Read initial Enterprise readiness and security reports for:
Cursor: https://harini.blog/2025/05/07/detailed-security-and-enterprise-readiness-report-cursor-ai-ide/
Windsurf: https://harini.blog/2025/07/02/windsurf-detailed-enterprise-security-readiness-report/
AI Coding Assistants — Enterprise-Readiness Snapshot for Healthcare Orgs
Audience: CISO / VP-Engineering / Head of AI
Scope: Comparison of Windsurf™ (formerly Codeium) vs Cursor for a U.S. healthcare-regulated environment that handles PHI and must satisfy HIPAA, SOC 2, and (ideally) FedRAMP controls.
1 Executive-level takeaway
| Windsurf | Cursor | |
|---|---|---|
| Overall fit for a HIPAA/FedRAMP healthcare org | ✅ Ready-today – FedRAMP High accredited; HIPAA-capable with BAA; Hybrid & Self-Hosted tiers keep code inside our tenant. | ⚠️ Limited – SOC 2 Type II only; cloud-only on AWS; no BAA/HIPAA controls; zero-retention depends on user-side Privacy Mode toggle. |
| Recommendation | Proceed to 4-week Hybrid POC. | Keep under observation for less-regulated teams; not suitable for PHI-adjacent work without major compensating controls. |
2 Side-by-side detail
| Category | Windsurf | Cursor | Why it matters |
|---|---|---|---|
| Certifications / attestations | SOC 2 Type II + FedRAMP High; HIPAA alignment & BAA on request. (windsurf.com) | SOC 2 Type II only. (cursor.com) | FedRAMP & HIPAA are hard requirements for many healthcare workloads. |
| Deployment models | Cloud, Hybrid (code+embeddings in our VPC, GPU inference in Windsurf cloud), Self-Hosted (air-gapped K8s/Compose). (windsurf.com) | Cloud-only on AWS; no VPC-peered or on-prem option. (cursor.com) | Self-host/Hybrid keeps any potential PHI fully resident. |
| Default data-retention posture | Zero-retention on by default for paid org seats; remote-indexing & web-search are opt-in. (windsurf.com) | Zero-retention only when each user or admin enables Privacy Mode; otherwise code snippets can persist. (forum.cursor.com, cursor.com) | Operational risk if developers forget to toggle privacy. |
| Sub-processors that see code | GCP, Crusoe, Oracle, Palantir + AWS GovCloud, OpenAI, Anthropic, Vertex, xAI, Fireworks, Bing (opt-in). All but Bing under zero-retention DPAs. (windsurf.com) | AWS, Cloudflare, Azure, GCP, Fireworks, OpenAI, Anthropic, Vertex, xAI, Turbopuffer, Exa, SerpAPI (web), Bing search. Zero-retention dependent on Privacy Mode; Turbopuffer stores embeddings. (cursor.com) | Longer vendor chain ⇒ larger audit surface. |
| HIPAA controls | Declares HIPAA compliance; BAA available. (windsurf.com) | No HIPAA claim; forum indicates not yet positioned for PHI workloads. | Needed for any code that manipulates PHI (data-pipelines, ETL, etc.). |
| Agent safety | Cascade agent requires explicit approval before risky terminal actions; admin can disable web/Bing. (windsurf.com) | Cursor Tab & Chat only; no multi-step agent yet (risk surface smaller). (cursor.com) | Human-in-loop guardrails critical for prod branches. |
| Audit & Admin | SAML SSO, RBAC, per-seat model toggles, on-tenant audit logs (Hybrid / Self-Hosted). (windsurf.com) | SAML SSO via WorkOS; audit data retains on Cursor cloud; no customer-side log storage. (cursor.com) | Centralized logs ease SOX & HIPAA audits. |
| On-going roadmap gaps | Self-Hosted lacks Cascade today. | No self-host; no single-tenant option; workspace-trust disabled by default. (cursor.com) | Evaluate agent parity vs. security envelopes. |
3 Risk matrix (health-sector lens)
| Risk | Windsurf | Cursor |
|---|---|---|
| PHI spillage outside org boundary | Hybrid/Self-Hosted keep code & embeddings in-tenant; zero-retention default for model vendors. | Cloud-only; privacy mode off = 30-day provider logs; risk of devs forgetting toggle. |
| Regulator scrutiny (OCR, HHS) | FedRAMP High controls map >75 % to HIPAA §164.*; BAA available. | Only SOC 2; would need compensating controls & lawyered DPA. |
| Agentic code execution | Human approval for terminal commands; unsafe ops disabled Org-wide. | No agent; simpler surface but fewer controls. |
| Vendor sprawl | 11 code-seeing providers (all but Bing zero-retention). | 18+ code-seeing providers; Turbopuffer & web-search pair add storage/search vectors. |
| Data-residency (EU/US Gov) | EU Frankfurt cluster; AWS GovCloud via Palantir FedStart. | US-only AWS multitenant. |
4 Recommended next steps
- Run a 4-week Windsurf Hybrid pilot
- Scope: non-production repos that process synthetic or de-identified clinical data.
- Measure: velocity uplift, agent safety incident rate, SIEM log integration ease.
- Require BAA & FedRAMP attestation pack
- Request full audit artifacts (SOC 2 report, FedRAMP SSP, latest pen-test).
- Draft internal “AI Coding Policy”
- Blanket rule: privacy/zero-retention always on; web/Bing search disabled unless InfoSec approves.
- Mandate SAST/DAST and peer-review gates on AI-generated commits.
- Keep Cursor on the radar for front-end or low-risk components where PHI never flows.
- Ask Cursor for roadmap on VPC or self-host; confirm potential HIPAA stance.
5 Decision memo (one-liner)
Select Windsurf Hybrid as the primary AI coding assistant for HIPAA-regulated development; revisit Cursor when it offers self-host or HIPAA-compliant VPC support.
Infinite Couch 