Articles Posted in Otto Bosch

If you understand what an IRS Revenue Agent does on paper, you understand half of an examination. The other half — the half that determines outcomes — is how they think. The mental model an agent brings to a case shapes which issues get developed, which positions get pushed, which compromises get accepted, and ultimately…

When the IRS opens an examination of your return, the first practical question is who you should hire to defend it. Most taxpayers default to their CPA — and for many routine examinations, that is the right call. Some hire a tax attorney. A few hire an Enrolled Agent. And a small number ask the…

For years, cryptocurrency holders operated on the assumption that the IRS could not see what was happening on the blockchain. That assumption was always wrong, and it is now demonstrably wrong. Through John Doe summonses served on major exchanges, sophisticated blockchain analytics partnerships, expanded reporting requirements, and a coordinated enforcement initiative that began with Operation…

Kugelman Law attorney Otto Bosch was quoted in a Tax Notes article published May 26, 2026 — “More Scrutiny of Deferred Legal Fee Structures Could Be Coming” by Lauren Loricchio — providing the insider perspective on why the gap between an IRS audit campaign announcement and active enforcement is routine, what is happening inside IRS…

If you have received an IRS audit notice — or you are worried one might be coming — one of the first questions worth answering is who, exactly, will be examining your return. The answer matters more than most taxpayers realize. The IRS is not a single, undifferentiated organization. Examinations are conducted by specific employees…

Most taxpayers who receive an IRS audit notice make the same first call: their CPA. A few call a tax attorney. Almost none think to ask a more useful question — does the firm I’m hiring have anyone on the team who has actually sat on the other side of the audit table? A former…