I’m a 100% shareholder of an S-corporation with no employees. I know that my health insurance premiums and HSA contributions are added to salary. In my situation, I’m not paying myself in 2019 until 3/15/19 (I pay myself monthly each 15th). However, I will be making health insurance premiums payments and HSA contributions in January and February. How do I handle this situation from a payroll stance? Like, how do I add my January and February health insurance premiums and HSA contributions to salary when I won’t be taking a paycheck those 2 months?
When you run a 3 month payroll it should pick up everything over the three months unless you have something set to post only per payroll run instead.
And actually in your situation I would run payroll in Jan and Feb but deduct the net to shareholder loan and then in March draw the repayment of the loan. Keeps things running timely (You will have to pay taxes as earned in J/F)
It isn't clear who guided you to only pay yourself quarterly, because you told us you are taking company funds monthly for that benefit to you, personally, as the employee. The employee-shareholder requirement is for Payroll as Reasonable Rate for services performed, and using the company money but delaying reporting this as a Payroll event, as taxable, is pretty much violating that requirement. While there is a strategy for After the Fact payroll, it isn't used with something so obvious and, to use a phrase I use in class = Discoverable. You have a Monthly activity that relates to Payroll, so you should be running this through Monthly payroll, at a minimum frequency. Not Quarterly.