Since the establishment of the “under-sheltering” puzzle (Weisbach, 2002) the literature in corporate taxation has sought to identify why some firms engage in greater levels of tax avoidance than others. To do so, studies have concentrated on debt contracting costs associated with tax avoidance (e.g., Shevlin, Urcan and Vasvari, 2013; Hasan et al., 2014). This topic is of particular importance given that the anticipated benefits (real and financial) from tax avoidance largely accrue to shareholders, while creditors, given their fixed claims on upside firm performance, assume most of the direct risks associated with tax avoidance (Hasan et al., 2014). In fact, recent evidence links tax avoidance with managerial rent extraction (Desai and Dharmapala, 2006, Desai, Dyck and Zingales, 2007), aggressive and non-transparent financial reporting (Frank, Lynch and Rego, 2009; Balakrishnan, Blouin and Guay, 2011), which are likely to further increase indirect agency costs associated with corporate tax avoidance. Importantly, however, despite documenting significant contracting costs (CCs from here on) associated with tax avoidance, the literature (Shevlin et al., 2013; Hasan et al., 2014) fails to explain the evidence that considerable number firms are able to pay significantly lower taxes for prolonged periods (Dyreng et al., 2008, 2016; GAO, 2008, 2016). One arguably valid reason for this observational divergence is that these studies do not take into account recent innovations in loan formation and contractual design alternatives or, more importantly how these contractual innovations help mitigate risks associated with tax avoidance. This is an important oversight given that advances in loan formation and covenant design help lenders expertly manage noticeably complex risk functions (BIS, 2003; Rajan, 2005; IMF, 2006), that are relatively eminent and substantial in comparison to taxspecific risks. For example, among the corporate-level risk disclosures, tax-position risks make up only 2% of the total risk function keywords in U.S. Securities and Exchange Commission mandated “risk factor sections” Campbell et al. (2012). 1 This observation is intuitive given that “direct” risks associated with tax avoidance will emerge only to the extent of tax-positional aggressiveness and/or the avoidance strategy can be successfully challenged by the tax authorities. I argue that if efficient loan formation and contractual design alternatives help facilitate credit risk diversification and/or borrower-lender incentive alignment (e.g., Simon, 1993; Armstrong, 2003; Bank for International Settlements, or BIS, 2003; Asquith et al., 2005; Manso et al., 2010; Mora, 2015), which enable lenders to take on relatively significant non-tax-based risks ( BIS, 2003; Rajan, 2005; IMF, 2006), then it is natural to expect these loan-level risk mitigation strategies to be ( at least) as effective for aggressive levels of corporate tax-positional risks. In that case, contracting costs associated with tax avoidance are likely to be lower than previously documented (Shevlin et al., 2013; Hasan et al., 2014) which provides an agencytheoric explanation as to how corporations can attain persistently low tax rates (e.g., Dyreng et al., 2008) without incurring material agency-specific costs. Accordingly, I re-examine contracting costs associated with corporate tax avoidance by focusing on a priori un-explored loan/borrower-level risk-mitigating mechanisms, and their role in alleviating agency costs associated with tax avoidance.