On Nov. 2, 2023, dubbed the "day of the dead" by Stevie Stacionis, owner of Bay Grape wine bars in Oakland and Napa, the WineDirect point-of-sale systems collapsed, disrupting operations.

Stacionis had long complained about errors causing lost transactions and misreported sales. Point-of-sale (POS) systems, vital for Bay Area eateries, faced scrutiny after a major Square outage in September left businesses scrambling.

Despite recurrent glitches, some, like Stacionis, feel tethered to their chosen POS provider, facing challenges in switching. The reliance on complex technology brings benefits but leaves restaurants vulnerable when outages occur, impacting sales and customer satisfaction.

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