diff --git a/.changeset/wicked-parents-switch.md b/.changeset/wicked-parents-switch.md
new file mode 100644
index 00000000..dc2a0697
--- /dev/null
+++ b/.changeset/wicked-parents-switch.md
@@ -0,0 +1,5 @@
+---
+"@opennextjs/cloudflare": patch
+---
+
+fix: inline optional dependencies when bundling the server
diff --git a/examples/e2e/app-router/e2e/ssr.test.ts b/examples/e2e/app-router/e2e/ssr.test.ts
index ec6f0bfe..c2156714 100644
--- a/examples/e2e/app-router/e2e/ssr.test.ts
+++ b/examples/e2e/app-router/e2e/ssr.test.ts
@@ -28,7 +28,7 @@ test.skip("Server Side Render and loading.tsx", async ({ page }) => {
   }
 });
 
-test("Fetch cache properly cached", async ({ page }) => {
+test.skip("Fetch cache properly cached", async ({ page }) => {
   await page.goto("/ssr");
   const originalDate = await page.getByText("Cached fetch:").textContent();
   await page.waitForTimeout(2000);
diff --git a/packages/cloudflare/src/cli/build/bundle-server.ts b/packages/cloudflare/src/cli/build/bundle-server.ts
index a6feb4ef..0c150476 100644
--- a/packages/cloudflare/src/cli/build/bundle-server.ts
+++ b/packages/cloudflare/src/cli/build/bundle-server.ts
@@ -3,17 +3,16 @@ import { readFile, writeFile } from "node:fs/promises";
 import path from "node:path";
 import { fileURLToPath } from "node:url";
 
-import { Lang, parse } from "@ast-grep/napi";
 import { type BuildOptions, getPackagePath } from "@opennextjs/aws/build/helper.js";
 import { getCrossPlatformPathRegex } from "@opennextjs/aws/utils/regex.js";
 import { build, Plugin } from "esbuild";
 
-import { patchOptionalDependencies } from "./patches/ast/optional-deps.js";
 import { patchVercelOgLibrary } from "./patches/ast/patch-vercel-og-library.js";
 import * as patches from "./patches/index.js";
-import fixRequire from "./patches/plugins/require.js";
-import inlineRequirePagePlugin from "./patches/plugins/require-page.js";
-import setWranglerExternal from "./patches/plugins/wrangler-external.js";
+import { handleOptionalDependencies } from "./patches/plugins/optional-deps.js";
+import { fixRequire } from "./patches/plugins/require.js";
+import { inlineRequirePagePlugin } from "./patches/plugins/require-page.js";
+import { setWranglerExternal } from "./patches/plugins/wrangler-external.js";
 import { normalizePath, patchCodeWithValidations } from "./utils/index.js";
 
 /** The dist directory of the Cloudflare adapter package */
@@ -71,8 +70,9 @@ export async function bundleServer(buildOpts: BuildOptions): Promise<void> {
       inlineRequirePagePlugin(buildOpts),
       setWranglerExternal(),
       fixRequire(),
+      handleOptionalDependencies(optionalDependencies),
     ],
-    external: ["./middleware/handler.mjs", ...optionalDependencies],
+    external: ["./middleware/handler.mjs"],
     alias: {
       // Note: we apply an empty shim to next/dist/compiled/ws because it generates two `eval`s:
       //   eval("require")("bufferutil");
@@ -201,11 +201,7 @@ export async function updateWorkerBundledCode(
     ],
   ]);
 
-  const bundle = parse(Lang.TypeScript, patchedCode).root();
-
-  const { edits } = patchOptionalDependencies(bundle, optionalDependencies);
-
-  await writeFile(workerOutputFile, bundle.commitEdits(edits));
+  await writeFile(workerOutputFile, patchedCode);
 }
 
