Best small business insurance for handymen and general contractors under $50/month

If you swing a hammer for a living, the "we need proof of insurance" email always seems to land right before the job you need. The good news for handymen, remodelers, and small general contractors: a basic general liability (GL) policy is one of the cheaper lines of business insurance you can buy, and plenty of low-risk trade profiles land under $50 a month for GL alone.

The catch is that "under $50/month" is a budget target, not a guaranteed price — your real premium depends on trade mix, payroll, location, and claims history. Below are the picks a budget-minded contractor should shop first, what each is good at, and how to keep the monthly number low without buying a policy too thin for your contracts.

Disclosure: CoverBench is reader-supported. When you get a quote or buy a policy through our links we may earn a commission via Commission Junction (CJ), at no extra cost to you. This never affects our rankings or recommendations. CoverBench is an independent comparison resource, not a licensed insurance agent or broker — this is general information, not insurance advice. Confirm coverage, terms, and current pricing directly with the insurer before you buy.

What "under $50/month" really buys

Based on published industry averages (not our own quotes), handyman general liability commonly lands in the mid-$50s per month. Industry cost guides such as Insureon and TechInsurance report a median around $55/month (~$660/year), with averages closer to $67/month once riskier trades are mixed in, and note that a large share of customers pay in the $35–$55/month range for GL. So "under $50/month" is realistic — it's the lower slice of a real published band, usually for a sole proprietor doing lower-hazard work (painting, assembly, light fixtures) rather than roofing or structural jobs.

These are illustrative ranges from public averages — not a quote, binding offer, or insurance advice. Your actual premium depends on your specific business, location, and the insurer, and rates change, so pull a real quote to confirm.

What pushes you over $50/month fast: high-hazard scopes (roofing, electrical, and plumbing can run GL 30–50% above a painting-only handyman, per published guides); employees on payroll (which usually triggers separate workers' comp); higher limits or contract-required endorsements; and a Business Owner's Policy (BOP) — which bundles GL with property/tools coverage and runs higher (published averages put a small-contractor BOP near $90/month), but can be better value if you own equipment.

How we ranked these (and why Hiscox leads)

We score insurers on four editorial sub-factors — online-quote speed, pricing transparency, coverage breadth for trades, and claims reputation — using published pricing, policy documents, and aggregated user reviews. We have not purchased or filed claims on these policies; this is research-based, not a hands-on test.

Hiscox ranks #1 for budget contractors for three non-commercial reasons: it quotes GL online in minutes, it offers monthly payment (what actually makes a policy feel "under $50/month" instead of a lump sum), and it's strong on low-risk trade and professional liability. Commission doesn't move that ranking — the marketplace and per-job picks below earn us the same or more, and we still rank them by fit.

The picks at a glance

*Illustrative only, based on public industry averages — not a quote, binding offer, or insurance advice. Confirm current terms with each insurer.

Check current options: Hiscox Small Business Insurance - Simply Business Marketplace - Thimble Insurance

1. Hiscox — best for cheap monthly GL on low-hazard trades

For a sole-proprietor handyman who mostly does lower-risk work and just needs a clean certificate of insurance to win jobs, Hiscox is the most direct route to a sub-$50 monthly GL policy. You answer a short online questionnaire, get a quote in minutes, and pay monthly rather than fronting an annual premium — usually the difference between a policy that "fits the budget" and one that doesn't.

Strengths: monthly billing is built in, so a ~$540–660/year GL premium (illustrative, from published averages) becomes a manageable ~$45–55/month; fast online quoting suits owner-operators who don't want a phone call; and its professional-liability strength helps if you also give advice, design, or consulting alongside the physical work.

Where it's weaker: the instant online path is geared to lower-hazard trades, so roofing, structural, or heavy-electrical work may route you to a custom quote — published reviews note its online appetite is narrower than a full marketplace. And like any single insurer, you only see Hiscox's price.

Best fit: a one-person handyman doing low-hazard work who wants the cheapest credible monthly GL with the least friction. Confirm the rate and covered scopes before buying — get a free quote from Hiscox.

2. Simply Business — best for shopping several carriers (and once you hire)

If you'd rather not bet your budget on one insurer's appetite, Simply Business is a marketplace: fill out one application and it returns quotes from multiple carriers so you can compare GL prices side by side. For a contractor chasing the lowest monthly number, that's the point — the "cheapest" GL policy is carrier-specific, and a marketplace surfaces more of them in one pass.

