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Estate planning is the arrangement and management of an estate owner’s estate to the effect that the estate owner and his beneficiaries can enjoy maximum benefit from his worldly possessions during his lifetime and after his death. Unfortunately, for estate owners and their beneficiaries, a deceased estate has to pay an executor’s fee, estate duty and capital gains tax on the demise of the estate owner, which means the amount the estate owner intended his heirs to receive, might be substantially decreased. For decades trusts have been used for estate planning purposes. The decision of the estate owner to utilise a trust for estate planning purposes involves the disposal of growth assets from the estate owner’s estate to the trust. This ensures that the value of a growth asset is pegged in the estate owner’s estate and the asset continues to grow in the trust. The asset is disposed of by way of a loan account in favour of the estate owner and the parties agree that the outstanding amount is payable on demand. In his will, the estate owner then bequeaths the outstanding amount back to the trust. However, Paragraph 12(5) of the Eighth Schedule to the Income Tax Act 58 of 1962 stated that capital gains tax will be levied in cases where a debt is reduced or discharged by a creditor for no consideration or for an amount which is less than the outstanding amount. In ABC Family Trust ITC 1793 the estate owner transfer assets to the trust on a loan account and in her will, bequeathed the exact outstanding amount back to the trust. It was argued on behalf of the trust that the bequest constituted a set-off and not a discharge of the debt. However, the court stated that the set-off took place because of the “operation of law” which is specifically included in the definition of a “disposal” for capital gains tax purposes. The court applied Paragraph 12(5) and found that the trust is liable to pay capital gains tax on the full outstanding amount. In XXX Trust ITC 1835 the estate owner also transferred asset to a trust, but in her will she bequeathed the residue of her estate, and not the exact outstanding amount, to the trust. In this case the court placed emphasise on the intention of the estate owner and not on the possible application of Paragraph 12(5). The court found that it was not the intention of the estate owner to discharge or reduce the debt for no consideration. Subsequently, it was found that the trust is not liable for capital gains tax. Since these two cases Paragraph 12(5) has been deleted and Paragraph 12A inserted in the Eight Schedule to the Income Tax Act 58 of 1962. The focus of this mini-dissertation is to determine which estate planning tools were available to estate owners to prevent a capital gains liability under Paragraph 12(5). The capital gains tax effect that Paragraph 12A might have on estate planning is also discussed. / LLM (Estate Law), North-West University, Potchefstroom Campus, 2014