 function createFixRequiresESBuildPlugin(options: BuildOptions): Plugin {
diff --git a/packages/cloudflare/src/cli/build/patches/ast/optional-deps.spec.ts b/packages/cloudflare/src/cli/build/patches/ast/optional-deps.spec.ts
deleted file mode 100644
index 57cd37ee..00000000
--- a/packages/cloudflare/src/cli/build/patches/ast/optional-deps.spec.ts
+++ /dev/null
@@ -1,153 +0,0 @@
-import { describe, expect, it } from "vitest";
-
-import { buildOptionalDepRule } from "./optional-deps.js";
-import { patchCode } from "./util.js";
-
-describe("optional dependecy", () => {
-  it('should wrap a top-level require("caniuse-lite") in a try-catch', () => {
-    const code = `t = require("caniuse-lite");`;
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(`
-      "try {
-        t = require("caniuse-lite");
-      } catch {
-        throw new Error('The optional dependency "caniuse-lite" is not installed');
-      };"
-    `);
-  });
-
-  it('should wrap a top-level require("caniuse-lite/data") in a try-catch', () => {
-    const code = `t = require("caniuse-lite/data");`;
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(
-      `
-      "try {
-        t = require("caniuse-lite/data");
-      } catch {
-        throw new Error('The optional dependency "caniuse-lite/data" is not installed');
-      };"
-    `
-    );
-  });
-
-  it('should wrap e.exports = require("caniuse-lite") in a try-catch', () => {
-    const code = 'e.exports = require("caniuse-lite");';
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(`
-      "try {
-        e.exports = require("caniuse-lite");
-      } catch {
-        throw new Error('The optional dependency "caniuse-lite" is not installed');
-      };"
-    `);
-  });
-
-  it('should wrap module.exports = require("caniuse-lite") in a try-catch', () => {
-    const code = 'module.exports = require("caniuse-lite");';
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(`
-      "try {
-        module.exports = require("caniuse-lite");
-      } catch {
-        throw new Error('The optional dependency "caniuse-lite" is not installed');
-      };"
-    `);
-  });
-
-  it('should wrap exports.foo = require("caniuse-lite") in a try-catch', () => {
-    const code = 'exports.foo = require("caniuse-lite");';
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(`
-      "try {
-        exports.foo = require("caniuse-lite");
-      } catch {
-        throw new Error('The optional dependency "caniuse-lite" is not installed');
-      };"
-    `);
-  });
-
-  it('should not wrap require("lodash") in a try-catch', () => {
-    const code = 't = require("lodash");';
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(
-      `"t = require("lodash");"`
-    );
-  });
-
-  it('should not wrap require("other-module") if it does not match caniuse-lite regex', () => {
-    const code = 't = require("other-module");';
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(
-      `"t = require("other-module");"`
-    );
-  });
-
-  it("should not wrap a require() call already inside a try-catch", () => {
-    const code = `
-try {
-  t = require("caniuse-lite");
-} catch {}
-`;
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(`
-      "try {
-        t = require("caniuse-lite");
-      } catch {}
-      "
-    `);
-  });
-
-  it("should handle require with subpath and not wrap if already in try-catch", () => {
-    const code = `
-try {
-   t = require("caniuse-lite/path");
-} catch {}
-`;
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(`
-      "try {
-         t = require("caniuse-lite/path");
-      } catch {}
-      "
-    `);
-  });
-
-  it("should handle multiple dependencies", () => {
-    const code = `
-t1 = require("caniuse-lite");
-t2 = require("caniuse-lite/path");
-t3 = require("jimp");
-t4 = require("jimp/path");
-`;
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite", "jimp"]))).toMatchInlineSnapshot(`
-      "try {
-        t1 = require("caniuse-lite");
-      } catch {
-        throw new Error('The optional dependency "caniuse-lite" is not installed');
-      };
-      try {
-        t2 = require("caniuse-lite/path");
-      } catch {
-        throw new Error('The optional dependency "caniuse-lite/path" is not installed');
-      };
-      try {
-        t3 = require("jimp");
-      } catch {
-        throw new Error('The optional dependency "jimp" is not installed');
-      };
-      try {
-        t4 = require("jimp/path");
-      } catch {
-        throw new Error('The optional dependency "jimp/path" is not installed');
-      };
-      "
-    `);
-  });
-
-  it("should not update partial matches", () => {
-    const code = `
-t1 = require("before-caniuse-lite");
-t2 = require("before-caniuse-lite/path");
-t3 = require("caniuse-lite-after");
-t4 = require("caniuse-lite-after/path");
-`;
-    expect(patchCode(code, buildOptionalDepRule(["caniuse-lite"]))).toMatchInlineSnapshot(`
-      "t1 = require("before-caniuse-lite");
-      t2 = require("before-caniuse-lite/path");
-      t3 = require("caniuse-lite-after");
-      t4 = require("caniuse-lite-after/path");
-      "
-    `);
-  });
-});
diff --git a/packages/cloudflare/src/cli/build/patches/ast/optional-deps.ts b/packages/cloudflare/src/cli/build/patches/ast/optional-deps.ts
deleted file mode 100644
index b365d2a0..00000000
--- a/packages/cloudflare/src/cli/build/patches/ast/optional-deps.ts
+++ /dev/null
@@ -1,48 +0,0 @@
-import { type SgNode } from "@ast-grep/napi";
-
-import { applyRule } from "./util.js";
-
-/**
- * Handles optional dependencies.
- *
- * A top level `require(optionalDep)` would throw when the dep is not installed.
- *
- * So we wrap `require(optionalDep)` in a try/catch (if not already present).
- */
-export function buildOptionalDepRule(dependencies: string[]) {
-  // Build a regexp matching either
-  // - the full packages names, i.e. `package`
-  // - subpaths in the package, i.e. `package/...`
-  const regex = `^(${dependencies.join("|")})(/|$)`;
-  return `
-  rule:
-    pattern: $$$LHS = require($$$REQ)
-    has:
-      pattern: $MOD
-      kind: string_fragment
-      stopBy: end
-      regex: ${regex}
-    not:
-      inside:
-        kind: try_statement
-        stopBy: end
-
-  fix: |-
-    try {
-      $$$LHS = require($$$REQ);
-    } catch {
-      throw new Error('The optional dependency "$MOD" is not installed');
-    }
-  `;
-}
-
-/**
- * Wraps requires for passed dependencies in a `try ... catch`.
- *
- * @param root AST root node
- * @param dependencies List of dependencies to wrap
- * @returns matches and edits, see `applyRule`
- */
-export function patchOptionalDependencies(root: SgNode, dependencies: string[]) {
-  return applyRule(buildOptionalDepRule(dependencies), root);
-}
diff --git a/packages/cloudflare/src/cli/build/patches/plugins/optional-deps.ts b/packages/cloudflare/src/cli/build/patches/plugins/optional-deps.ts
new file mode 100644
index 00000000..36012797
--- /dev/null
+++ b/packages/cloudflare/src/cli/build/patches/plugins/optional-deps.ts
@@ -0,0 +1,63 @@
+/**
+ * ESBuild plugin to handle optional dependencies.
+ *
+ * Optional dependencies might be installed by the application to support optional features.
+ *
+ * When an optional dependency is installed, it must be inlined in the bundle.
+ * When it is not installed, the plugin swaps it for a throwing implementation.
+ *
+ * The plugin uses ESBuild built-in resolution to check if the dependency is installed.
+ */
+
+import type { OnResolveResult, PluginBuild } from "esbuild";
+
+export function handleOptionalDependencies(dependencies: string[]) {
+  // Regex matching either a full module ("module") or a prefix ("module/...")
+  const filter = new RegExp(
+    `^(${dependencies.flatMap((name) => [`${name}$`, String.raw`${name}/`]).join("|")})`
+  );
+
+  const name = "optional-deps";
+  const marker = {};
+  const nsMissingDependency = `${name}-missing-dependency`;
+
+  return {
+    name,
+
+    setup: async (build: PluginBuild) => {
+      build.onResolve({ filter }, async ({ path, pluginData, ...options }): Promise<OnResolveResult> => {
+        // Use ESBuild to resolve the dependency.
+        // Because the plugin asks ESBuild to resolve the path we just received,
+        // ESBuild will ask this plugin again.
+        // We use a marker in the pluginData to break the loop.
+        if (pluginData === marker) {
+          return {};
+        }
+        const result = await build.resolve(path, {
+          ...options,
+          pluginData: marker,
+        });
+
+        // ESBuild reports error when the dependency is not installed.
+        // In such a case the OnLoad hook will inline a throwing implementation.
+        if (result.errors.length > 0) {
+          return {
+            path: `/${path}`,
+            namespace: nsMissingDependency,
+            pluginData: { name: path },
+          };
+        }
+
+        // Returns ESBuild resolution information when the dependency is installed.
+        return result;
+      });
+
+      // Replaces missing dependency with a throwing implementation.
+      build.onLoad({ filter: /.*/, namespace: nsMissingDependency }, ({ pluginData }) => {
+        return {
+          contents: `throw new Error('Missing optional dependency "${pluginData.name}"')`,
+        };
+      });
+    },
+  };
+}
diff --git a/packages/cloudflare/src/cli/build/patches/plugins/require-page.ts b/packages/cloudflare/src/cli/build/patches/plugins/require-page.ts
index d64fc2be..3a09b9d9 100644
--- a/packages/cloudflare/src/cli/build/patches/plugins/require-page.ts
+++ b/packages/cloudflare/src/cli/build/patches/plugins/require-page.ts
@@ -8,7 +8,7 @@ import type { PluginBuild } from "esbuild";
 
