At this time you are unable to pay independent contractors through Square Payroll. It is intended solely for employees, not independent contractors (also known as 1099 Contractors). I am more than happy to bring this back to our product team as a requested feature! 

Having the ability to enter independent contractors (1099 forms) with the W2 Tax information would be outstanding! Is there any plans in the near future to include this service. If not, can you recommend a service that will work with the square?

@PPS_IX_Security - While this is definitely a popular feature request from our sellers, I can't speak to potential feature releases. As for workarounds, I'm not familiar with any 3rd party options. Hopefully someone else in the community has some experience with this topic and shares their thoughts! 

I have this same question. I noticed in another thread how some are paying commission only, and the solution did have a workaround.  I'm curious if I could use the commission feature only, and enter the withholdings as "0", and just not supply a W2 at the end of the year, but instead use another system to issue a 1099 based on the payments made.  At least I'm only having to generate 12 1099's manually, rather than all the work that currently goes into processing payroll from three different systems.  Would that technically work?  

@GlamSquadKW - Since Square Payroll is intended solely for employees, not independent contractors (also known as 1099 Contractors), this would not work. However, I'll be sure to let you know if this feature becomes avilable in the future! 

Sean,

I am having an issue with setting up my payroll for independent contractors. At the moment, I am the owner and the only employee. With that said, I am having hell of a lot of trouble getting my "Unemployment Tax Employer Account Number". I am not liable for unemployment, therefore I do not need an EAN. With that said, I tried to get one, but I am not allowed. This is extremenly frustrating, as I am just trying to set up 23 independent contractors and this small feature is keeping me from continuing further.

Hi @Grabit, I'm so sorry for the frustration this caused. 

I have good news! As of today you can add independent contractors (who receive a 1099-MISC form only) to Square Payroll without an Unemployment Tax Number.

To get started:

1. Navigate to the Payroll section of your Square Dashboard.
2. Click Get Started > Select your state.
3. Click Contractors Only and then click Save & Continue.
4. Follow the prompts to provide information about your business and then add contractors to your payroll.

You'll be able to add independent contractors to Payroll, and you won't need to enter an Unemployment Tax Number at any time. (Please note, you will need to enter your EIN.)

This option is brand new so let us know if you have any questions or feedback! 

Can independent contractors onboard themselves as an LLC, rather than an individual?

Hi @davej, it's not possible for contractors to onboard as an LLC (with an EIN) at this time. They'll need to use their SSN instead. If this changes in future we'll update this thread to let you know.

Hey @IRresumes  - great question! 

Yes, you can still pay these contractors through Square Payroll, we just won't file a 1099-misc for them if they use their EIN. 

@JustinC so under payroll, instead of the SSN, do I just enter their EIN?

Thanks for clarifying.

@IRresumes - you got it! 💪🙌

@milee - I found a thread that should guide you in the right direction. Look at the links Sean included in his best answer at the top.