Vehicle-to-bicycle (VTB) technologies have the potential to increase cyclist safety but have not been well examined in different situations (e.g., weather, traffic flow). To address this research gap, we will conduct an accident-based simulation analysis to study the features of different VTB technologies and quantify the safety improvements for cyclists. We will also analyze to what extent these VTB technologies will be adopted by current vehicle fleets. We will use crash data from the Chicago online crash database from 2009 to 2014 maintained by Illinois Department of Transportation. This crash database provides detailed accident information including casualties, vehicle mode, accident reason, accident location, and road condition. With this information, we will build a statistical model for bicyclist injury prediction. Based on this model, we will summarize the typical road features causing traffic crashes between vehicles and bicycles, which will be fed into the simulation. The accident-based simulation will be conducted using the Simulation of Urban Mobility (SUMO), an open-source, highly portable, microscopic, and continuous traffic simulation package. We will record crash rates before and after different VTB technologies are implemented. Different VTB technologies will cause drivers and cyclists to react differently. Thus, we can quantify the safety improvement of these technologies under different scenarios, e.g., dry and rainy days. The variety of adoption possibilities will be assessed by developing a technology adoption predictor based on indicators from driver demographics, e.g., purchasing power. Finally, a quantitative safety impact assessment for cyclists will be conducted to measure the influence of various VTB technologies, including Blind Spot Detection (BSD), Bicycle to Vehicle communication (B2V), Intersection Safety (INS). This study will help local municipalities, drivers and cyclists identify what critical VTBs may improve cycling safety considering the variety of adoption possibilities and the advantages of those technologies.