diff --git a/config/scripts/build-orcad.mjs b/config/scripts/build-orcad.mjs
index d548e5c65d1..351f71b51d0 100644
--- a/config/scripts/build-orcad.mjs
+++ b/config/scripts/build-orcad.mjs
@@ -9,6 +9,7 @@ import {
   externalNativeAddons,
   ORCAD_EXTERNAL_MODULES,
   ORCAD_CHILD_ENTRY_POINTS,
+  ORCAD_COMMONJS_MODULE_OPTIONS,
   orcadChildOutputFilename
 } from './orcad-entry-build.mjs'
 import { createRequire } from 'node:module'
@@ -52,6 +53,8 @@ import { computeOrcadFullVersion } from './orcad-artifact-version.mjs'
 import { NODE_RUNTIME_ASSETS, NODE_RUNTIME_PIN } from '../../src/shared/node-runtime-pin.ts'
 import { findSlotProblems, readManifest } from './orcad-prebuild-slot-contents.mjs'
 import { orcadAgentBrowserNativeName } from '../../src/shared/orcad-agent-browser-name.ts'
+import { runProcessSync } from '@orca/process-host'
+import { describeProcessFailure } from './process-failure-message.mjs'
 
 const ROOT = join(import.meta.dirname, '..', '..')
 const OUT_DIR = process.env.ORCAD_OUT_DIR
@@ -99,6 +102,7 @@ async function stageParcelWatcher(target) {
   const wrapperSource = requireFromWatcher.resolve('@parcel/watcher/wrapper.js')
   mkdirSync(WATCHER_MODULE_DIR, { recursive: true })
   await build({
+    ...ORCAD_COMMONJS_MODULE_OPTIONS,
     stdin: {
       contents:
         `const {createWrapper}=require(${JSON.stringify(wrapperSource)});` +
@@ -197,6 +201,7 @@ cpSync(join(ROOT, 'resources', 'native-chat-visuals'), join(OUT_DIR, 'native-cha
  *  their runtime resolvers look for them. */
 function buildForkedChild(entryPoint, outfile) {
   return build({
+    ...ORCAD_COMMONJS_MODULE_OPTIONS,
     entryPoints: [entryPoint],
     bundle: true,
     platform: 'node',
@@ -209,6 +214,7 @@ function buildForkedChild(entryPoint, outfile) {
     minify: true,
     sourcemap: false,
     define: {
+      ...ORCAD_COMMONJS_MODULE_OPTIONS.define,
       'process.env.NODE_ENV': '"production"'
     },
     logLevel: 'error'
@@ -312,6 +318,17 @@ if (graphErrors.length > 0) {
     )
     process.exitCode = 1
   }
+  const providerSmoke = runProcessSync({
+    program: process.execPath,
+    args: [SERVER_OUT_FILE, '--orcad-structured-provider-load-check'],
+    timeoutMs: 60_000
+  })
+  if (providerSmoke.code !== 0 || providerSmoke.timedOut || providerSmoke.outputTruncated) {
+    console.error(
+      `[build-orcad] the packaged structured provider failed to load.\n${describeProcessFailure(providerSmoke)}`
+    )
+    process.exitCode = 1
+  }
   // Why require + parseArgs and not a real daemon: requiring the bundle evaluates every
   // top-level import, and calling its exported argv parser proves the entry's own code is
   // there rather than a graph that merely resolved. Booting one would need a socket, a
diff --git a/config/scripts/orcad-entry-build.mjs b/config/scripts/orcad-entry-build.mjs
index 1f0de9a11b2..7b636937b3e 100644
--- a/config/scripts/orcad-entry-build.mjs
+++ b/config/scripts/orcad-entry-build.mjs
@@ -25,6 +25,15 @@ export function orcadChildOutputFilename(entryPoint) {
 
 export const ORCAD_EXTERNAL_MODULES = ['electron', 'node-pty', '@parcel/watcher', 'fsevents']
 
