In May 1905, the Baghdad seniye lands commission submitted a 23-page report describing a conspiracy involving tribal shaykhs, merchants from the Tigris city of ‘Amara, and several local officials. According to the testimonies they collected, ‘Abd al-Qadir al-Khudayri, the wealthiest merchant in ‘Amara, had coordinated 6000 lira in bribes to local officials in order to secure the tax farm (iltizam) contract for the Majar al-Saghir mukataa for Sayhud, the paramount shaykh of the Al bu Muhammad. Sayhud, a powerful rebel and sometime-bandit, was not supposed to be given iltizam contracts. In fact, in accordance with the new Ottoman policy for Iraq, iltizams were supposed to be preferentially distributed to local cultivators on the basis of “chain guarantees,” whereby cultivators provided insurance for one another. Instead, the contract was given to Sayhud under a “false name” (nam-i mustear), and secured with a “strong” guarantee (kefalet-i kaviyye) – a mortgage on the property of his guarantor. It later turned out that as in many other cases, the mortgaged property had been wildly overvalued, and the guarantor was one of Sayhud’s underlings. While this case was unusually complicated, the basic pattern was not unusual. In particular, the use of false names and the overvaluation of mortgaged properties were common tactics for tax farmers – often tribal shaykhs – and their guarantors – often urban merchants – to accommodate an Ottoman legal landscape designed to prevent fraud, guarantee revenue, and deliver land to the cultivator. This paper will argue that new regulations around tax farms actually created more opportunities for new kinds of fraud. In addition, they incentivized the creation of financial networks involving shaykhs and merchants. ‘Abd al-Qadir Khudayri had previously acted as a guarantor for Sayhud in another large-scale operation that ended with both men in temporary exile – but before that, Khudayri used their partnership in Sayhud’s tax farms to completely monopolize the Tigris grain trade. That both men returned to ‘Amara and to their former behavior suggests that this kind of fraud remained both possible and profitable over several decades. Focusing on the relationship between Sayhud and Khudayri, this paper argues that Ottoman regulation of tax farm auctions in Basra province created new financial arrangements around land - and new possibilities for wealthy investors to cement their control of agricultural lands and trade.