Strengths: multi-carrier quotes mean you compare real prices, not one insurer's rate — often the fastest way to find a sub-$50 option for your exact trade. Its other strength is workers' comp: the moment you put a helper on payroll, comp is usually legally required (confirm your state's rules), and Simply Business can quote comp carriers alongside your GL — handy if you expect to grow from solo to a small crew.

Where it's weaker: you're handed off to the chosen carrier for the policy and claims, so service quality depends on which insurer you pick, and weighing several options takes a bit longer than one instant quote.

Best fit: any contractor who wants to compare prices rather than trust a single quote — especially anyone who has, or is about to have, employees. Compare quotes through Simply Business and confirm current terms with the carrier you choose.

3. Thimble — best for seasonal and per-job handymen

Not every handyman works 12 months a year. If you pick up jobs seasonally or only need coverage for a specific contract, an annual policy can be poor value. Thimble is built for that pattern, offering on-demand coverage you can buy by the job, day, or month and generate a certificate of insurance on the spot.

A note on this pick: Thimble is here for honest comparison context. It is not currently a CoverBench affiliate partner, so we earn nothing if you choose it — we list it because it genuinely fits the seasonal/per-job case better than an annual policy would.

Strengths: pay-per-job or short-term coverage means a part-time handyman isn't paying for months they aren't working, and instant certificates are handy when a client demands proof for a single project.

Where it's weaker: for anyone working steadily year-round, an annual GL policy is usually cheaper per month than stacking per-job purchases, and on-demand products can carry tighter limits and fewer endorsements — check the coverage actually satisfies your client's contract.

Best fit: seasonal, part-time, or occasional handymen. If you work full-time, price an annual policy first — start with Hiscox or compare carriers on Simply Business.

How to keep your premium under $50/month

A few practical levers, drawn from published cost guides rather than our own testing:

1. Buy GL alone first. Standalone GL is the cheapest entry point; add property, tools, or a BOP only if you own equipment worth insuring.
2. Be precise about your trade, and right-size limits. Listing high-hazard scopes you rarely do can raise your rate 30–50%, while a $1M/$2M limit satisfies most contracts — don't over-buy, but never drop below what a client requires.
3. Re-shop yearly. Prices drift and your services change; comparing again keeps you at the low end of the band.

CoverBench's Coverage Fit Estimator shows which lines your trade needs (GL vs BOP vs workers' comp) and an illustrative monthly band before you request real quotes — an illustrative estimate from public averages, not a quote, binding offer, or insurance advice.

The bottom line

For most solo, low-hazard handymen, Hiscox is the quickest path to a credible GL policy that can land under $50/month, thanks to fast online quoting and monthly billing. If you want to confirm you're getting the lowest price — or you've started hiring — Simply Business compares several carriers (including workers' comp) in one pass. And if you only work seasonally, Thimble's on-demand model can beat paying for a full year you won't use. The monthly figures here are illustrative averages, not quotes — pull a real quote and verify current pricing with the insurer before you buy.

Frequently Asked Questions

Can I really get contractor insurance for under $50 a month?

Often, yes — for general liability alone, if you're a sole proprietor doing lower-hazard work. Published averages put handyman GL around a $35–$67/month range, so the under-$50 tier is realistic for low-risk profiles. Higher-hazard trades, employees, or a BOP bundle push the cost up. These are illustrative averages, not a quote — get a real quote to confirm.

What's the difference between general liability and a BOP?

General liability covers third-party bodily injury and property-damage claims and is the cheapest standalone policy. A BOP bundles GL with commercial property coverage, so it costs more — published averages put a small-contractor BOP near $90/month — but it can be better value if you own equipment worth protecting.

Do I need workers' comp as a handyman?

A true sole proprietor with no employees often isn't required to carry workers' comp, though some clients may still ask for it. Once you put someone on payroll, comp is usually legally required — but rules vary by state, so confirm yours. This is general information, not insurance advice. A marketplace like Simply Business can quote comp carriers alongside your GL once you hire.

Is it cheaper to buy direct or through a marketplace?

It depends. Buying direct from Hiscox is fast and can be competitive for low-hazard solo trades. A marketplace like Simply Business shows several carriers' prices at once — often the surest way to find the lowest rate, especially for higher-hazard work or once you have employees. Compare the actual numbers before deciding, and remember rates change.

Does CoverBench earn money if I buy through these links?

For some of them, yes. We may earn a commission via Commission Junction if you get a quote or buy through our Hiscox or Simply Business links, at no extra cost to you. We earn nothing from Thimble — it's listed purely for fit. Commissions never change our rankings; we recommend Hiscox first for budget contractors because of its monthly billing and fast online quoting, not payout.