+// Bundled ESM resolves from the deployed bundle, like CommonJS __filename.
+export const ORCAD_COMMONJS_MODULE_OPTIONS = {
+  banner: {
+    js: 'var __orcadModuleUrl = require("node:url").pathToFileURL(__filename).href;'
+  },
+  define: { 'import.meta.url': '__orcadModuleUrl' },
+  logOverride: { 'empty-import-meta': 'error' }
+}
+
 // Native binaries are staged separately from every JavaScript entry.
 export const externalNativeAddons = {
   name: 'external-native-addons',
@@ -45,6 +54,7 @@ const jsoncParserEsm = {
 
 export function buildOrcadEntry(outfile) {
   return build({
+    ...ORCAD_COMMONJS_MODULE_OPTIONS,
     entryPoints: [join(root, ORCAD_ENTRY_POINT)],
     bundle: true,
     platform: 'node',
@@ -56,7 +66,10 @@ export function buildOrcadEntry(outfile) {
     metafile: true,
     minify: true,
     sourcemap: false,
-    define: { 'process.env.NODE_ENV': '"production"' },
+    define: {
+      ...ORCAD_COMMONJS_MODULE_OPTIONS.define,
+      'process.env.NODE_ENV': '"production"'
+    },
     logLevel: 'error'
   })
 }
@@ -81,6 +94,7 @@ export function buildOrcadLauncher(outfile) {
     .update(readFileSync(join(dirname(outfile), ORCAD_SERVER_ENTRY_FILENAME)))
     .digest('hex')
   return build({
+    ...ORCAD_COMMONJS_MODULE_OPTIONS,
     entryPoints: [join(root, ORCAD_LAUNCHER_ENTRY_POINT)],
     bundle: true,
     platform: 'node',
@@ -90,7 +104,10 @@ export function buildOrcadLauncher(outfile) {
     metafile: true,
     minify: true,
     sourcemap: false,
-    define: { ORCAD_SERVER_SHA256: JSON.stringify(serverSha256) },
+    define: {
+      ...ORCAD_COMMONJS_MODULE_OPTIONS.define,
+      ORCAD_SERVER_SHA256: JSON.stringify(serverSha256)
+    },
     logLevel: 'error'
   })
 }
diff --git a/config/scripts/orcad-entry-build.test.mjs b/config/scripts/orcad-entry-build.test.mjs
new file mode 100644
index 00000000000..b367aba66ad
--- /dev/null
+++ b/config/scripts/orcad-entry-build.test.mjs
@@ -0,0 +1,79 @@
+import { build } from 'esbuild'
+import { mkdirSync, mkdtempSync, renameSync, rmSync, writeFileSync } from 'node:fs'
+import { tmpdir } from 'node:os'
+import { join } from 'node:path'
+import { afterAll, beforeAll, expect, it } from 'vitest'
+import { buildOrcadEntry, ORCAD_COMMONJS_MODULE_OPTIONS } from './orcad-entry-build.mjs'
+import { runProcessSync } from '@orca/process-host'
+
+const directory = mkdtempSync(join(tmpdir(), 'orca-structured-provider-build-'))
+const bundle = join(directory, 'orcad-server.js')
+
+beforeAll(async () => {
+  await buildOrcadEntry(bundle)
+}, 60_000)
+
+afterAll(() => {
+  rmSync(directory, { recursive: true, force: true })
+})
+
+it('loads the structured Claude SDK through the packaged server under plain Node', () => {
+  const loaded = runProcessSync({
+    program: process.execPath,
+    args: [bundle, '--orcad-structured-provider-load-check'],
+    cwd: directory,
+    env: { ORCA_BACKGROUND_LAUNCH: '1' },
+    timeoutMs: 30_000
+  })
+  expect(loaded.code, loaded.stderr.slice(-2_000)).toBe(0)
+}, 40_000)
+
+it('resolves bundle-relative requires after deployment to a path with URL-special characters', async () => {
+  const buildDirectory = join(directory, 'build')
+  mkdirSync(buildDirectory)
+  const outfile = join(buildDirectory, 'entry.cjs')
+  await build({
+    ...ORCAD_COMMONJS_MODULE_OPTIONS,
+    stdin: {
+      contents: `import { createRequire } from 'node:module';
+        console.log(createRequire(import.meta.url)('./asset.cjs'));`,
+      resolveDir: directory
+    },
+    bundle: true,
+    platform: 'node',
+    target: 'node18',
+    format: 'cjs',
+    outfile,
+    minify: true,
+    logLevel: 'error'
+  })
+  writeFileSync(join(buildDirectory, 'asset.cjs'), 'module.exports = "deployed asset"')
+  const deployedDirectory = join(directory, 'deployed # 100%')
+  renameSync(buildDirectory, deployedDirectory)
+  const loaded = runProcessSync({
+    program: process.execPath,
+    args: [join(deployedDirectory, 'entry.cjs')],
+    cwd: directory,
+    env: { ORCA_BACKGROUND_LAUNCH: '1' },
+    timeoutMs: 30_000
+  })
+  expect(loaded.code, loaded.stderr).toBe(0)
+  expect(loaded.stdout.trim()).toBe('deployed asset')
+})
+
+it.each(['import.meta', 'import.meta.dirname', 'import.meta.filename', 'import.meta.resolve'])(
+  'rejects unsupported %s instead of silently replacing it with an empty object',
+  async (expression) => {
+    await expect(
+      build({
+        ...ORCAD_COMMONJS_MODULE_OPTIONS,
+        stdin: { contents: `console.log(${expression})`, resolveDir: directory },
+        bundle: true,
+        platform: 'node',
+        format: 'cjs',
+        write: false,
+        logLevel: 'silent'
+      })
+    ).rejects.toThrow('"import.meta" is not available')
+  }
+)
diff --git a/src/main/orcad/main.ts b/src/main/orcad/main.ts
index 30e21462a8f..ca28cea4174 100644
--- a/src/main/orcad/main.ts
+++ b/src/main/orcad/main.ts
@@ -42,7 +42,12 @@ function failStartup(error: unknown): void {
 }
 
