Street vendors are an integral component of India's vibrant urban economy, providing critical goods and services to millions every day. In the past, street vendors have existed solely on cash transactions, taking advantage of the ease, intimacy and instantaneity that cash allows. But with the accelerated development of India's digital ecosystem and the government's aggressive thrust towards a cashless economy, the payment ecosystem is being rewritten. Even in the unorganized sector, there is a seen shift towards cashless payment systems like UPI (Unified Payments Interface), mobile wallets, QR code payments and card-based payments. Bengaluru, which boasts a thriving street vending culture and robust tech ecosystem, is the perfect setting to examine this change. This research delves into the way street vendors in Bengaluru have adjusted to the increase in digital transactions. Most vendors have already started adding digital payment options to their business operations, driven by customer preference, convenience, and security. Vendors said that accepting payments without cash minimized the risks involved in dealing with large amounts of cash, like theft or loss. It has also made it easier for them to manage their finances, as it is simpler to monitor sales, keep records, and plan business expansion more methodically. Others even stated that electronic records have enhanced their access to small loans and banking facilities, aligning them more directly with the formal economy. Simultaneously, the transition has not been flawless. Many vendors experience issues such as intermittent internet connectivity, particularly in dense markets or fringe urban areas, resulting in transaction failure or delays. Additionally, insufficient digital literacy and lack of experience in mobile payment platforms continue to be a hindrance for most, especially among older vendors less familiar with smartphones. Vendors also cited instances of technical errors while effecting transactions, along with concerns regarding fraudulent activity, cybersecurity threats, and instances of mistrust from customers regarding online payments. Managing both cash and digital payments simultaneously has added operational complexity, as vendors must cater to all customer preferences to avoid losing business. Despite these obstacles, the willingness to adopt digital payments is strong, particularly among younger vendors and those who see clear business advantages. Traders know that providing a variety of payment options makes them more competitive and assists in satisfying the changing demands of technology-savvy customers who want speedy, contactless transactions. The objective of this research is to investigate the adoption of digital payment modes by street vendors in Bengaluru, considering the advantages, disadvantages, and effects on their business operations. Primary data was gathered using standardized questionnaires and interviews from vendors from various sections of the city. For understanding relationships among variables like awareness, perceived benefits, perceived difficulties, and adoption intentions, Structural Equation Modeling (SEM) was utilized. It yielded an extensive picture of how the adoption of digital transactions is changing in the context of street vendors in an urban Indian setting. The research indicates that the transition to digital payments among Bengaluru street vendors is already in full swing but is not yet mature. There are many vendors at various stages of adoption, with some being early adopters and others being cautiously optimistic. While the advantages of improved financial security, opportunities for business growth, and customer trust are well-known, the hurdles such as technical problems, non-support and infrastructural obstacles need to be addressed systematically. This research underscores that if India's vision for a digitally inclusive economy is to be a success, it is essential to focus on empowering and facilitating even the smallest of the unorganized sector players. Strengthening infrastructure, providing easy-to-use training programs, providing affordable access to the internet, and establishing trust in digital systems are all important steps. Street vendors will be able to make a smooth transition into the digital economy, earning improved livelihoods, and supporting the urban economic ecosystem more securely if these support mechanisms are provided.