“Recent technological innovations hold the promise of streamlining legal research, managing massive due diligence projects, efficiently constructing contractual provisions, and analyzing inconceivably large quantities of data. But along with the excitement over the nearly limitless potential of rapidly advancing legal technology comes uncertainty about the future role of the human lawyer and a bevy of concerns for the profession. In artificial intelligence, attorneys see both a welcome liberation from picayune tasks and frightening implications for their work stream and the relevance of their existing skill set. While recent attention has been focused on new research and litigation capabilities, transactional and estate planning lawyers have utilized document automation and assembly software for decades. These programs can perform an array of functions, from populating repetitive fields in a simple purchase agreement to producing an entire portfolio of documents for a client’s estate plan. Like artificial intelligence programs, the proliferation of automation and assembly software presents both opportunities to improve the quality and efficiency of legal services and also difficult questions regarding the appropriate role of an attorney providing technology-assisted counsel. And despite decades of widespread use, scant attention has been paid to the ethical implications that reliance on technology may have on transactional practice. In particular, although automation can reduce technical errors and rapidly incorporate evolving laws and techniques, reliance on software creates risks of undue deference to computer-generated outputs and of temptation to undertake representations that strain an attorney’s sphere of proficiency. This Article addresses the expectations for effective transactional representation by highlighting several common missteps in typical transactional engagements. It then describes the increasingly sophisticated tools attorneys have used to more efficiently and effectively draft legal documents. The Article then turns to the potential of automation and artificial intelligence programs to eliminate drafting mistakes and to raise the standard of transactional practice. It implores caution, however, as attorneys rely more heavily on computer assistance in delivering legal services and products. As it becomes easier to generate a professional-looking work product in a wide range of complex areas of law, the risks of professional misadventure multiply. In this sense, technology amplifies some perils as it resolves others.