#tax-compliance
Tax Compliance
Stay compliant with tax regulations and filing requirements
Form 5472 for Foreign-Owned US LLCs: The $25,000 Penalty Trap That Catches Single-Member Disregarded Entities Off Guard
Foreign owners of US single-member LLCs must file Form 5472 by April 15, 2026, even with zero revenue. A capital contribution as small as $1 triggers the requirement, and a missed filing carries a $25,000 minimum penalty plus uncapped $25,000 continuation fees every 30 days after IRS notice.
Key Person Life Insurance and Section 101(j) Compliance
Key person life insurance pays the company, not the family, when a founder, rainmaker, or specialist dies. IRC Section 101(j) makes the death benefit taxable unless written notice and consent are completed before the policy issues — a step most small businesses skip, turning a $1M tax-free benefit into roughly $600K–$700K after tax.
The 1099 Threshold Just Tripled to $2,000: What Small Businesses Should Actually Do About It
The 1099-NEC and 1099-MISC reporting threshold rises from $600 to $2,000 for payments made in 2026 under the One Big Beautiful Bill Act. Backup withholding still kicks in at the same threshold, the 1099-K bar resets to $20,000 plus 200 transactions, and most states have not adopted the federal change—so vendor recordkeeping matters more, not less.
Section 45F in 2026: How OBBBA Quadrupled the Employer-Provided Child Care Credit
Starting in 2026, the One Big Beautiful Bill Act expands Section 45F's Employer-Provided Child Care Credit from 25% to 40% (50% for businesses under $32M in average gross receipts) and lifts the annual cap from $150,000 to $500,000 ($600,000 for small businesses), with new explicit rules for intermediaries, pooled arrangements, backup care, and reserved-seat contracts.
Unrelated Business Income Tax (UBIT) and Form 990-T: When Your Nonprofit's Gift Shop, Ads, or Side Ventures Trigger a 21% Tax Bill
How nonprofits trigger Unrelated Business Income Tax — a flat 21% federal levy, the three-part IRS test, traps in gift shops and advertising, statutory exclusions, and the post-2017 siloing rules under IRC §512(a)(6) that lock losses to each unrelated business.
The 1099-K Whiplash Ends: Why the $20,000 and 200-Transaction Threshold Is Back for 2026
The One Big Beautiful Bill Act repealed the $600 1099-K threshold in July 2025 and restored the original $20,000-and-200-transaction federal rule, easing paperwork for casual sellers and gig workers — but every dollar of business income remains taxable.
Form 5500-EZ Solo 401(k) Filing Threshold: When Self-Employed Plans Cross the $250,000 Asset Trigger
A Solo 401(k) crosses into mandatory Form 5500-EZ filing once combined plan assets exceed $250,000 on the last day of the plan year. Late filings cost $250 per day up to $150,000 annually, but Rev. Proc. 2015-32 caps catch-up filings at $1,500 per plan if no penalty notice has been issued.
Section 183 Hobby Loss Rule: How the IRS Nine-Factor Test Decides If Your Side Activity Is a Business
Section 183 of the Internal Revenue Code denies loss deductions for activities not engaged in for profit. The IRS applies a nine-factor test and a three-of-five-years safe harbor (two of seven for horses) to distinguish a real business from a hobby — here is what each factor weighs and how to document profit motive before an audit.
409A Valuations: A Founder's Guide to Stock Option Strike Prices and Safe Harbors
A 409A valuation is the IRS-recognized appraisal that sets the strike price on every option grant. Without one, founders risk 20% federal excise penalties, premium interest, and California's 5% piggyback tax — all falling on the employee.
Form 1042-S Withholding on Payments to Foreign Persons: A Compliance Guide for US Businesses
Form 1042-S reports US-source FDAP income paid to foreign persons. US businesses act as withholding agents with personal liability — default 30% withholding, W-8 documentation rules, March 15 deadlines, and stiff per-form penalties. This guide covers W-8BEN versus W-8BEN-E, treaty rate reductions, the source-of-income rules, and common mistakes like sending Form 1099 to a foreign contractor.
Form 7203: How S-Corp Shareholders Track Stock and Debt Basis (And Why It Matters)
Form 7203 forces S-corp shareholders to prove their stock and debt basis on Form 1040. Misapplying the ordering rules or treating loan guarantees as debt basis can disallow loss deductions, reclassify distributions as capital gains, and trigger 20% accuracy penalties.
Form 8606 and the Backdoor Roth: How One Missing Tax Form Causes Double Taxation
Form 8606 is the IRS's running ledger of after-tax basis inside traditional, SEP, and SIMPLE IRAs. Skip it and the IRS treats your basis as zero, taxing the same dollars a second time at distribution. This guide explains how the form works, why the pro-rata rule punishes most backdoor Roth conversions, and how to keep your basis documented for the next 30 years.