Is it illegal to pay for personal items with a business checking account?
It's not uncommon for smaller businesses, in particular, to blur the lines somewhat when it comes to dipping into the wrong pocket for personal expenses. That seems to be quite true, for example, when it comes to sole proprietorships. Frankly, there's nothing illegal about a sole proprietor dipping into business assets to take their family out to a nice meal, because the business is not a separate legal entity. It would become a problem, however, if the same sole proprietor tried to treat the cost of that meal as a business expense when reporting his/her business income on a tax return.
Where the line between business expenses and personal expenses gets a lot sharper is when the business is a partnership or corporation. In those cases, using the business's assets for personal purposes takes money away from the other owners of the company, and could be considered stealing.
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