Square payroll rep support is pranking me...

Shamistalib — Fri, 02 Jan 2026 17:43:08 GMT

I legit have a heachache. I am a pretty down to earth and understanding human being but Square payroll support has made me want to pull my hair out.
I have never dealt with this type of incompetence in my entire life.

My issue is the figures on my independent contractor employee's 1099-NEC is wrong. I only have 2 contractors with 11 payments total between the both of them.
I contacted support by phone first. Complete waste of time. It's like he was purposely talking to me in circles. Asking me irrelevant questions, I mean completely irrelevant. Requesting a screenshot. Saying the screenshot is blurry. Then admitting that he has access to view the page of the same screenshot I was trying to send.
We went back & forth of me trying to explain to him my simple problem and him trying to comprehend so I disconnected.. for my sanity.

I enter the chat.
Me: The "non employee compensation" figures you have listed on the 1099's you created for my contract employees are INCORRECT (uploads 3 screenshots)

Chat: Thanks for reaching out to Square, My name is Alex. Can you please confirm with me if you are referring to your employees 1099-K form?

Confused Me: 😕 No my contractors 1099 Nec. I've upload screenshots of the form. Do you not see it?

Chat: I see them but I'm trying to figure out what's the issue.

Me: Reiterates

Chat: Can you please confirm with me why are you stating that they are wrong?

Me: Sure. In the other screenshot (the payroll history) you can see the amounts and when those are added together, the totals do not match.

Chat: Thanks for contacting Square support. We are currently experiencing high chat volume....

Like am I being pranked right now? Did the support agent just exit our chat? lol. So I wait. Confused. Shocked.
15 minutes go by same chat window up

Chat: Welcome to square. Name & email
Me: supplies info
Chat: Give me a sec to review
Me: sure
Chat: Thanks one moment
5 minutes go by...
Chat: The chat will end in 5 minutes click yes to continue
Me: Yes, continue
Chat: The chat will end in 5 minutes click yes to continue
Me: Yes continue......

And I'm still here waiting, hoping to get someone to help me correct the amounts on these 1099.

Has anyone else experienced this type of tomfoolery? If so, how do you handle it? HELP!

Re: Square payroll rep support is pranking me...

DinaLRosenberg — Fri, 02 Jan 2026 20:26:48 GMT

I also use square payroll and the one time I had to call support it didn't go well. Honestly it's required to provide robust, near instant help when it comes to payroll concerns as we're talking about people's lives here.

What you describe is so incredibly frustrating.. did any of your 11 payments happen close to the turn of 2024/2025? Sometimes the way the payroll run is dated can be an issue. My payroll for the last period in December, for example, counts toward January 2026

thread Square payroll rep support is pranking me... in Staff & Payroll

Square payroll rep support is pranking me...

Re: Square payroll rep support is pranking me...