Workers' comp, licensing, and FLSA exposure are quietly stacking up inside off-duty programs across the country, and the cause is rarely the 1099 model itself. It's the vendor operating model built on top of it. This page unpacks what's actually in play, and how to preserve a program that already works.
Informational only. Not legal advice. Agencies should consult their own counsel.
Off-duty policing has grown into a category where legal and City Hall are no longer evaluating features. They are evaluating whether a vendor's operating model preserves the legal structure of a paid detail program, or changes it. Two 2025 cases have already put that question in motion.
The point of this page is not to talk anyone out of a 1099 program. It is to separate what preserves the legal foundation that makes a 1099 program work from what quietly erodes it, clearly enough that your city attorney, your finance director, and your union leadership can read it together.
Five items from the last twelve months that reframe how cities should think about their off-duty programs.
A 100-officer department averaging 10 off-duty hours per week at $50/hr accrues roughly $1.3M in unpaid overtime premium each year. Apply the FLSA three-year willful lookback plus liquidated damages and the number reaches about $7.8M, before attorney's fees, tax recalculation, or pension impact. Large metro agencies move from seven figures to nine.
Decided December 12, 2025. The court turned on control: the entity that manages the work carries the workers' comp liability, regardless of who claims to hold coverage. A vendor claiming "no control" is asserting a defense for itself, not a shield for the city that procured it.
Filed January 23, 2025. An FLSA class action against NYPD and the City itself. Settlements and class certifications are already underway, covering thousands of officers paid months late for off-duty security work. This is not a hypothetical exposure.
When off-duty officers are paid on a 1099, they absorb the full 15.3% self-employment tax, often without realizing it. That personal tax exposure sits alongside the department's classification risk under the FLSA economic-realities test, and it is the reason union leadership belongs in this conversation.
A vendor that recruits officers, guarantees pay from its own revenue, and accepts client funds directly is doing what a licensed private security agency does, regardless of the "platform" label. Where licensing applies, liability extends to whoever procured the unlicensed service.
An illustrative worked example on a mid-size department. The inputs are conservative. The math compounds fast.
Illustrative worked example for a 100-officer department. Large metro agencies move from seven figures to nine.
What The Account Is Told"Our vendor carries workers' comp on the officers, so the city is covered."
The Risk That Lands On The CityWorkers' comp coverage depends on an employment relationship, which depends on control. If the department controls the work (most do), the coverage may not survive a challenged claim, and the city likely carries the comp liability regardless of who pays the officers.
What The Account Is Told"Our vendor handles everything; it's just a technology platform."
The Risk That Lands On The CityA vendor that takes all client funds, guarantees officer pay from its own revenue, and coordinates assignments as its own operation may be functioning as an unlicensed private security agency. Licensing is triggered by function, not by calling yourself a platform. Liability extends to whoever procured it.
What The Account Is Told"Officers are 1099 contractors, so overtime and classification aren't our concern."
The Risk That Lands On The CityUnder the FLSA economic-realities test, officers paid even when the business isn't paid bear no risk of loss, which points to employee status. Reclassification turns every off-duty hour into overtime, with a three-year lookback and liquidated damages. Officers also carry silent personal 1099 tax exposure.
The control test, the Lassiter workers' comp fork, and the state licensing question are the three items counsel should pressure-test against the current vendor agreement.
The $7.8M worked example is the math on a mid-size program. Ask what a three-year FLSA lookback, plus liquidated damages, plus attorney's fees would do to next year's general fund.
The exposure runs to the city, not the department alone. Chiefs and command staff are usually the fastest path to getting counsel and finance engaged before a claim, not after.
If members are working off-duty as 1099s, they are carrying self-employment tax the department would otherwise share. That is a bargaining conversation, and it belongs on the table now.
Any single "we don't know" answer is a flag worth escalating. Two or more, and the exposure is in the architecture, not the 1099 classification itself.
Does the officer maintain a direct relationship with the business, invoicing and getting paid through that relationship, or does our vendor step into the middle of it?
Does our vendor take client payments directly and pay officers from its own revenue, or does money move through the agency of record?
If a workers' comp claim were challenged tomorrow on control, whose coverage responds, and does the answer hold up under the Lassiter framework?
Under our state's private security statute, does what our vendor actually does require a license, regardless of what the vendor calls itself?
Under the FLSA economic-realities test, would our off-duty officers be classified as employees, and what would a three-year willful lookback plus liquidated damages cost us?
Are our officers filing 1099s for off-duty work, and do they understand they are personally carrying the 15.3% self-employment tax?
A 1099 program works because the officer and the business maintain a direct relationship. When a vendor becomes financially responsible for officers, inserts itself between officers and businesses, or extends employment-related benefits, that legal structure begins to shift. RollKall was architected to avoid all three.
The officer maintains a 1:1 relationship with the business requesting their services and invoices that business through the platform. RollKall provides the infrastructure. It never becomes the employer, the staffing agency, or the middleman standing between them.
Money moves through the agency's structure, and officers invoice directly. RollKall never takes client payments and reissues officer pay from its own revenue, the pattern that starts to look like an employer rather than an administrative layer.
Every job, every hour, every payment, every policy check is logged and exportable. If counsel needs to confirm how the program is structured, the record already exists.
Insurance and other optional services are decisions officers make for themselves, not employment benefits RollKall extends on the department's behalf. That keeps the legal relationship exactly where the department intended it.
A 30-minute program risk review with someone who knows the case law, the FLSA math, and the licensing framework. We map your current vendor structure against the six diagnostic questions and hand the write-up to you. No obligation.
Informational only. Not legal advice. Agencies should consult their own counsel.
Cases referenced on this page: Lassiter v. Robeson County Sheriff's Dept. (N.C., Dec. 12, 2025); Piney v. City of New York (S.D.N.Y., filed Jan. 23, 2025). This material is informational, is not legal advice, and makes no representation about any specific vendor. Agencies should consult their own counsel.
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