Offer your thoughts or opinion on the input financial query or topic using your financial background.

Why do card processing companies discourage “cash advance” activities
Square charges a 2.75% fee (which the merchant pays), so you would be losing money if you only got a 1.5% cashback bonus. I would guess that the real reason Square prohibits you from getting cash is because of Visa/MC, state and federal regulations.  Visa/MC probably prohibit it for regular merchants due primarily to laws that are designed to prevent money-laundering. Certain merchants (like casinos) are allowed to give you cash advances against a credit card, but regular merchants are not allowed to do this. It is much more difficult to get Visa/MC to approve merchants to handle cash advances and they are subject to many additional regulations.  Services like Western Union will let you send cash with a regular credit card, but they are classified as "money transmitters" and must comply with additional state and federal regulations. If Square were to allow cash advances, this would likely subject them to a bunch of additional regulations.  It would cost them more to comply with these regulations and is outside their business model, so they simply prohibit it.