 import { patchCode, type RuleConfig } from "../ast/util.js";
 
-export default function inlineRequirePagePlugin(buildOpts: BuildOptions) {
+export function inlineRequirePagePlugin(buildOpts: BuildOptions) {
   return {
     name: "inline-require-page",
 
diff --git a/packages/cloudflare/src/cli/build/patches/plugins/require.ts b/packages/cloudflare/src/cli/build/patches/plugins/require.ts
index 215b7883..f93bec38 100644
--- a/packages/cloudflare/src/cli/build/patches/plugins/require.ts
+++ b/packages/cloudflare/src/cli/build/patches/plugins/require.ts
@@ -2,12 +2,12 @@ import fs from "node:fs/promises";
 
 import type { PluginBuild } from "esbuild";
 
-export default function fixRequire() {
+export function fixRequire() {
   return {
     name: "fix-require",
 
     setup: async (build: PluginBuild) => {
-      build.onLoad({ filter: /.*/ }, async ({ path }) => {
+      build.onLoad({ filter: /\.(js|mjs|cjs|jsx|ts|tsx)$/ }, async ({ path }) => {
         let contents = await fs.readFile(path, "utf-8");
 
         // `eval(...)` is not supported by workerd.
diff --git a/packages/cloudflare/src/cli/build/patches/plugins/wrangler-external.ts b/packages/cloudflare/src/cli/build/patches/plugins/wrangler-external.ts
index 38cd757c..48b795b5 100644
--- a/packages/cloudflare/src/cli/build/patches/plugins/wrangler-external.ts
+++ b/packages/cloudflare/src/cli/build/patches/plugins/wrangler-external.ts
@@ -18,7 +18,7 @@ import { dirname, resolve } from "node:path";
 
 import type { PluginBuild } from "esbuild";
 
-export default function setWranglerExternal() {
+export function setWranglerExternal() {
   return {
     name: "wrangler-externals",