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Canada Customs and Revenue Agency
Structured Settlements have become more attractive since the change of Interpretation Bulletin IT-365R2 May 8, 1987. The Interpretation Bulletin and Structured Settlements have been through many changes from 1977 until present. Section 5 reads as follows:

Structured Settlement

A “Structured Settlement” is a means of paying or settling a claim for damages, usually against a casualty insurer, in such a way that amounts paid to the claimant as a result of the settlement are free from tax in the claimant’s hands. To create such a structured settlement the following conditions must be complied with:

(a) a claim for damages must have been made in respect of personal injury or death,

(b) the claimant and the casualty insurer must have reached an agreement under which the latter is committed to make at least periodic payments to the claimant for either a fixed term or the life of the claimant,

(c) the casualty insurer must
i)   
purchase a single premium annuity contract which must be non-assignable, non-commutable, non-transferable and designed to produce payments equal to the amounts, and at the times, specified in the agreement referred to in (b).
   
ii)   
make an irrevocable direction to the issuer of the annuity contract to make all payments thereunder directly to the claimant, and
   

iii)  

remain liable to make the payments as required by the settlement agreement (ie, the annuity contract payout).

As a consequence of compliance with the foregoing conditions, the casualty insurer is the owner of, and annuitant (beneficiary) under, the annuity contract and must report as income the interest element inherent in the annuity contract while the payments received by the claimant represent, in the Department’s view, non-taxable payments for damages.

In Summary:

Settlement must be derived from a claim for personal injury or death


An agreement must be made between the Casualty Insurer and the Plaintiff to settle by way of a Structured Settlement


The casualty insurer must purchase a single premium annuity to produce the stream of periodic payments outlined in the settlement


The casualty insurer must be named owner, annuitant (beneficiary) of the annuity contract


The annuity contract must be non-assignable, non-commutable and non-transferable


There must be an irrevocable direction for payments to be made to the claimant

The casualty insurer must remain liable to make the periodic payments as outlined in the settlement agreement should the life insurer default