Look, I'm going to tell you about the time I watched a perfectly functional 15-person engineering team light $40k on fire switching from GitHub Copilot to Cursor. The CTO read some bullshit article about "10x developer productivity" and decided we needed to "optimize our toolchain."
The math looked simple enough: GitHub Copilot Business was costing us $285/month ($19 × 15 devs). Cursor Pro would be $300/month ($20 × 15 devs), so basically the same. "We'll get better multi-file editing for essentially free," the CTO said. What could go wrong?
Everything. Everything went wrong.
Week 1: The Honeymoon Ends Fast
First day with Cursor and our CI/CD pipeline starts throwing errors. Turns out Cursor's VS Code fork doesn't play nice with our custom ESLint configurations. The kind of shit that works fine with regular VS Code but breaks in weird ways with Cursor's modifications.
Error message that ruined my Tuesday:
ERROR: Unable to load configuration file eslint.config.js
Module resolution failed for @company/eslint-config
Spent 6 hours debugging what should have been a 5-minute switch. Cursor's documentation says it's "VS Code compatible" but doesn't mention the fork breaks certain extension loading patterns. Three developers were basically useless that first week while we figured out toolchain compatibility issues.
The Muscle Memory Problem Nobody Talks About
Here's what actually killed our productivity: GitHub Copilot had trained us to code a specific way. We'd gotten used to its autocomplete patterns, the way it handled context, how it suggested function names. Cursor works differently enough that your fingers type Tab expecting Copilot-style completions and get confused when Cursor suggests something else.
The real learning curve looked like this:
- Week 1: Developers actively fighting the tool, productivity in the toilet
- Week 2-3: Still reaching for Copilot shortcuts that don't exist in Cursor
- Week 4-6: Finally adapting but moving slower than before migration
- Week 7-8: Getting back to baseline productivity
- Week 9+: Maybe, possibly better than before (if you're lucky)
We budgeted for "a couple days of adjustment." Three months later, we were still dealing with developers who'd randomly switch back to regular VS Code when deadlines got tight because they could move faster without any AI tool than fumbling through Cursor's different approach.
The Costs That Blindsided Us
1. The Time Sink of Retraining Developers
We lost 3-4 hours per developer per week for the first month just answering questions about "how do I do X in Cursor that I used to do in Copilot?" Senior devs became unpaid support agents instead of coding. Our most productive developer spent an entire day helping others figure out Cursor's multi-file editing because it works completely differently than expected.
2. Configuration Hell That Never Ends
Every developer had slightly different VS Code configurations. Cursor's fork meant we had to rebuild workspace settings, figure out which extensions worked (spoiler: not all of them), and deal with random compatibility issues. Our devtools setup that took 5 minutes with regular VS Code took 2 hours per person with Cursor.
Real gotcha that bit us: Cursor's workspace settings don't sync the same way as VS Code. Developers kept losing their configurations when switching machines or updating Cursor.
3. Cursor's Credit System Is Designed to Fuck You
That $20/month turns into $45-60/month real quick when you actually use the tool. Cursor's credit consumption is unpredictable as hell. One developer doing a large refactor burned through two months of credits in a week. No warning, no throttling, just a surprise $120 bill.
The worst part? You can't set spending limits. It's like they want you to accidentally exceed your budget.
4. All the Administrative Bullshit You Don't Think About
- Coordinating the GitHub Copilot cancellation (harder than it sounds)
- Getting everyone signed up for Cursor accounts (took two weeks)
- Updating our security policies because now we're sending code to a different vendor
- Figuring out which licenses to buy (Pro vs Enterprise features are confusing)
- Dealing with billing questions when credits start disappearing faster than expected
The Few Cases Where Migration Doesn't Suck
Look, I'm not going to lie and say migration is always wrong. But the teams that don't regret it have very specific reasons that make the pain worth it.
1. You Have a Technical Need That Copilot Can't Meet
- Air-gapped environments: If you legally can't send code to Microsoft's servers, Tabnine Enterprise is your only real option
- Specific AI model requirements: Maybe you need Claude-3.5 specifically for domain-specific code and Copilot's models aren't cutting it
- Multi-file refactoring at scale: Large legacy codebases where Cursor's multi-file editing actually provides measurable time savings
2. Your Developers Actually Drove the Decision
The migrations that work are developer-led, not manager-imposed. When 3-4 senior developers come to you with a specific tool recommendation and can demonstrate concrete improvements on real work (not demos), that's different from "the CEO read a blog post."
3. You Actually Budgeted for Reality
Teams that don't get burned budget 3-5x the subscription cost difference and plan for 6-12 months before expecting positive ROI. They treat migration like any other major engineering initiative: expensive, disruptive, and requiring dedicated resources.
Questions to Ask Before You Fuck Up Your Engineering Velocity
Is Copilot actually the problem?
Half the time, teams think Copilot sucks when really their code is poorly structured, their prompts are garbage, or they haven't figured out how to use it effectively. If your developers are fighting with autocomplete, the issue might be code quality, not the AI tool.
What specific thing can't Copilot do that you need?
- Multi-file refactoring: Cursor is legitimately better here for large-scale changes
- Terminal-native workflow: Claude Code integrates with shell better
- Air-gapped deployment: Tabnine Enterprise is your only option
- Custom model training: If you need domain-specific fine-tuning
Are you prepared to double productivity to justify migration costs?
Our migration cost us roughly 40 hours of developer time per person plus ongoing productivity loss. To break even within a year, the new tool needs to make developers twice as productive in specific areas. Not 10% better. Double.
Do you have executive backing and realistic budget?
If your CTO isn't personally committed to seeing this through and you haven't budgeted for 3-4x the subscription cost difference, don't start.
Why Tool Hopping Kills Teams
Here's what I've seen happen: teams switch from Copilot to Cursor, get frustrated with credit overages, try Claude Code, hate the terminal workflow changes, then end up back on Copilot after wasting 6 months and $30k.
Every tool switch resets your team's muscle memory and productivity. The most productive teams I know picked a tool and got really good at it instead of constantly evaluating "better" options.
GitHub Copilot has one massive advantage: it's boring and stable. Microsoft isn't going to run out of money, shut down the service, or dramatically change pricing models. That stability is worth more than the marginal improvements promised by smaller tools.
The brutal truth: Most AI coding tools are good enough for 90% of use cases. The productivity gains from switching tools are almost always smaller than the productivity losses from migration disruption. Focus on shipping products, not optimizing your development tools.
