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#compliance

Compliance

Navigate regulatory compliance and maintain audit-ready financial records

Form 8300: Reporting Cash Transactions Over $10,000 for Car Dealers, Jewelers, Real Estate, and Attorneys

Form 8300 requires businesses to report cash payments over $10,000 within 15 days. This guide covers who must file, what counts as cash (including cashier's checks under $10,000), the 24-hour and 12-month aggregation rules, structuring penalties up to $31,000 per form, and the industry traps that hit car dealers, jewelers, real estate operators, and attorneys.

Form 8858 for Foreign Disregarded Entities and Foreign Branches: A Practical Filing Guide for Expat Founders, Multinationals, and U.S. LLC Owners Abroad

Form 8858 reports foreign disregarded entities and foreign branches on a U.S. return, and missing one carries a $10,000 penalty per entity per year that can snowball to $50,000 after IRS notice. This guide covers who must file, Schedules C through M, Section 987 currency calculations, the Schedule K-2/K-3 box 11 connection for Category 6 filers, and the four paths back into compliance.

Section 367 Outbound Transfer Rules: The Hidden Tax Trap When U.S. Companies Move Stock, IP, or Operations Abroad

Section 367 overrides corporate non-recognition rules the moment U.S. property crosses into a foreign corporation, forcing immediate gain on outbound asset and IP transfers. This guide explains Sections 367(a), (b), (d), and (e), the GRA and Form 8838 deferral path, the 10% Form 926 penalty, the TCJA expansion to goodwill and workforce in place, and the 2024 final regulations on IP repatriation.

Section 409A: Structuring Bonuses, Severance, and Phantom Equity to Avoid the 20% Penalty

Section 409A taxes noncompliant deferred compensation in the year of vesting and adds a flat 20% federal penalty plus interest. This guide explains the short-term deferral and separation pay exceptions, the six recognized payout triggers, the six-month delay for specified employees, and how to structure bonuses, severance, RSUs, phantom stock, and discounted stock options so founders avoid the penalty.

Section 7345 and the CP508C: How the IRS Can Revoke Your Passport and How to Get It Back

Section 7345 lets the IRS certify a "seriously delinquent" tax debt — roughly $66,000 in 2026 — to the State Department, which can deny, refuse to renew, or revoke a U.S. passport. This guide explains how the CP508C notice works, the five practical paths to decertification, the expedited procedures for imminent travel, and what the courts have recently said.

Section 7701(b) Substantial Presence Test for Foreign Entrepreneurs: The 183-Day Formula, Closer Connection, and Treaty Tie-Breakers

A practical walkthrough of IRC Section 7701(b) for globally mobile founders — the 31-day floor, the weighted three-year 183-day formula, exempt-individual rules, the closer connection exception (Form 8840), and treaty tie-breakers (Form 8833) — with a worked example showing how 130 U.S. days in 2026 can trigger worldwide taxation.