The Trailhead Blog

Payments, plainly. Plain-English guidance from Trailhead.

Short, honest reads on how payments, POS systems, and small business technology actually work — plus a weekly briefing on the merchant-services developments worth knowing about. Every news post cites its sources, and no article will ever promise you savings.

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A payment terminal beside a small-business POS operations briefing.
Featured·POS & Payments·4 min read

Square's August POS Update: What Small Businesses Should Actually Notice

Square's August 13 release added new pricing, tax, booking, inventory, and restaurant workflow controls. The bigger lesson: when comparing payment processors, operational fit can matter more than a small rate difference.

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Start with the fundamentals

News makes more sense on top of the basics. These guides cover how processing fees, statements, and POS decisions actually work.

How we write this blog

  • Sourced. News posts cite primary sources — card networks, PCI SSC, regulators, or the provider's own announcement.
  • Reviewed by a human. A Trailhead advisor reads every article before it publishes.
  • No savings promises. We explain what changed and what it means. We do not quote what you will pay or save.
  • Dated and corrected. Articles carry a published date, and substantive edits show an updated date.

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