YC Winter 2026 is officially in the books, and the data is staggering. According to Garry Tan, 14 companies hit the $1M ARR milestone before Demo Day and 10 are raising at over $100M valuations. Rebel Fund’s analysis was even more direct: "No previous batch has come close to this result."

We went through every company in YC's Winter 2026 batch. The thing that kept coming up was Windows. At least 17 of them are automating workflows that still run through Windows desktop software.

That is not a coincidence. Healthcare, financial services, logistics, and field services are some of the largest markets in the economy, and the core systems of record in those industries are thick-client Windows applications. To automate workflows in these systems, an agent needs to operate a real Windows desktop: launch applications, navigate UI, fill out forms, click buttons, and maintain session state when things break. Here are the 17 companies from the batch that will need to do exactly that.

Healthcare

Clinicians work in NextGen, eClinicalWorks, and Dentrix. These are Windows desktop applications.

ClaimGlide: Automates prior authorizations. Many payer submissions still require navigating hospital EHRs behind Citrix wrappers.
Beacon Health: AI employees for primary care that work directly in the EHR for prior auths and referrals. For the long tail of independent clinics, the EHR is legacy desktop software with no cloud API.
Aegis: Automates insurance denial appeals and resubmissions across fragmented legacy payer UIs.
Ruma Care: Automates prior authorizations for infusion clinics across 70+ payer portals, many of which are desktop-bound with no programmatic interface.
Overdrive Health: Medical billing for ambulance agencies. The clearinghouses and dispatch systems in this vertical are Windows-native.
Docura Health: Automates medical record review and report drafting for workers' compensation. The claims management systems evaluators work in are legacy desktop software.

Industrial, Logistics, and Field Services

Equipment dealers, HVAC technicians, and aircraft maintenance teams all close tickets in Windows-native systems of record.

Chasi AI: Revenue engine for equipment dealers. Some of the DMS platforms they plug into are Windows-native with minimal API surface.
Robby: AI documentation for HVAC technicians. Dispatch software for trades is desktop-heavy. Closing a ticket in the system of record means driving the desktop app.
Zymbly: Automates troubleshooting and paperwork for aircraft maintenance technicians. MRO systems like AMOS, Ramco, and TRAX are legacy Windows platforms.

Financial Services, Insurance, and Real Estate

Agency management systems, core banking terminals, and mid-market accounting software are almost all Windows desktop applications.

Alt-X: Real estate underwriting. Their agent turns memos into Excel models and needs desktop access to automate the underwriting flow.
Panta: Commercial insurance brokerage built around AMS platforms like Vertafore. Legacy Windows applications that run the entire industry.
Acolite: AI teammates for insurance agencies that handle submissions, COIs, and SOV mapping across any AMS. Working across these platforms is a desktop automation problem.
Balance: Cloud-first accounting for QBO users. The mid-market runs on QuickBooks Desktop and Sage 50. The bigger market lives on the desktop.
FullSeam: AI employee for finance and accounting teams that logs into a company's accounting, billing, banking, and CRM tools. Same desktop-heavy mid-market.
o11: AI suite integrated into Microsoft 365 for capital markets firms. Turns documents and financial models into a knowledge layer for research, modeling, and client deliverables.
Fenrock AI: AML and BSA compliance for bank back-offices. Core banking terminals and transaction monitoring platforms are almost exclusively Windows-native and often air-gapped from the web.
Oxus: Automates internal audit workflows. Audit at mid-market companies runs on legacy compliance tools that are overwhelmingly Windows-native.

What it takes

Building reliable agents for Windows is an infrastructure problem:

Desktop environments that spin up fast on-demand
Implement computer use controls consistently and reliably across different models
Connecting to a fragmented landscape of legacy protocols, diverse Windows builds, and strict network security layers reliably. Computer use models from Anthropic, Google, and OpenAI have made GUI-level automation viable. The infrastructure to run those models against real Windows environments at production quality is what's missing.

We build that infrastructure at Nen.

If you are a W26 founder or developer building for legacy industries, Nen provides the infrastructure to ship. Book a call with us or join our waitlist.