The article discusses the complexities surrounding the tax advantages of qualified small business stock (QSBS) as provided by Sec. 1202, particularly in estate planning. Besides offering a significant tax break for noncorporate taxpayers, it also presents several ambiguities especially concerning holding periods, QSBS stacking, the role of incomplete gift nongrantor trusts (INGs) and charitable remainder trusts (CRTs), the tax status of spouses, and transfers of QSBS. As IRS and legal clarity remains elusive on many related issues, the article recommends a coordinated approach among tax advisors, obtaining legal opinions, and possibly requesting private letter rulings from the IRS to mitigate potential risks.