GitHub Copilot vs Cursor vs Windsurf: Real Talk From Someone Who's Actually Used These in Production

GitHub Copilot Enterprise costs $39/month but that's bullshit - you need GitHub Enterprise Cloud too. Found this out after our first invoice hit $4,200 for 50 devs when I expected $1,950. It's fancy autocomplete that occasionally writes whole functions, usually wrong.

OAuth shit the bed three times last month. Not "degraded performance" - straight up dead. Error: AADSTS50011: The reply URL specified in the request does not match. GitHub support's genius solution? "Have you tried restarting VS Code?" Yeah, that's their fix for everything.

Enterprise features are dashboard theater - pretty charts that tell you "developers used AI suggestions" without telling you if they were any good. Security team likes it because it's Microsoft and they already hate Microsoft, so one more thing doesn't matter.

Cursor is the VS Code fork that makes you feel like a 10x developer until it crashes and takes your unsaved work with it. Happened twice this week on version 0.42.3 with TypeScript files over 2MB. Agent mode is legitimately brilliant - watched it refactor an entire Express router structure in 30 seconds.

Problem is you're completely fucked once you get hooked. Tried going back to regular VS Code after four months of Cursor - felt like trying to code with boxing gloves on. Our procurement team is still having PTSD flashbacks from that $20B Figma deal that Adobe walked away from.

Sales team wouldn't give us enterprise pricing until we sat through three demo calls. Spoiler: starts at $40k minimum for 50+ devs.

Windsurf is what happens when Codeium decides they need an IDE too. Used it for two weeks during our Cursor evaluation. It's... fine? AI suggestions are okay, doesn't crash, doesn't do anything particularly exciting either. $60/month feels like someone saw Cursor's pricing and thought "we can charge that too."

Nobody talks about Windsurf because there's nothing to talk about. It's not broken enough to complain about or good enough to recommend.

Your security team doesn't give a shit about developer productivity. They care about not getting fired when something breaks. Here's what they'll actually ask about.

GitHub Copilot

"Can Microsoft see our code?"

Their lawyers say no. Our security team spent six weeks reading the DPA and came back with "probably not but we can't prove it." Our CISO's exact words: "It's fucking Microsoft, we're already screwed if they want our data."

Has SOC 2 because Microsoft has compliance people. Data stays in the US which screws EU companies. Audit logs show who generated what but not whether it was useful.

Cursor

"Why should we trust a startup with our source code?"

"Privacy Mode" is marketing horseshit. Your code still hits their servers for inference even when they pinky swear not to train on it. Spent 2 fucking hours in a conference room trying to explain this to our security team who kept asking "but where does the code ACTUALLY go?" Like I'm supposed to know their entire infrastructure stack.

No on-prem option killed it for us. Security team exact quote: "Another startup that'll either get acquired by Microsoft or go bankrupt. Hard pass."

Windsurf

"Who?"

Nobody in security has heard of it. That's not automatically bad, but it's not automatically good either.

Reality Check

Happens in healthcare, finance, or defense? You're stuck with GitHub Copilot. Microsoft has the compliance paperwork and our risk team is too lazy to evaluate alternatives. Everyone else gets whatever stops developers from threatening to quit.

Stop reading vendor bullshit. Here's how to choose based on what actually happens when everything goes wrong at 3am.

Start With Your Constraints, Not Your Wishes

If your security team has ever killed a project for "compliance concerns": You're stuck with GitHub Copilot. Period. Spent six weeks evaluating alternatives and security shot down everything that wasn't Microsoft.

If you're already paying the Microsoft tax: Just get GitHub Copilot. You're already fucked, might as well get something useful. Our Microsoft account manager literally said "it's easier to add this than explain why you didn't."

If your developers will actually quit over bad tools: Get Cursor. Only tool I've seen developers genuinely fight for. Just budget for the $78k/year and the inevitable vendor lock-in drama.

If you need something that "just works" across different teams: You're basically choosing between GitHub Copilot's broad compatibility (but Microsoft lock-in) or Cursor's superior experience (but editor lock-in).

The Real Implementation Strategy

Start with a pilot or prepare for disaster. Picked 30 developers for 90 days. Made the stupid mistake of mentioning it to our VP who immediately started asking for "quantified productivity gains" after week fucking 1. Like I'm supposed to have ROI metrics for people learning a new tool.

Don't measure lines of code. Found out the hard way when developers started generating 500-line comments to boost their metrics.

What to actually track:

• Do people turn the extension on?
• Do they stop complaining about boilerplate code?
• Do code reviews catch fewer basic syntax errors?
• Do junior developers ask fewer "how do I write a for loop" questions?

Plan for resistance. Half your team will hate any change. Senior developers will complain it makes code worse. Junior developers will become dependent. Security will find new concerns every month. This is normal.

Budget for Reality

Direct costs: $60+ per dev per month
Hidden costs:

• Security reviews take forever
• Developers need time to learn new workflows
• Support tickets when OAuth breaks again
• Contract negotiations

This shit gets expensive fast, especially in the first year.

What Success Actually Looks Like

These tools don't magically turn junior devs into senior architects. They just eliminate some of the tedious copy-paste bullshit and catch stupid typos.

If your development process is broken - slow reviews, unclear requirements, terrible testing - AI tools won't fix that. They'll just add new ways to create bugs.

Good outcomes:

• Faster boilerplate code
• Fewer copy-paste errors
• Junior developers learning faster
• Less googling "how to iterate array javascript"

Bad outcomes:

• Developers fighting about AI-generated code quality
• New security vulnerabilities nobody knows how to catch
• Locked into tools you can't easily switch from

Pick What Won't Fuck You Later

GitHub Copilot: Boring, expensive, works most of the time. Safe choice that nobody will blame you for.

Cursor: Amazing when it works, expensive as hell, locks you into their editor forever. Choose this if you trust startups with your career.

Windsurf: Don't.

Choose based on whether you'd rather explain why you spent $78k on Cursor or why GitHub Copilot OAuth broke again.