 // One-shot launch and stop commands must skip server startup and preflights.
-if (process.argv[2] === WINDOWS_BREAKAWAY_LAUNCH_FLAG) {
+if (process.argv[2] === '--orcad-structured-provider-load-check') {
+  void import('./orcad-structured-provider-smoke')
+    .then(({ smokeLoadOrcadStructuredProviders }) => smokeLoadOrcadStructuredProviders())
+    .then(() => process.exit(0))
+    .catch(failStartup)
+} else if (process.argv[2] === WINDOWS_BREAKAWAY_LAUNCH_FLAG) {
   runWindowsBreakawayLaunchIfRequested(ORCAD_WINDOWS_BREAKAWAY_CONTRACT, process.argv)
 } else if (
   process.argv[2] === ORCAD_COMPLETE_MANAGED_STOP_FLAG ||
diff --git a/src/main/orcad/orcad-structured-provider-smoke.ts b/src/main/orcad/orcad-structured-provider-smoke.ts
new file mode 100644
index 00000000000..7e64c62f38a
--- /dev/null
+++ b/src/main/orcad/orcad-structured-provider-smoke.ts
@@ -0,0 +1,22 @@
+import { openClaudeStreamJsonConnection } from '../claude/claude-stream-json-connection'
+
+export async function smokeLoadOrcadStructuredProviders(): Promise<void> {
+  const loaded = new Error('structured provider module loaded')
+  try {
+    await openClaudeStreamJsonConnection(
+      { pathToClaudeCodeExecutable: 'unused', cwd: process.cwd(), options: {} },
+      {},
+      undefined,
+      () => {
+        // The production connection loads the SDK before calling the query implementation.
+        throw loaded
+      }
+    )
+  } catch (error) {
+    if (error === loaded) {
+      return
+    }
+    throw error
+  }
+  throw new Error('structured provider load check did not reach the SDK boundary')
+}