Purpose: This paper aims to investigate the direct relationship between various types of business strategy; following Miles and Snow (2003, 1978) classification and measured by using Bentley et al. (2013) model, and operating cash flow downside risks – measured by using root lower in operating cash flow at a partial moment following Biddle et al. (2012) Model. In addition to investigate whether both types of accounting conservatism (conditional and unconditional) have a mediating role in explaining that direct relationship, or moderate it. Design/methodology: A time series of archival data is used, running Stata (V.17) as well as Path Analysis model - for investigating the mediating role of both types of accounting conservatism indirectly. Also, General Method of Moments (GMM) model - for investigating the moderating role of accounting conservatism’s both types, to solve the endogeneity problem associated with the possibility of a mutual influence between various types of business strategy and operating cash flow downside risks, robust standard errors used to eliminate autocorrelation between errors, and heteroskedasticity, using a sample of (104) non-financial companies traded on the Egyptian Stock Exchange, during the period from 2014 to 2023, while, the estimation period of the research model is starting from 2018, to facilitate the process of calculating research variables of interest. Results: In general, results indicate that no direct relationship between various types of business strategy and operating cash flow downside risks, due to the conditionality of this direct relationship on a third variable; accounting conservatism (that moderate the strength and sign of this relationship), especially after verifying the invalidity of accounting conservatism’s both types in mediating this direct relationship. Results also reveal a moderate, positive (negative) effect of conditional (unconditional) accounting conservatism on the direct relationship. Therefore, obviously, the impact of various types of business strategy on operating cash flow downside risks is not determined solely by type of business strategy alone, but within a broader framework of the practices of accounting conservatism’s both types. However, conditional accounting conservatism does not necessarily serve as an independent tool for reducing operating cash flow downside risks, especially, given higher levels of conditional conservatism compared to unconditional. This may lead -when adopting a high-risk prospector (versus defender) business strategy- to impression of excessive accounting pessimism, which contributes to increasing operating cash flow downside risks due to the exaggeration in the recognition of potential losses. In contrast, unconditional conservatism acts as a proactive tool, for recording losses based on cautious estimates not directly linked to specific adverse events. This enhances companies' ability to absorb shocks resulting from dynamic, high-risk nature of business strategies. Therefore, applying unconditional conservatism within reasonable limits balance risks associated with prospective business strategy and improves financial discipline during higher levels of uncertainty. Meanwhile, the absence of this type of conservatism when adopting defending business strategy may weaken the ability to respond to sudden risks, even if the environment is less complex. Accordingly, the researcher recommends aligning level of accounting conservatism with type of strategy adopted, for achieving balance between accounting caution and fair representation of the expected performance, in order to avoid practices that undermine the accuracy of forecasting operating cash flows. Originality/Value: For the researcher best knowledge, this paper is one of the first that applied in the Egyptian environment to address the ongoing debate on whether accounting conservatism’s both types (conditional and unconditional) have a mediating role in explaining that direct relationship, or moderate it. Thus, An empirical evidence from the Egyptian business environment for this relationship is provided. Furthermore, it highlights the various effects of the complementary relationship between various types of business strategy and both types of accounting conservatism on operating cash flow downside risks.