#capital-gains
Track and report capital gains from investments
Section 1041 lets spouses transfer property tax-free during and after divorce, but carryover basis, the six-year window, QDROs, ISO conversions, and post-TCJA alimony rules quietly reshape every settlement. A working guide to what must be fixed before the decree is signed.
Section 1235 lets individual inventors and qualifying early investors treat a patent sale as long-term capital gain — even without a one-year holding period — if they transfer all substantial rights. This guide explains who qualifies as a holder, why the rule survived the TCJA carve-out for self-created intangibles, and how to draft the transfer so the IRS sees a sale rather than a royalty license.
Brokers often report a wrong or zero cost basis on Form 1099-B, especially for RSUs and ESPP shares. This guide explains covered vs. noncovered securities, Box 1e and Box 5, and how Form 8949 adjustment code B corrects basis so you do not pay tax twice on the same income.
Form 1099-B Box 1e shows your broker's cost basis, but Box 5 determines whether the IRS sees it. A working guide to covered vs. noncovered securities, Form 8949 adjustment codes (B, W, Q, O, T), and the RSU/ESPP basis corrections that prevent double-taxation.
Form 1099-S reports the gross sale price of a home, not the net, which routinely triggers IRS CP2000 notices for sellers whose gain is fully excluded under Section 121. This guide explains the Rev. Proc. 2007-12 certification that lets qualifying principal-residence sales bypass the form, the $250,000/$500,000 thresholds, the nonqualified use trap added in 2008, and how to defensibly report when the 1099-S cannot be skipped.
The OBBBA raised the Section 1202 QSBS cap to $15 million, lifted the gross-asset ceiling to $75 million, and replaced the five-year cliff with a tiered 50/75/100 percent exclusion at three, four, and five years — but only for stock issued after July 4, 2025.
A working guide to how the IRS computes boot in a Section 1031 exchange — cash boot, mortgage boot, the four netting rules, depreciation recapture at 25%, carryover basis, and Form 8824 reporting — with a worked example showing how $200K of fresh equity can wipe out $200K of mortgage boot.
Section 707(a)(2)(B) recharacterizes paired property contributions and cash distributions to LLC members as taxable sales when they occur within two years. A walkthrough of the two-prong test, the rebuttable two-year presumption, the four regulatory exceptions, debt-financed distribution mechanics, and the Form 8275 disclosure that keeps partners out of audit trouble.
A Section 83(b) election lets founders and early employees pay ordinary income tax today on the full value of restricted stock instead of at each vest. Filed within 30 days on IRS Form 15620, it can convert millions of phantom ordinary income into long-term capital gain and start the QSBS holding clock on day one.
Form 1099-DA introduces IRS broker reporting for digital asset sales beginning with 2025 transactions and adds cost-basis reporting for covered assets in 2026. Rev. Proc. 2024-28 simultaneously ends universal wallet accounting in favor of per-account allocation. This guide explains how investors and businesses reconcile 1099-DA against their own records, use the one-time safe harbor, and avoid paying capital gains tax twice.
Lifetime gifts under IRC Section 1015 carry over the donor's basis, while inheritance under Section 1014 steps it up to fair market value at death — a difference that can shift a family's after-tax outcome by six figures on a single appreciated position under the 2026 $15 million federal exemption.
Section 1248 recharacterizes part of a U.S. shareholder's gain on the sale of CFC stock as a dividend, capped by the corporation's earnings and profits and reduced by PTEP from GILTI and Subpart F inclusions. This guide explains who is affected, how the lookback works, why corporate sellers can prefer the recharacterization for Section 245A, and how to build a defensible work paper.
