A failed exchange doesn’t mean financial disaster.
Model home with paperwork, calculator and pencil

A 1031 exchange, named after Section 1031 of the Internal Revenue Code, allows real estate investors to swap one investment property for another while deferring capital gains taxes. Of course, the magic of exchanges for your clients is the ability to use real estate investment the way some people use tax-deferred retirement accounts, such as 401(k)s and traditional IRAs. With the ability to roll proceeds from a property sale into new property investments, clients build wealth and avoid paying capital gains taxes on sales gains until their final sale.

However, sometimes a 1031 exchange transaction will fail, and that’s where a commercial real estate practitioner’s expertise comes in. An estimated 8%–10% of 1031 exchanges fail to complete. The most common reasons include:

  • Missing the IRS’s 45-day deadline for identifying a replacement property
  • Failing to close on the replacement property within the 180-day limit
  • Inability to find suitable like-kind replacement property
  • Replacement property value falls short of the relinquished property

When that happens, your client may face a sizable tax bill. But a failed exchange doesn’t have to mean financial disaster. There are strategic ways to minimize the damage, particularly through tax straddling and the installment method.

The Tax Straddling Strategy

When you sell property within 180 days of the end of the year, the like-kind exchange is not required to be completed before the end of the year. This means the exchange will carry over from one tax year to the next and is often referred to as a “tax straddle.”

A qualified intermediary holds the proceeds from the sale during the period before the replacement property is purchased. In the case of a tax straddle, the proceeds from the sale would not be released from the QI to the taxpayer until the subsequent year.

This timing difference can be a game changer for your tax liability.

1031 Specialists, a 2025 NAR REACH Commercial company, offers a dynamic platform for qualified intermediary services across all 50 states and 384 metropolitan statistical areas, with an attorney guarantee and “pay when you close” policy.

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The Installment Method

If the taxpayer fails to complete their Section 1031 exchange, the installment method can allow them to defer paying capital gain taxes from the sale of an investment property. Under the installment method, gains from a sale are recognized in the year cash is received by a taxpayer.

This one-year deferral can provide significant tax planning opportunities and breathing room to manage the impact.

The installment method is only available to taxpayers who make a bona fide attempt to complete the like-kind exchange. It is not available when there is no intention of purchasing replacement property. Without proper documentation, the IRS may disallow the installment method treatment.

Keep detailed records of the exchange attempt, including:

  • Communications with real estate professionals
  • Property identification documents
  • Inspection reports and due diligence materials
  • An explanation of why the exchange failed

When You Can Still Save It

Not every exchange failure is permanent. Depending on your situation, you might be able to salvage the transaction:

PARTIAL 1031 EXCHANGE: A partial like-kind exchange requires investors to pay capital gains taxes on the boot but allows them to defer the tax liabilities of the portion used to purchase the replacement property.

MULTIPLE REPLACEMENT PROPERTIES: Purchasing multiple replacement properties can help ensure there are no proceeds left over after the transaction is complete.

Tax Straddle Windows

There are two ideal windows of opportunity for selling a property with the intention of completing a 1031 exchange. One is the period from Nov. 17 through Dec. 31 (the last 45 days of the tax year). If the sale of your relinquished property closes during this window and you fail to properly identify replacement properties by Day 45, you won’t take receipt of funds until after the first of the year.

Tax straddling is also possible for sales that close between July 5 and Nov. 16. In these cases, if you are able to identify replacement properties, yet unable to complete your acquisition, Day 181 will fall after the first of the year.

Remember: a failed 1031 exchange isn’t the end of the world. With proper strategy and professional guidance, your clients can still minimize their tax liability and position themselves for future success.

Author Jon Hilley is managing partner of 1031 Specialists in Denver.