Built for Trucking Companies That Don’t Fit the Standard Insurance Boxes
When standard carriers say “no,” we help trucking businesses secure coverage quickly — including new ventures, recent authority changes, prior losses, or complex operations.
The Dragonfly difference
Experienced with hard to insure risks
Relationships across Excess & Surplus markets
Fast turnaround
Deep experitse in this market
Who We Help
Dragonfly Insurance works with trucking companies that traditional insurance markets struggle to support — not because they’re bad operators, but because their business is new, evolving, or doesn’t fit standard underwriting models.
You might be here because:
You’re a new venture or recently received operating authority
Your policy was non-renewed or canceled
Multiple carriers declined to quote
Prior losses or violations changed your risk profile
You added equipment, drivers, or routes and outgrew your policy
You were told coverage would need to be specialty or surplus lines
If that sounds familiar, you’re in the right place.
Trucking Operations We Commonly Work With
We regularly place coverage for:
New venture motor carriers
Owner-operators and small fleets
Power-only and leased-on operations
Hotshot and light-duty trucking
Local, regional, and interstate carriers
Specialized freight or non-standard cargo
If your operation isn’t listed, that’s okay — complexity is our focus.
The Dragonfly team is here to help you
Experienced With Complex Trucking Risks
Deep experience placing new venture and hard-to-place trucking risks
Established relationships across specialty and surplus lines markets
Familiarity with DOT filings, authority requirements, and compliance timelines
Fast turnaround when bind deadlines are tight
Clear guidance on pricing, structure, and coverage tradeoffs
Why Trucking Companies Choose Dragonfly
Most brokers focus on established fleets with clean loss histories — and avoid the rest.
We do the opposite.
What you can expect:
An honest, upfront assessment of what’s possible
Access to specialty trucking and surplus lines carriers
Clear explanation of tradeoffs (price, limits, deductibles)
Fast movement when you need coverage to operate
Support as your business stabilizes and grows
We’re not here to promise the cheapest rate.
We’re here to help you get covered — and stay on the road.
How It Works
1. Quick Intake
Tell us about your operation, authority status, equipment, and timing.
2. Market Assessment
We determine whether standard, specialty, or surplus lines markets are appropriate — and explain why.
3. Placement Strategy
We approach the right carriers, structure the submission properly, and move quickly.
4. Ongoing Support
As your operation matures, we help you improve insurability and expand options over time.
A Note on New Venture & Specialty Trucking Coverage
For new or complex trucking operations, coverage is often placed through specialty or surplus lines carriers. This can mean higher premiums, different policy structures, or stricter terms — especially early on.
What it also means is certainty, compliance, and the ability to operate legally.
We’ll be transparent with you at every step.