thread Re: How do I add health Insurance for S-Corp to W-2 Box 1? in Staff & Payroll

How do I add health Insurance for S-Corp to W-2 Box 1?

Volksburgs — Sun, 21 Sep 2025 06:30:57 GMT

I want to include health insurance premiums paid for a 2% shareholder in TAXABLE income (W-2, Box 1), but I'm not subject to any payroll taxes (FICA, Medicare, SDI), so they should NOT show up in Boxes 3 and 5. Anyone know how to do this?

Re: How do I add health Insurance for S-Corp to W-2 Box 1?

Bronze_Palms — Wed, 11 Oct 2023 23:52:30 GMT

Following.

Re: How do I add health Insurance for S-Corp to W-2 Box 1?

LaurenSQ — Tue, 07 Nov 2023 21:07:17 GMT

Hi @Volksburgs @Bronze_Palms Square Payroll collects S-Corp health insurance premiums at the end of the year and will be sending an email to all S-Corps using Square Payroll in early December. The premium amounts will be added to Box 1 (Wages), Box 14 (Other), and Box 16 (State Wages) but not included in Box 3 (Social Security Wages) or Box 5 (Medicare Wages and Tips) on Form W-2 as you noted!

Re: How do I add health Insurance for S-Corp to W-2 Box 1?

Brightsidebody — Sat, 09 Dec 2023 21:18:18 GMT

I have not received an email yet to add s-corp health insurance premiums to w2 wages. Has this email been dispersed yet?

Re: How do I add health Insurance for S-Corp to W-2 Box 1?

_Violet — Sun, 10 Dec 2023 18:47:02 GMT

Hi @Brightsidebody - Thanks for following up on this thread.

To help you answer your question, I recommend that you connect with the Square Payroll support team. If you haven't already, please reach out to Support directly by logging into your Square account and heading here.

Re: How do I add health Insurance for S-Corp to W-2 Box 1?

LaurenSQ — Mon, 11 Dec 2023 17:19:49 GMT

Hi @Brightsidebody emails to businesses listed as S-Corp on Square Payroll were sent last week. If you are an S-Corp and didn't receive it, it may have gone to your spam email. Luckily, this year, businesses no longer need to email the amounts to the Square Payroll support team.

Regardless if you received the email or not, starting this year, all S-Corp businesses can now report their S-Corp health insurance premiums through Dashboard by going to Payroll > Year End Checklist. Submissions will be reflected immediately upon re-downloading your draft W-2s and are reported in Box 1 (Wages) and Box 14 (Other). The deadline to submit the premium amounts for 2023 is January 4, 2024.

If your business is not listed as an S-Corp on Square Payroll and you need to report premiums, you can contact the Square Payroll support to have them temporarily update your business type to S-Corp which will allow you to submit the 2% health insurance premium amounts through Dashboard.