You've got a 500-file JavaScript codebase that should be TypeScript. Traditional migration advice says "just convert one file at a time" which is like suggesting you eat an elephant with a teaspoon. I've seen migration horror stories where developers rage-quit after three months of manually adding type annotations to event handlers that should've been obvious.
What Actually Works in 2025
AI tools have gotten scary good at TypeScript migration. I migrated our 200-file React app last month. Took a weekend and maybe $50 in API calls - way cheaper than hiring a consultant. That includes all the time spent figuring out why Cline kept adding any
types to React event handlers. The official migration docs still assume manual conversion, but AI tools changed the game completely.
What makes this year different:
- AI tools actually understand context now - Cursor reads your entire codebase, Cline runs workflows without fucking up, and Claude Code handles complex business logic
- TypeScript 5.7 (released in late 2024) has improvements for migration projects like better error messages and smarter type inference
- Workflow automation that doesn't make you want to throw your laptop out the window
- API costs dropped - competition drove prices down, making large migrations actually affordable
What Changed
The old way of migration sucked: plan everything perfectly upfront, convert files one at a time, manually fix every TypeScript compiler error, cry internally when you realize you made architecture decisions that don't work with strict mode.
The new way sucks less: set up workflows once, let AI do the grunt work, review the output like you're code reviewing a junior dev who's really eager but occasionally thinks every function parameter should be any
. Expect to spend a day fixing React event handlers because AI keeps generating onChange: (e: any) => void
instead of onChange: (e: ChangeEvent<HTMLInputElement>) => void
.
Our "quick migration" turned into a 3-week nightmare until I figured out the build optimizations. Build times went to shit initially - like 4x slower. Took a few days of config tweaking to get back to reasonable speeds.
Why TypeScript Structure Makes AI Less Stupid
After migrating a bunch of codebases, here's what I learned: TypeScript gives AI something to work with. When you have actual type definitions instead of // TODO: figure out what this parameter is supposed to be
, AI can understand your code better than you do. The type system provides context that helps AI make better suggestions instead of just guessing.
It's a decent feedback loop:
- AI helps migrate to TypeScript (adding structure to your chaos)
- TypeScript structure makes AI suggestions suck less
- Less terrible AI suggestions means you don't spend 3 hours debugging why
user.id
is suddenlystring | undefined
Tools That Won't Make You Regret Everything
After trying every tool that claims to help with TypeScript migration, here's what doesn't completely suck:
Tools that actually work:
- Cline - VS Code extension that runs autonomously. Best for "migrate this entire folder while I get coffee". Warning: it will add
any
types to everything and you'll spend a day fixing them. I've seen it convertfunction handleClick(event)
tofunction handleClick(event: any)
instead of the obviousMouseEvent<HTMLButtonElement>
. Gets it wrong every time. - Cursor - AI-first IDE that's surprisingly decent. Their TypeScript migration suggestions are better than mine, which hurts my ego but saves time.
- Claude Code - For when you need to explain why your 500-line function should stay a 500-line function and the AI should just add types, not refactor everything.
Old-school but useful:
- ts-migrate - Airbnb's tool from before AI was good. Still useful for "make everything compile first, fix types later". It adds
any
everywhere, but at least your build won't fail. Expect errors likeTS7006: Parameter 'props' implicitly has an 'any' type
on literally every React component. - ts-morph - For when you need to write your own migration scripts because your codebase has 47 different ways to handle API responses.
Don't just pick one tool and pray. The successful migrations I've seen use 2-3 tools in sequence - start broad with ts-migrate, then let AI fix the obvious stuff, then cry over the edge cases.
Recent TypeScript Improvements for Migration
TypeScript 5.7 (released late 2024) has some decent improvements for migration projects:
Better Project Initialization:
## Recent TypeScript creates sane defaults instead of 50 lines of commented garbage
npx tsc --init
## Creates a tsconfig.json that actually works instead of breaking everything
## No more "strict mode will make you hate TypeScript" surprises
Smarter Error Messages:
// Error messages are slightly less cryptic now
// Still not great, but better than "Type 'never' is not assignable to type 'string'"
function getUser(userId: string) { /* ... */ }
// getUser(userID); // Now gives better context about the typo
Improved Type Inference:
// Better type narrowing in newer versions
const config = {
apiUrl: "https://api.example.com",
timeout: 5000
} satisfies Record<string, string | number>;
// TypeScript is smarter about inferring the actual types here
The Cost-Benefit Reality Check
Let's talk actual numbers based on 2025 migration experiences:
Traditional Manual Migration (1000-file project):
- Time: 3-6 months (if you don't quit first)
- Developer cost: Whatever your sanity is worth
- Risk: High (I've seen teams abandon half-migrated codebases)
- Result: You'll miss obvious stuff because you're burned out
AI-Assisted Migration (1000-file project):
- Time: 2-4 weeks (plus another week fixing the AI's mistakes)
- AI API cost: Could be a few hundred in API calls depending on usage (check current pricing)
- Developer cost: Your dignity when you realize the AI is better at this than you
- Risk: Low (iterative approach means you can always fix stuff later)
- Result: Consistently decent, though you'll still need to fix the React event handlers manually
Even if you blow money on API calls, it beats manually converting function(event)
to function(event: React.FormEvent<HTMLFormElement>)
thousands of times. I spent half a day just figuring out why onClick={(e) => handleSubmit(e)}
was throwing TS2345: Argument of type 'MouseEvent' is not assignable to parameter of type 'FormEvent'
.
When AI Migration Makes the Most Sense
Perfect candidates for AI-assisted migration:
- Codebases 20-5000+ files (sweet spot for AI efficiency)
- Projects with existing patterns (AI can learn and replicate)
- Teams comfortable with iterative approaches (not perfectionism)
- TypeScript-curious developers (motivated to learn)
When to consider traditional approaches:
- Tiny projects (<20 files - faster to do manually)
- Highly unique domain logic (AI training data lacks context)
- Teams with zero TypeScript experience (need educational value of manual work)
Setting Realistic Expectations
AI-assisted migration isn't magic. Here's what to expect:
What AI does excellently:
- Bulk file renaming and basic type annotations
- Pattern recognition and replication
- Boilerplate generation
- Consistency across large codebases
What requires human oversight:
- Complex type relationships and generics (AI loves generating
T extends Record<string, unknown>
for everything) - Domain-specific business logic types (AI doesn't know your API returns
userId
as string sometimes, number other times) - Performance optimization decisions (AI will happily generate 47 nested generic types that tank your build)
- Team coding standards (unless you want every interface named
IWhatever
)
The goal isn't to have AI do everything perfectly - it's to have AI handle 80-90% of the tedious work so humans can focus on the interesting, high-value decisions that actually matter.
This guide shows you how to set up these workflows, which tools to use when, and how to migrate without losing your shit.