Due to the ever-increasing complexity of income tax laws in the United States, the number of US taxpayers filing their taxes using tax preparation software (henceforth, tax software) continues to increase. According to the U.S. Internal Revenue Service (IRS), in FY22, nearly 50% of taxpayers filed their individual income taxes using tax software. Given the legal consequences of incorrectly filing taxes for the taxpayer, ensuring the correctness of tax software is of paramount importance. Metamorphic testing has emerged as a leading solution to test and debug legal-critical tax software due to the absence of correctness requirements and trustworthy datasets. The key idea behind metamorphic testing is to express the properties of a system in terms of the relationship between one input and its slightly metamorphosed twinned input. Extracting metamorphic properties from IRS tax publications is a tedious and time-consuming process. As a response, this paper formulates the task of generating metamorphic specifications as a translation task between properties extracted from tax documents - expressed in natural language - to a contrastive first-order logic form. We perform a systematic analysis on the potential and limitations of in-context learning with Large Language Models(LLMs) for this task, and outline a research agenda towards automating the generation of metamorphic specifications for tax preparation software.

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