diff --git a/Dockerfile b/Dockerfile
index a3372357..4d102664 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,3 +1,10 @@
+# Pre-generate OpenAPI specs from the stripe/openapi repo
+FROM node:24-alpine AS spec-builder
+RUN apk add --no-cache git
+RUN git clone --filter=blob:none https://github.com/stripe/openapi /stripe-openapi
+COPY packages/openapi/scripts/generate-all-specs.mjs /generate-all-specs.mjs
+RUN node /generate-all-specs.mjs /stripe-openapi /generated-specs
+
 # Install deps and create standalone deployment
 # Expects pre-built dist/ directories in the build context (from `pnpm build`)
 FROM node:24-alpine AS build
@@ -9,6 +16,7 @@ RUN corepack enable
 
 WORKDIR /app
 COPY . ./
+COPY --from=spec-builder /generated-specs ./packages/openapi/generated-specs
 
 RUN --mount=type=cache,id=pnpm,target=/pnpm/store pnpm install --frozen-lockfile
 RUN pnpm --filter @stripe/sync-engine deploy --prod /deploy
diff --git a/packages/openapi/bundled-spec.json b/packages/openapi/latest-spec.json
similarity index 100%
rename from packages/openapi/bundled-spec.json
rename to packages/openapi/latest-spec.json
diff --git a/packages/openapi/package.json b/packages/openapi/package.json
index 168c083e..d9b48958 100644
--- a/packages/openapi/package.json
+++ b/packages/openapi/package.json
@@ -11,7 +11,7 @@
     }
   },
   "scripts": {
-    "build": "tsc && cp bundled-spec.json dist/bundled-spec.json",
+    "build": "tsc && cp latest-spec.json dist/latest-spec.json && (cp -r generated-specs dist/generated-specs 2>/dev/null || true)",
     "test": "vitest --passWithNoTests"
   },
   "files": [
diff --git a/packages/openapi/scripts/generate-all-specs.mjs b/packages/openapi/scripts/generate-all-specs.mjs
new file mode 100644
index 00000000..d5076f42
--- /dev/null
+++ b/packages/openapi/scripts/generate-all-specs.mjs
@@ -0,0 +1,59 @@
+#!/usr/bin/env node
+import { execSync } from 'node:child_process'
+import { writeFileSync, mkdirSync } from 'node:fs'
+import { join } from 'node:path'
+
+const [repoPath, outputDir] = process.argv.slice(2)
+if (!repoPath || !outputDir) {
+  console.error('Usage: node generate-all-specs.mjs <repoPath> <outputDir>')
+  process.exit(1)
+}
+
+const execOpts = { encoding: 'utf8', stdio: ['pipe', 'pipe', 'pipe'] }
+
+let log
+try {
+  log = execSync(
+    `git -C ${repoPath} log --format="%H" -- latest/openapi.spec3.sdk.json openapi/spec3.json`,
+    execOpts
+  )
+} catch (err) {
+  console.error(`Fatal: cannot access repo at ${repoPath}: ${err.message}`)
+  process.exit(1)
+}
+
+const shas = log.trim().split('\n').filter(Boolean)
+mkdirSync(outputDir, { recursive: true })
+
+const seen = new Map()
+const paths = ['latest/openapi.spec3.sdk.json', 'openapi/spec3.json']
+
+for (const sha of shas) {
+  let raw = null
+  for (const p of paths) {
+    try {
+      raw = execSync(`git -C ${repoPath} show ${sha}:${p}`, execOpts)
+      break
+    } catch {
+      // file doesn't exist at this path for this commit
+    }
+  }
+  if (!raw) continue
+
+  let version
+  try {
+    version = JSON.parse(raw).info?.version
+  } catch {
+    continue
+  }
+  if (!version || seen.has(version)) continue
+
+  const filename = `${version}.json`
+  writeFileSync(join(outputDir, filename), raw)
+  seen.set(version, filename)
+  console.error(`Generated ${version}`)
+}
+
+const manifest = Object.fromEntries(seen)
+writeFileSync(join(outputDir, 'manifest.json'), JSON.stringify(manifest, null, 2) + '\n')
+console.error(`Done: ${seen.size} specs from ${shas.length} commits`)
diff --git a/packages/openapi/specFetchHelper.ts b/packages/openapi/specFetchHelper.ts
index d6caaccf..81785458 100644
--- a/packages/openapi/specFetchHelper.ts
+++ b/packages/openapi/specFetchHelper.ts
@@ -5,6 +5,7 @@ import { fileURLToPath } from 'node:url'
 import type { OpenApiSpec, ResolveSpecConfig, ResolvedOpenApiSpec } from './types.js'
 
