我國自 1989 年以來即停徵證券交易所得稅,復兩稅合一施行後,公司取得之股利亦屬免稅,利用證券交易外觀,包裝應稅的股利所得,自然成為稅捐規劃/規避管道,稽徵機關為了維護稅權,面對疑似避稅的非常規安排,運用所得稅法第 66 條之 8 的規定,予以調查並發單補稅,進而視同非法逃稅的作法,衍生層出不窮的訟源。本文試圖藉由最高行政法院 2009 年判字第 1320號判決分析,來釐清合法節稅、脫法避稅及非法逃稅三者的概念與規範意義的區別。本文認為涉及 66 條之 8 之股權移轉避稅手法,其調整之正當性,係基於脫法規避股利所得之行為,不符證券交易免稅之稅捐優惠目的,勉強得以實質課稅予以調整,然進而比照短漏報、隱匿所得額之漏稅行為,予以裁罰,則有將脫法與違法行為混為一談之不當,更使得漏稅罰形同稅捐附帶給付,背離處罰法定原則與納稅義務人權利保護之基本精神。 Since 1989 Taiwan has suspended taxation on gains of securities transaction. The dividends received by a corporate is also tax exempt because of the combination of personal and corporate income tax starting from 1998. Using securities transaction as a form to cover the taxable dividends intended to pay to natural stockholders could be a way of tax evasion or planning. In order to safeguard the tax collectible the tax administrations use to apply of Article 66-8 of Income Tax Law against the suspicious and unreasonable transactions which may conceal the tax evasion intentions. This study aims to comment the decision of Supreme Administrative Court Year 2009 No 1320 and try to clarify the differences between these three concepts: tax saving, tax evasion and tax fraud. This study finds that, the tax adjustment in accordance of Article 66-8Income Tax Law and the principle of Substance –over-Form on the cases of securities transaction shall be justified only by the purpose of tax-exemption on securities gains. Such planning and transactioncan only be adjusted for tax purpose not even lead to tax penalty. Otherwise the tax penalty will be deem as violation of “ nullumcrimen sine lege, nulla poena sine lege” and taxpayer’s rights protection.