The increasing demand for Enterprise Resource Planning (ERP) solutions as well as the high rates of troubled ERP implementations and outright cancellations calls for developing effort estimation practices to systematically deal with uncertainties in ERP projects. This paper describes an approach-and a case study-to balancing uncertainties of context in the very early project stages, when an ERP adopter initiates a request-for-proposal process and when alternative bids are to be compared for the purpose of choosing an implementation partner. The proposed empirical approach leverages the complementary application of three techniques, an algorithmic estimation model, Monte Carlo simulation, and portfolio management. Our case study findings show how the ability of our approach to model uncertainty allows practitioners to address the challenging question of how to adjust project context factors so that chances of project success are increased. We also include a discussion on the implications of our approach for practice as well as on the possible validity threats and what the practitioner could do to counterpart them.M. DANEVA a business. They are the vehicles modern organizations use to achieve true business connectivity, a state in which everyone knows what everyone else is doing in the business all over the world at the same time. Analyst firms, such as AMR Research [1], Forester [2], Gartner [3], indicate that the demand for inter-organizational ERP solutions and the investments in ERP assets are continuously growing which, in turn, suggests that ERP represents one of the significant software (and software consulting) markets. We observe that ERP implementation has spawned an independent industry with firms providing consulting services exclusively and generating total revenue of billions of dollars. However, because of their relatively short history of existence, the business practices of requesting proposals for ERP implementation services, of bid preparation, and of pricing are not well understood. ERP adopters find themselves, increasingly more often than ever, caught in a situation in which they need to get initial estimates quickly, mostly based on uncertain assumptions, to compare bidding information from competing implementation service providers, and to initiate negotiations with them. For ERP adopters to be adequately prepared for this endeavor, they need to acquire knowledge (i) on how each consulting firm arrived at the bidding price and (ii) on how realistic the effort estimation figures, which one sees on the bidding document, are. However, at that early stage of requirements engineering (RE), more often than not, uncertainties of context interfere greatly with adopter's ability to assess to what extent the price they receive from the bidding document matches their organizational realities. Today, it is well known that a typical ERP project includes diverse configurations, each of which matches the needs of a unique stakeholder group, which, in turn, implies the presence of cost drivers unique to eac...