How Technology Is Fixing Broken Contractor Insurance Tracking
August 19, 2025

Shayne Gaffney

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Subcontractor insurance tracking sounds simple until a certificate expires and no one realizes it. Suddenly, what should have been routine paperwork turns into real financial risk. If something goes wrong, the liability lands on you.

The problem is that most teams still rely on outdated tools to handle contractor insurance verification. Spreadsheets, inboxes, and shared folders create blind spots that leave projects exposed. This article explains why manual tracking fails and how modern solutions close the gaps before they cost you.

What Is Subcontractor Insurance Tracking?

Subcontractor insurance tracking means collecting and verifying proof that a contractor has the right insurance coverage in place to work on a project. It’s how general contractors, project owners, and facility managers shift risk off their books and meet contractual obligations.

Verifying subcontractor insurance starts with checking that each contractor has the right types of coverage in place. This usually includes:

  • General liability
  • Workers' compensation
  • Automobile liability
  • Umbrella or excess liability
  • Any project-specific or specialty lines

Each contractor provides proof of coverage through a document called a certificate of insurance (COI). But collecting the certificate is just the first step. The real challenge isn’t getting the certificate. It’s making sure the coverage is correct, keeping track of when it expires, and staying ahead of renewals. That’s where most teams get stuck.

Why Traditional Insurance Tracking Falls Short

Manually tracking COIs might work on a small project, but as more contractors, projects, and timelines overlap, the process breaks down fast. Here’s what that usually looks like:

  • COIs are sent via email: Contractors send attachments when prompted, often in inconsistent formats or without naming files clearly.
  • Admins download and save them to folders: Some are labeled correctly. Some are buried three layers deep in a shared drive. Some never make it in at all.
  • Someone logs details into a spreadsheet: That person might not be trained to catch missing endorsements, outdated coverage, or policy mismatches.
  • Expiration dates are tracked in a calendar or task manager: Reminders are set manually, sometimes based on the “Received Date,” not the actual expiration.

When subcontractor insurance tracking relies on disconnected tools like spreadsheets and shared drives, small gaps multiply fast. Most of the time, those gaps stay hidden until a site audit is due, a crew can’t start work, or an incident forces someone to pull a certificate for verification.

Those gaps can also lead to real financial consequences. Around 35% of businesses receive unexpected premium audit bills, often due to underreported subcontractor costs or missing documentation during audits. Without clear proof that subcontractors carry their own insurance, businesses risk being charged as if those subcontractors are uninsured labor.

What’s at Stake for Safety and Operations Teams

An expired or inaccurate COI doesn’t just delay a project. It can:

  • Void your risk transfer: If the coverage listed doesn’t meet the contract, the risk stays with you.
  • Leave you exposed to uncovered incidents: Especially in cases of injury or property damage, costs that can climb fast.
  • Trigger a breach of contract: Which can impact payment terms, insurance obligations, and future bidding opportunities.
  • Invite lawsuits or stop work orders: When clients or regulators uncover a compliance failure, projects can get shut down or legal teams get involved.

There’s another issue safety teams face: misclassification. In construction, 24% of employers misclassify up to 48% of subcontracted workers, which means those workers often lack proper coverage.

Misclassification happens when subcontractors are treated like independent businesses but work more like employees. If one of those workers gets injured, the liability often shifts back to you as the hiring contractor.

That’s why COIs aren’t enough. Even if the paperwork looks right, your project might still be exposed. Safety and operations teams need more than documents on file. They need confidence that every contractor carries the right coverage, and that it matches the job’s actual requirements.

What Better Insurance Tracking Looks Like

A modern subcontractor insurance tracking system doesn’t just store documents. It verifies them, keeps them current, and makes requirements easy to match and manage. That means fewer surprises, faster onboarding, and better coordination between safety, legal, and procurement teams.

Key features to expect:

  • Centralized document storage: Everything lives in one place, version-controlled, searchable, and accessible across departments.
  • Automated COI collection and renewal requests: The system follows up automatically when expiration dates approach, reducing back-and-forth and helping subs stay on track.
  • Expiration tracking with real-time alerts: Teams get notified before there’s a gap, giving them time to act without holding up work.
  • Project- and client-specific requirement matching: You can define what’s required for each job and see instantly whether a COI meets those terms.
  • Dashboards that keep everyone in the loop: No more “Did we get that updated certificate?” Slack messages or email chains. The information is right there, updated in real time.

With the right system in place, compliance becomes proactive, not reactive. That’s the shift Highwire supports, replacing outdated tools with something designed for the way your team actually works.

How Highwire Fixes the Problem

Highwire doesn’t just organize insurance documents; it changes contractor insurance verification into a faster, more accurate process. No more chasing paperwork. No more guessing if a COI is good enough. Highwire keeps everything moving with tools built for how real projects run.

  • Automatic collection means you stop emailing contractors for missing documents. The system handles it.
  • Smart COI scanning flags missing coverage or policy issues the moment a file comes in.
  • Expiration alerts give you a heads-up before anything lapses, not after.
  • Built-in requirement matching checks coverage against the actual job specs, not just the bare minimum.
  • Live monitoring tracks policy changes, so you’re not blindsided mid-project.

Everything’s designed for construction and industrial teams dealing with real deadlines, real risk, and real consequences.

Manual systems can’t keep up. Highwire does. Ready to stop managing COIs the hard way? See how it works and request a demo today.

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Shayne Gaffney

Highwire, VP, Product & Engineering

Shayne Gaffney is Vice President of Product and Engineering at Highwire, where he leads all software development. With a background in physical therapy and endurance sport coaching, Shayne brings a user-centric approach to building intelligent prequalification and risk mitigation platforms.

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