diff --git a/config/scripts/rebuild-native-deps.mjs b/config/scripts/rebuild-native-deps.mjs
index bb0d8707d..3e73aafdd 100644
--- a/config/scripts/rebuild-native-deps.mjs
+++ b/config/scripts/rebuild-native-deps.mjs
@@ -20,10 +20,12 @@
  */
 
 import { rebuild } from '@electron/rebuild'
-import { execFileSync } from 'node:child_process'
+import { execFileSync, spawnSync } from 'node:child_process'
+import { createRequire } from 'node:module'
 import { existsSync, globSync, readFileSync, writeFileSync } from 'node:fs'
 import { resolve } from 'node:path'
 
+const require = createRequire(import.meta.url)
 const projectDir = process.cwd()
 const electronVersion = JSON.parse(
   readFileSync(resolve(projectDir, 'node_modules/electron/package.json'), 'utf8')
@@ -41,6 +43,23 @@ if (ignoreModules.length > 0) {
 // ABI regardless of the package manager's store layout.
 const NATIVE_MODULES = ['better-sqlite3', 'node-pty', 'cpu-features']
 const onlyModules = NATIVE_MODULES.filter((m) => !ignoreModules.includes(m))
+const forceRebuild = process.env.ORCA_FORCE_NATIVE_REBUILD === '1'
+
+if (!forceRebuild) {
+  // Why: Windows cannot unlink a loaded .node DLL, so avoid @electron/rebuild
+  // when the current install already works with Electron's ABI.
+  const probe = probeElectronNativeModules(onlyModules)
+  if (probe.ok) {
+    console.log('[rebuild] Native modules already load in Electron; skipping rebuild.')
+    process.exit(0)
+  }
+  console.log('[rebuild] Native modules do not load in Electron; rebuilding.')
+  if (probe.stderr.trim()) {
+    console.log(probe.stderr.trim())
+  }
+} else {
+  console.log('[rebuild] ORCA_FORCE_NATIVE_REBUILD=1 set; forcing native rebuild.')
+}
 
