Square Payroll

gerichap54 — Sun, 21 Sep 2025 06:29:41 GMT

Can I use Square payroll to add an employee's company car usage to their w-2 at year end.

Also we are an S-Corp and reimburse S-Corp shareholders for health insurance - we also need to add that to W-2. Our current payroll service does this for us, so if I switch to Square I still need to be able to do these benefits.

Re: Square Payroll

DinaLRosenberg — Wed, 29 Nov 2023 13:34:40 GMT

Unfortunately you're going to have to call Square and ask. It sounds like you have some intricate payroll needs and I am not sure if Square would be the best bet for you to be honest. I currently use Square for payroll and it's difficult to get answers sometimes as the help I believe is out of the country and they don't know the ins and outs of payroll.

Last week I had an issue where I noticed a discrepancy between our quarterly federal 941 and our state filing. We are in the process of creating a health insurance plan and we required those documents for the health insurance company. There was a discrepancy in terms of number of employees and when I called Square support it was QUITE an issue explaining why this was a problem to customer support. The people that answer the phone aren't payroll professionals. They had to message a higher up and then I had to wait on the phone while they received the answer- then relaying it to me... no direct conversation with the person that actually understood payroll.

The discrepancy occurred because last year we made a 401k contribution and we needed it to hit the w2... the person at square support told my accountant to run it as a payroll instead of an off-cycle which screwed our entire federal quarterly up!

thankfully we were able to rectify the situation and did get approved for the health insurance...

But this is a cautionary tale. I used to run a 180k a week payroll for 80 employees back in the day- the questions I was asking square support were pretty basic payroll questions.. if you have more than basic payroll needs - and have special requests- it sounds like you need a specialized payroll company like ADP or Paychex.

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Square Payroll

Re: Square Payroll