There are around 4.9 million street vendors in India, a large part of the country’s informal sector workforce. Linked to India’s focus on digital economy and promotion of digital transactions, there is growing popularity of mobile payment (m-payment) applications or m-wallets such as PhonePe, Google Pay, Paytm, Bhim, and so on. This is also the case with street vendors, and the sight of a street vendor with a QR barcode for accepting payments is not uncommon. How do street vendors make sense of smartphone-based transactions in their lives? In qualitative interviews with street vendors in Srinagar city in Kashmir region in India, a complex picture emerged. Street vendors were mostly illiterate or had limited education, but were quickly adopting m-payments. For online transactions, QR barcode stickers were mostly displayed on carts of street vendors in Kashmir. However, at the same time, vendors had little or no understanding of these m-payment apps. They had limited language skills and had to take help of literate friends or family members to check transactions or to get over difficulties in operation. The use of these m-payment apps or m-wallet smartphone applications introduced new opportunities associated with digital payments. However, gaps in digital skills are pronounced, and remained a major challenge for the street vendors. During the course of fieldwork in Srinagar (2022–2023), we also observed that m-payment companies introduced technological solutions such as speaker-based instant audio confirmations for payments such as Paytm Soundbox and PhonePe Smartspeaker. This is indicative of the continuous tracking of the informal sector usage by such companies, and clearly they are aware and receptive of such gaps. However, market-linked technological solutions only address operational gaps, and do not address the underlying causes, including illiteracy, and knowledge or skill gaps. Such observations can be helpful in planning and implementation of government policies for street vendors in India.