Has anyone used TruBenefit or a similar Section 125 / PCMP / SIMRP benefits program with Square Payr

Hi everyone,

I own a restaurant and am evaluating a benefits program called TruBenefit Preventative Care Management Program. It appears to involve a Section 125 cafeteria plan, a Section 105(b) self-insured medical reimbursement plan, and a preventative care / wellness program that is supposed to create payroll tax savings while giving employees access to supplemental benefits.

The vendor materials say employees should see little or no reduction in take-home pay, while the employer may save on FICA taxes. Before I move any further, I’m trying to understand whether other Square Payroll users have implemented this type of program and what the real-world experience has been.

A few questions for anyone who has used TruBenefit or a similar PCMP/SIMRP/wellness reimbursement program:

  1. Was Square Payroll able to support the deductions and reimbursements properly?
  2. Were the deductions treated as pre-tax Section 125 deductions?
  3. Were any reimbursements or benefit allowances treated as taxable or non-taxable?
  4. Did Square require legal opinions, plan documents, or CPA instructions before setup?
  5. Did you run into issues with hourly, tipped, part-time, or variable-hour employees?
  6. What happens if an employee does not have enough gross wages in a pay period to cover the deduction?
  7. Could an employee end up with an arrears balance, direct bill, coverage lapse, or catch-up deduction after unpaid time off, vacation, illness, or missed shifts?
  8. Did this create any issues with minimum wage, overtime, tip-credit compliance, wage statements, W-2s, or Social Security/Medicare wages?
  9. Has anyone had the program reviewed by a CPA, ERISA attorney, or payroll compliance specialist?
  10. Any red flags, lessons learned, or things you wish you had asked before implementing?

I’m not looking for legal or tax advice from the community. I’m mainly trying to determine whether Square Payroll can practically support this type of arrangement and whether other restaurant or hospitality employers have had good or bad experiences with it.

Thanks in advance for any insight.

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