In 1616, the English East India Company expanded its trade into Safavid Iran. The chief merchants in India hoped to acquire a significant share of the Iranian silk trade. After several difficult years in India, the English traders in Surat felt pressure to establish a solid foundation in Iran where they could redirect Iranian silk through Iran’s southern ports and onto Company ships for Europe. Despite Robert Sherley’s promise of wealth and a prosperous market for English cloth, many in the English camp, predominantly Sir Thomas Roe, objected to the silk trade on grounds that it was generally a risky venture. But several leading merchants dismissed Roe’s concerns and pursued the trade without his approval. After early indications that the venture had potential for success, the English silk trade quickly began to falter and finally ceased to exist by 1640. Although its demise was once described as the Company’s failure to produce a substantial quantity of purchasing power—eastern goods, precious metals, and English commodities—this paper explores an alternative explanation that suggests the Company’s failure in Iran was not exclusively the consequence of poor economics.