 const DEFAULT_CACHE_DIR = path.join(os.tmpdir(), 'stripe-sync-openapi-cache')
+const GENERATED_SPECS_DIR = fileURLToPath(new URL('./generated-specs', import.meta.url))
 
 // CDN mirror of the official Stripe REST API specs (from github.com/stripe/openapi).
 // Served from stripe-sync.dev — no auth, no GitHub rate limits.
@@ -14,8 +15,8 @@ const STRIPE_SPEC_CDN_BASE_URL =
   process.env.STRIPE_SPEC_CDN_BASE_URL ?? 'https://stripe-sync.dev/stripe-api-specs'
 
 // The spec bundled into this package at build time.
-// Update this constant and bundled-spec.json together when bumping.
-export const BUNDLED_API_VERSION = '2026-03-25.dahlia'
+// Update this constant and latest-spec.json together when bumping.
+export const LATEST_BUNDLED_API_VERSION = '2026-03-25.dahlia'
 
 export async function resolveOpenApiSpec(
   config: ResolveSpecConfig,
@@ -40,14 +41,25 @@ export async function resolveOpenApiSpec(
 
   // If the requested version matches what's bundled, serve from the filesystem
   // without any network calls or caching overhead.
-  if (extractDatePart(apiVersion) === extractDatePart(BUNDLED_API_VERSION)) {
-    const bundledPath = fileURLToPath(new URL('./bundled-spec.json', import.meta.url))
-    const spec = await readSpecFromPath(bundledPath)
+  if (extractDatePart(apiVersion) === extractDatePart(LATEST_BUNDLED_API_VERSION)) {
+    const latestPath = fileURLToPath(new URL('./latest-spec.json', import.meta.url))
+    const spec = await readSpecFromPath(latestPath)
     return {
       apiVersion,
       spec,
       source: 'bundled',
-      cachePath: bundledPath,
+      cachePath: latestPath,
+    }
+  }
+
+  // Try pre-generated specs from the generated-specs directory (built at Docker image time).
+  const preGenSpec = await tryLoadPreGeneratedSpec(apiVersion)
+  if (preGenSpec) {
+    return {
+      apiVersion,
+      spec: preGenSpec.spec,
+      source: 'bundled',
+      cachePath: preGenSpec.path,
     }
   }
 
@@ -99,6 +111,42 @@ export async function resolveOpenApiSpec(
   }
 }
 
+// Module-scope manifest cache: undefined = not yet tried, null = tried and missing
+let generatedSpecManifest: { [version: string]: string } | null | undefined = undefined
+
+async function tryLoadPreGeneratedSpec(
+  apiVersion: string
+): Promise<{ spec: OpenApiSpec; path: string } | null> {
+  try {
+    if (generatedSpecManifest === null) return null
+
+    if (generatedSpecManifest === undefined) {
+      try {
+        const manifestRaw = await fs.readFile(
+          path.join(GENERATED_SPECS_DIR, 'manifest.json'),
+          'utf8'
+        )
+        generatedSpecManifest = JSON.parse(manifestRaw) as { [version: string]: string }
+      } catch {
+        generatedSpecManifest = null
+        return null
+      }
+    }
+
+    const requestedDate = extractDatePart(apiVersion)
+    const matchedKey = Object.keys(generatedSpecManifest).find(
+      (key) => extractDatePart(key) === requestedDate
+    )
+    if (!matchedKey) return null
+
+    const specPath = path.join(GENERATED_SPECS_DIR, generatedSpecManifest[matchedKey])
+    const spec = await readSpecFromPath(specPath)
+    return { spec, path: specPath }
+  } catch {
+    return null
+  }
+}
+
 async function readSpecFromPath(openApiSpecPath: string): Promise<OpenApiSpec> {
   const raw = await fs.readFile(openApiSpecPath, 'utf8')
   let parsed: unknown