The Big Issue is launching trials to allow its magazine sellers to accept payments with contactless technology.
The organisation has teamed up with technology company iZettle to test the idea in London, Bath, Birmingham, Bristol and Nottingham.
The aim is to roll the initiative out nationally, in an effort to improve financial inclusion and better serve those who have difficulty accessing financial services and products offered by retail banks.
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The Big Issue said it wanted its vendors to continue to make a living in an increasingly cashless society amid a huge shift in consumer spending.
Russell Blackman, managing director of the Big Issue, said: "We have long-recognised that we are operating in an increasingly cashless society.
"Big issue vendors are microentrepreneurs, effectively running their own small businesses, so understandably there are many who are keen to respond to market forces and offer their customers an alternative to cash.
Image: Louise Haywood-Schiefer/PA Wire
"The partnership with iZettle reflects our shared values and commitment to creating a more financially inclusive society, supporting those whose lives have been blighted by poverty and a lack of opportunity.
"The Big Issue looks forward to providing our vendors with the opportunity to cater for their customers' needs and increase their ability to earn a legitimate income."
Mary Holden, 52, who sells the magazine in Victoria, central London, said: "My customers have been asking for the option to pay by contactless for some time.
"It's brilliant news that the Big Issue are moving with the times and we can now offer our customers the option to pay by contactless. I hope I see my sales go up as a result."
Edward Hallett, managing director at iZettle, said: "We're constantly looking at ways we can aid financial inclusion so it's fantastic that we've been able to partner with the Big Issue, giving sellers access to tools that will help them manage in an increasingly cashless society.
"Now, people who aren't carrying cash can simply tap-to-pay and show their support by buying a magazine. Our partnership ensures that vendors never have to miss out on a sale again."