In societies without national insurance of any kind, almshouses are the last refuge of penniless people.
In a functioning digital economy, being cashless is far different from being penniless, because cash is merely one form of money; but some preppers hoard gold in case the system gets destroyed and cashlessness suddenly becomes pennilessness.
(numismatics, of a country's system of money) Abstaining from the use of penny coins, despite having fully decimalized currency, via rounding of cash transactions (but not necessarily of cashless ones).
Canada became a penniless country in 2013 simply by rounding its cash transactions to the nearest nickel but otherwise not changing anything.