The permitted directions, as the statute lists them. Section 1035(a) allows the exchange of a contract of life insurance for another life insurance contract, or for an endowment or annuity contract, or for a qualified long-term care insurance contract; a contract of endowment insurance for another endowment contract whose regular payments begin no later than they would have under the old one, or for an annuity contract, or for a qualified long-term care contract; an annuity contract for another annuity contract or for a qualified long-term care contract; and a qualified long-term care contract for another qualified long-term care contract. Set out that way the structure is visible, and it reads more usefully as two rules about arrivals and departures than as a list. Nothing but a life insurance contract can be exchanged into life insurance, so an annuity or an endowment cannot be turned into coverage on a life. And nothing can come out of a qualified long-term care contract except another qualified long-term care contract, so value moved there stays in that form. The regulation states the first restriction outright rather than leaving it to be inferred. Treasury Regulation section 1.1035-1 provides that section 1035 does not apply "to transactions involving the exchange of an endowment contract or annuity contract for a life insurance contract, nor an annuity contract for an endowment contract", and that "[i]n the case of such exchanges, any gain or loss shall be recognized." The regulation predates the 2006 amendment that added qualified long-term care contracts, so the statute is the place to read that limb.
Two identity conditions travel with the transaction. The regulation limits a tax-free annuity-for-annuity exchange to cases where the same person or persons are the obligee under the new contract as under the old one, and requires the policies exchanged to relate to the same insured. In practice this is where attempted exchanges fail: changing the owner, the annuitant or the insured in the same motion is not an exchange of one contract for a comparable one, it is a disposition.
Basis carries over, which is the fact that makes the whole thing coherent. Section 1035(d)(2) sends the basis question to section 1031(d), under which the basis of the new property "shall be the same as that of the property exchanged", adjusted for money received and gain recognized. So the new contract inherits the old contract's investment in the contract rather than being treated as bought for the amount transferred. Two consequences follow that people consistently get backwards. A gain does not vanish: it sits inside the new contract waiting for a future withdrawal, surrender or annuitization. And a loss position survives too, which is the underrated half. Where a contract is worth less than its investment, exchanging preserves the higher basis, while surrendering for cash generally realizes nothing deductible on a personal life policy.
Boot is where the tax bill actually comes from. Section 1035(d)(1) cross-references section 1031(b) and (c). Under 1031(b), where an otherwise qualifying exchange includes "other property or money", gain is recognized "but in an amount not in excess of the sum of such money and the fair market value of such other property"; under 1031(c), a loss is still not recognized. Cash taken out at the exchange is the obvious case. The less obvious and far more common one involves a policy loan. The IRS's own instructions for Forms 1099-R and 5498, in the paragraph describing section 1035 exchanges, state that "the distribution of other property or the cancellation of a contract loan at the time of the exchange may be taxable and reportable on a separate Form 1099-R." So an owner who exchanges a loaned policy and lets the old insurer clear the loan out of the value, rather than carrying the debt across to the new contract, has generally received that amount. On a life insurance or annuity contract the resulting income is ordinary.
A partial exchange of an annuity is possible and carries a waiting period. Revenue Procedure 2011-38, which modified and superseded Revenue Procedure 2008-24, treats a direct transfer of part of one annuity contract into another as a tax-free exchange provided no amount, other than an amount received as an annuity for a period of ten years or more or over one or more lives, is received under either contract during the 180 days beginning on the date of the transfer. A withdrawal inside that window puts the characterization of the whole transaction back on general tax principles and the facts. The procedure also states that the Service will not require the pre-existing contract and the new one to be aggregated, even where the same insurance company issued both.
What an exchange does not do. It does not waive a surrender charge still running on the old contract, and the replacement generally starts a fresh surrender schedule of its own, so a contract three years from the end of its charge period can come out of an exchange with another seven or ten years to run. Sales compensation is payable on the new contract, which is why the exchange decision and the product decision are worth separating: the honest question is whether the replacement contract is better on its own terms, and the tax deferral is a condition rather than a reason.