I've been through this rodeo three times now. Here's what actually happens when you try to get AI coding tools approved by enterprise IT.
The difference between Windsurf and Cursor isn't about features - both work fine. It's about whether your security team will let you sleep at night.
Windsurf: "We Can Run On Your Servers"
Windsurf's enterprise strategy boils down to three options, each with their own special flavor of pain:
Cloud Deployment - Your code goes to their servers. Sounds scary but it's SOC 2 Type II compliant and they promise not to keep it. Most security teams can live with this, especially when they see the encryption standards and access controls they use.
Hybrid Deployment - Sensitive code stays put, AI calls go out. This sounds perfect until you realize you're now debugging network issues between your VPC and their APIs. I've seen this setup work well for defense contractors and healthcare orgs that need compliance without going full paranoid.
Self-Hosted Deployment - Everything runs in your data center. Your security team loves it. Your DevOps team hates it. This is the only way to get FedRAMP High authorization, which matters if you're selling to the government.
What actually happened: Deployed Windsurf self-hosted for a fintech client who wanted "bank-level security." 14 weeks later, we had it working. First three deployments failed with some DNS timeout error that Google couldn't explain - took hiring a $450/hour consultant to point out our proxy config was "non-standard" (aka fucked).
We budgeted $45k for infrastructure. Final cost was $85k because nobody mentioned we'd need a dedicated certificate authority and custom monitoring setup. Worth it though - compliance team stopped asking stupid questions about "where does our code go?"
Cursor: "Just Use Our Cloud"
Cursor's approach is dead simple: everything runs in their cloud, take it or leave it. Their recent pricing changes added usage controls, but you still need someone watching the billing dashboard constantly.
The good: Deploy fast, infrastructure just works.
The bad: Your code leaves your building. Deal with it.
The ugly: When Cursor breaks, your entire engineering team goes home early.
Privacy Mode doesn't train their models on your code, but it's still getting processed on their servers. Some security teams can live with this after reading their data policies. Others hear "cloud processing" and start hyperventilating.
What actually happened: 200-person startup went live with Cursor in 3 weeks. Developers loved it until Cursor had a 4-hour outage during our sprint deadline with zero useful error messages - just "SERVICE_UNAVAILABLE" for 4 hours straight. Suddenly everyone remembered why we used to have local dev environments.
Monthly bills ranged from $11k to $24k depending on whether someone discovered a new AI feature. The usage analytics help, but predicting developer behavior is like predicting the weather - you're gonna be wrong.
The Compliance Reality Check
Both platforms have SOC 2 Type II certification (big whoop, everyone has that now), but that's where the similarity ends:
Windsurf wins the compliance game with FedRAMP High authorization - if you need to sell to government agencies, this is your only choice. Their self-hosted option lets you check every paranoid compliance box your security team can think of.
Cursor keeps it simple - their compliance controls are built-in and automatically updated. You don't need to worry about security patches or maintaining compliance infrastructure. It's all managed for you.
Windsurf dumps all the work on you but you control everything. Cursor handles the messy stuff but you're fucked if they screw up.
The Money Talk
Windsurf Enterprise costs $60/user/month with 1,000 credits per user. Simple enough. Most teams don't hit the credit limit, so budgeting is straightforward.
Cursor's usage-based billing will fuck your budget sideways. $40/user/month sounds reasonable until your team discovers AI autocomplete and your bill jumps 300%. I've seen monthly costs swing from $8k to $31k for the same team just because they shipped a big feature and used more AI suggestions.
Their pricing calculator is about as accurate as weather forecasting. Estimate $12k/month, budget for $25k, and pray your developers don't all decide to refactor legacy code in the same week.
Scaling Your Team (Without Breaking the Bank)
Windsurf hits you with a 200-user limit on their Teams plan, then forces you to Enterprise pricing. It's annoying, but the Enterprise features (better security, deployment options) usually justify the cost jump.
Cursor scales infinitely - you pay for what you use. Great for companies where only half your developers actually need AI help. Sucks when your entire team discovers AI coding and your bill triples overnight.
Cursor's admin API gives you detailed usage analytics. Windsurf's admin tools are basic as hell - they assume you'll integrate with your existing systems.
The deployment reality: Cursor takes 2-3 weeks to roll out. Windsurf cloud deployments are similar, but self-hosted? Plan for 8-16 weeks and at least one mental breakdown from your DevOps team.
Bottom Line: Both platforms work. Windsurf gives you control at the cost of complexity. Cursor gives you simplicity at the cost of vendor dependency.
Most enterprises already know which trade-off they can live with based on their regulatory environment and risk tolerance.
