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Deadlines and Extensions · Seasonal Planning

Fourth-Quarter Deadline Crunch: Exchanges That Straddle the Year

In short

Sales closing after October 17, 2026 run into the April 15 return due date: how the extension rule, the installment method and holiday-season closings change a fourth-quarter exchange.

A relinquished property that closes on October 17, 2026 has a 180th day of April 15, 2027, which is also the due date of your 2026 return. Close one day later and the statute cuts your exchange period short unless an extension is on file. Add the holidays that fall inside a November or December seller’s 45-day window, and the fourth quarter is where exchanges most often fail on timing. This post sets out the dates, the extension rule and the installment-method fallback for an exchange that fails after December 31.

The “earlier of” rule and the October 17 line

Section 1031(a)(3)(B) says replacement property must be received by the earlier of 180 days after the transfer or “the due date (determined with regard to extension)” of your return for the year of transfer. Reg. section 1.1031(k)-1(b)(2) repeats the rule and counts in calendar days.

For a calendar-year individual, the 2026 return is due April 15, 2027. Counting 180 days:

  • Close October 17, 2026: day 45 is December 1, day 180 is April 15, 2027. No extension needed.
  • Close October 18, 2026: day 180 is April 16, 2027, one day past the due date. Without an extension your exchange period ends April 15.
  • Close November 16, 2026: day 45 is December 31, day 180 is May 15, 2027.
  • Close December 15, 2026: day 45 is January 29, 2027, day 180 is June 13, 2027.

Form 4868 gives an automatic six-month extension, to October 15 for calendar-year filers, and restores the full 180 days. The catch is that you cannot extend a return you have already filed: if you file in February because a refund is waiting, the due date stays April 15 and the exchange period ends there. The pages on keeping your 180 days with a tax extension and the tax-year straddle guide cover entity returns with earlier due dates and what to tell your preparer.

Holidays do not move day 45

The 45-day identification period is calendar days, and a deadline that lands on a Saturday, Sunday or holiday stays there. A November 16 closing puts day 45 on December 31, when title companies, lenders and intermediaries run short-staffed. A December 15 closing puts day 45 on January 29, after the market has been quiet for a month. The practical response is to have the identification letter drafted before closing and to deliver it early; see 45-day deadlines on weekends and holidays and how to identify replacement property.

If an identified property falls through after day 45, you cannot substitute; read what happens when an identified property fails after day 45.

If the exchange fails after New Year’s, the installment rules decide the year

An exchange that starts in 2026 and fails in 2027 does not always put the gain on the 2026 return. Reg. section 1.1031(k)-1(j)(2) coordinates deferred exchanges with the installment method of section 453. When proceeds are held by a qualified intermediary, or in a qualified escrow account or qualified trust, the determination of whether you have received a payment for section 453 purposes is made as if the intermediary is not your agent and without regard to the escrow security. Paragraph (j)(2)(iv) attaches one condition: you must have had a bona fide intent to complete a deferred exchange at the beginning of the exchange period, meaning it was reasonable to believe like-kind replacement property would be acquired before the period ended.

The effect is that an intermediary’s distribution of unused funds in 2027, after an identification period ends with nothing identified or after the exchange period expires, is a payment in 2027. Whether you may report the gain in 2027 under the installment method, and how depreciation recapture under section 1245 or 1250 is treated, depends on your facts; run it with your CPA using the planned page on Form 8824 when an exchange straddles two years and the Form 8824 instructions, which direct recognized gain to Schedule D, Form 4797 or Form 6252.

A fourth-quarter worked example

Hypothetical: you close the sale of a $1,000,000 rental on November 20, 2026 with $700,000 of equity. Day 45 is January 4, 2027; day 180 is May 19, 2027. Your return is due April 15, 2027, so you file Form 4868 in March to keep the May date. You identify three properties by January 4, including a Delaware statutory trust interest as the third. The first two fall through in March. The DST closes in April within the identified amount. If instead nothing closes and the intermediary returns the $700,000 in May 2027, the regulation treats that as a 2027 payment, and the gain question moves to the 2027 return, subject to the bona fide intent test. Run your own numbers with your CPA.

The reason sellers name a DST in the fourth quarter is closing speed. An investor buying a DST interest arranges no new loan, appraisal or inspection, so the closing does not depend on third parties the holidays slow down. See how quickly a DST can close when you are running out of time and the DST backup strategy. The guide to fourth-quarter and tight-deadline exchanges covers the direct-property side.

What to do now

  1. Write down day 45 and day 180 for your actual closing date, and check whether day 180 is after April 15, 2027.
  2. If it is, tell your preparer now that Form 4868 must be filed by April 15 and that the return cannot be filed early.
  3. Draft the identification letter before closing, with at least one replacement that can close quickly.
  4. If the exchange has already failed, do not have funds released until your CPA has read Reg. section 1.1031(k)-1(j)(2) against your dates; see what the intermediary may release after a failed exchange, then contact us about the remaining options.

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