your income exceeds $2 million, the question is no longer whether the IRS may review your return — it’s whether you’re prepared when they do.

For years, budget constraints kept IRS audit rates near historic lows. That era is ending. With significant new funding directed toward enforcement and an explicit directive to focus on high-income filers, the agency is rebuilding its capacity to scrutinize complex returns. If you earn above $2 million annually, this is an operational concern.

The risk is not in the strategies themselves. It is in the gap between what is claimed and what can be proven.

Why aggressive positions have become higher-stakes

Tax minimization is the legitimate and appropriate goal of good planning. The problem arises when positions are taken without the documentation to defend them. The IRS does not simply accept deductions at face value. It examines whether they reflect economic reality, whether proper elections were filed, and whether the taxpayer can substantiate their claim under scrutiny.

An undocumented deduction is not just a risk on paper. It is a liability. And when income is above $2 million, the dollar exposure from a single disallowed position can be material.

The three audit triggers that matter most

Certain areas of the return draw disproportionate attention. These are not obscure edge cases — they are commonly used planning strategies that the IRS has specifically flagged for review.

Audit TriggerWhat the IRS looks for
Home Office DeductionExclusive, regular business use — requires concurrent records and a clear physical demarcation of the space
Real Estate Professional Status (REPS)750+ hours in real estate activities, material participation logs kept contemporaneously — not reconstructed after the fact
Large Charitable DeductionsQualified appraisals for non-cash contributions must be completed before filing — a missing or late appraisal disqualifies the deduction entirely

Real Estate Professional Status in particular has become a focal point. The ability to deduct rental losses against ordinary income is a powerful benefit. But it requires that the taxpayer spend more than 750 hours per year in real estate activities, and that this time be carefully documented. Missing logs, approximate estimates, or retroactively constructed timesheets will not survive examination.

The answer is documentation, not overpaying

None of this means high-income individuals should abandon tax strategies. It means those strategies must be built on a foundation that holds.

The distinction between a defensible position and a vulnerable one is rarely about the underlying law. It is about execution. Was the election filed? Are the hours logged contemporaneously? Does the appraisal meet IRS requirements? Is there a clear paper trail connecting the deduction to its business purpose?

The best tax plan is one that saves you money and survives a letter from the IRS. In most cases, those two goals are completely compatible — if the plan is built correctly.

High earners who work with advisors that treat documentation as an afterthought are carrying more risk than they realize. The return that looks aggressive but is carefully supported is far less exposed than the return that looks modest but cannot be explained under questioning.

The IRS is not simply looking for fraud, but for positions that lack substance, elections that were never properly made, and deductions that cannot be reconstructed from records.

These are not rare and peculiar situations, and instead very commonplace problems. However, they are not reasons to pay more in taxes. They are reasons to make sure every dollar saved is a dollar you can keep.

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