 // Why: cpu-features ships without `buildcheck.gypi`; its own `install` script
 // generates it by running `node buildcheck.js > buildcheck.gypi` before
@@ -49,10 +68,9 @@ const onlyModules = NATIVE_MODULES.filter((m) => !ignoreModules.includes(m))
 // store prune, or a prior failed run) node-gyp aborts with
 // "buildcheck.gypi not found". Regenerate it here before rebuilding.
 if (!ignoreModules.includes('cpu-features')) {
-  const cpuFeatureDirs = globSync(
-    'node_modules/.pnpm/cpu-features@*/node_modules/cpu-features',
-    { cwd: projectDir },
-  )
+  const cpuFeatureDirs = globSync('node_modules/.pnpm/cpu-features@*/node_modules/cpu-features', {
+    cwd: projectDir
+  })
   for (const relDir of cpuFeatureDirs) {
     const dir = resolve(projectDir, relDir)
     const gypiPath = resolve(dir, 'buildcheck.gypi')
@@ -62,15 +80,12 @@ if (!ignoreModules.includes('cpu-features')) {
     try {
       const out = execFileSync(process.execPath, ['buildcheck.js'], {
         cwd: dir,
-        encoding: 'utf8',
+        encoding: 'utf8'
       })
       writeFileSync(gypiPath, out)
       console.log(`[rebuild] Generated ${relDir}/buildcheck.gypi`)
     } catch (/** @type {any} */ err) {
-      console.error(
-        `[rebuild] Failed to generate ${relDir}/buildcheck.gypi:`,
-        err?.message ?? err,
-      )
+      console.error(`[rebuild] Failed to generate ${relDir}/buildcheck.gypi:`, err?.message ?? err)
       process.exit(1)
     }
   }
@@ -87,9 +102,121 @@ try {
     // (e.g., system Node instead of Electron's embedded Node). This is
     // common after pnpm install, which compiles native modules for system
     // Node before postinstall runs this script.
-    force: true,
+    force: true
   })
 } catch (/** @type {any} */ err) {
   console.error('[rebuild] Native module rebuild failed:', err?.message ?? err)
+  if (isWindowsNativeLockError(err)) {
+    console.error(
+      '[rebuild] A Windows process appears to be using a native .node file. ' +
+        'Close running Orca/Electron/dev processes for this worktree, then rerun `pnpm install` ' +
+        'or `pnpm run rebuild:electron`.'
+    )
+    if (isPostinstall() && process.env.ORCA_STRICT_NATIVE_REBUILD !== '1') {
+      console.error(
+        '[rebuild] Continuing postinstall because the failure is a Windows file lock. ' +
+          'The next dev/start command will re-check native modules.'
+      )
+      process.exit(0)
+    }
+  }
   process.exit(1)
 }
+
+function probeElectronNativeModules(moduleNames) {
+  let electronExecutable
+  try {
+    electronExecutable = require('electron')
+  } catch (error) {
+    return { ok: false, status: null, stderr: formatError(error) }
+  }
+
+  const probeSource = `
+const { createRequire } = require('node:module')
+const { release } = require('node:os')
+const { resolve } = require('node:path')
+const projectRequire = createRequire(resolve(process.cwd(), 'package.json'))
+const moduleNames = ${JSON.stringify(moduleNames)}
+const failures = []
+
+for (const moduleName of moduleNames) {
+  try {
+    loadNativeModule(moduleName)
+  } catch (error) {
+    failures.push(moduleName + ': ' + formatError(error))
+  }
+}
+
+if (failures.length > 0) {
+  console.error(failures.join('\\n'))
+  process.exit(1)
+}
+
+function loadNativeModule(moduleName) {
+  if (moduleName === 'better-sqlite3') {
+    const Database = projectRequire(moduleName)
+    const db = new Database(':memory:')
+    db.close()
+    return
+  }
+  if (moduleName === 'node-pty') {
+    projectRequire('node-pty')
+    const { loadNativeModule } = projectRequire('node-pty/lib/utils')
+    loadNativeModule(getNodePtyNativeModuleName())
+    return
+  }
+  projectRequire(moduleName)
+}
+
+function getNodePtyNativeModuleName() {
+  if (process.platform !== 'win32') {
+    return 'pty'
+  }
+  const match = /(\\d+)\\.(\\d+)\\.(\\d+)/g.exec(release())
+  const buildNumber = match && match.length === 4 ? Number.parseInt(match[3], 10) : 0
+  return buildNumber >= 18309 ? 'conpty' : 'pty'
+}
+
+function formatError(error) {
+  return error instanceof Error ? error.message : String(error)
+}
+`
+
+  const result = spawnSync(electronExecutable, ['-e', probeSource], {
+    cwd: projectDir,
+    env: {
+      ...process.env,
+      ELECTRON_RUN_AS_NODE: '1'
+    },
+    encoding: 'utf8',
+    stdio: ['ignore', 'pipe', 'pipe']
+  })
+
+  return {
+    ok: result.status === 0,
+    status: result.status,
+    stderr: [result.stderr, result.stdout, result.error ? formatError(result.error) : '']
+      .filter(Boolean)
+      .join('\n')
+  }
+}
+
+function isWindowsNativeLockError(error) {
+  if (process.platform !== 'win32') {
+    return false
+  }
+  const text = [error?.message, error?.stack, error?.stdout, error?.stderr]
+    .filter(Boolean)
+    .join('\n')
+  return /(?:EPERM|operation not permitted)[\s\S]*(?:unlink|\.node|conpty\.node|pty\.node)/i.test(
+    text
+  )
+}
+
+function isPostinstall() {
+  return process.env.npm_lifecycle_event === 'postinstall'
+}
+
+function formatError(error) {
+  return error instanceof Error ? error.message : String(error)
+}