Dollar Stores Charging Sales Tax on Exempt Items

Some states like New York do not collect sales tax on medicine and most food items. Yet just about all the (now a dollar and up) small independently owned dollar stores I frequent will try to charge sales tax on medicine and tax-exempt food items. (Chains like Dollar Tree and major independents like Jack's on Herald Square follow the rules.)
 
After a few times of being asked for more money after carefully counting out 99 cents or a dollar, I started splitting out my order and telling the clerk "This batch of items is tax exempt." This usually allowed the law to be followed. But I just had some dollar store clerk clerk try to charge me sales tax on a pack of chocolate chip cookies and a bottle of short-dated ibuprofen. So, I asked him if he had New York State's list of taxable foods and beverages (Publication 880). He had no idea of what I was talking about.
 
What bothers me is that most people don't challenge this practice.

Out The 99¢ Only Stores scan everything and the computer knows what and what not to tax.  I watch as they're scanning an so far it's not wrong.

They got fined a few years ago for miss-scanning and overcharging so no the computer is used to stop the errors.

David_NYC


Some states like New York do not collect sales tax on medicine and most food items. Yet just about all the (now a dollar and up) small independently owned dollar stores I frequent will try to charge sales tax on medicine and tax-exempt food items. (Chains like Dollar Tree and major independents like Jack's on Herald Square follow the rules.)

New York has some of the most ridiculously complex sales tax regulations, anywhere. I recall a few years back the Daily News doing a report on paired up items, where one is tax exempt and another, similar or identical one, is not (for example, two products, one labeled "medicated" and the other not, both same ingredients list, but the one labeled "medicated" was exempt and the other one was not; marshmallows are taxable, but marshmallow kreme/fluff/etc. is not.

It is not surprising that the stores don't know about exemptions for all their items.

I've never noticed a problem here, but then ours is easy.  Only food, magazines/newspapers and prescription medicines are not taxable.  Everything else is.