diff --git a/src/application/AppBundleExecutable.test.ts b/src/application/AppBundleExecutable.test.ts
index 942a001122..d32e6bdd2b 100644
--- a/src/application/AppBundleExecutable.test.ts
+++ b/src/application/AppBundleExecutable.test.ts
@@ -32,3 +32,46 @@ describe("app bundle Info.plist magic", () => {
     }
   });
 });
+
+describe("app bundle program directory containment", () => {
+  it("rejects an escaping programs directory before resolving its child", async () => {
+    const root = await mkdtemp(join(tmpdir(), "rea-app-programs-"));
+    try {
+      const bundle = join(root, "Fixture.app");
+      const programs = join(bundle, "Contents", "MacOS");
+      const executable = join(programs, "Missing");
+      const canonicalBundle = join(root, "Canonical.app");
+      const outsidePrograms = join(root, "outside");
+      const plist =
+        "<plist><dict><key>CFBundleExecutable</key><string>Missing</string></dict></plist>";
+      await mkdir(join(bundle, "Contents"), { recursive: true });
+      await writeFile(join(bundle, "Contents", "Info.plist"), plist);
+      let childResolved = false;
+
+      const result = await resolveAppBundleExecutable(bundle, {
+        readFile: async () => Buffer.from(plist),
+        realpath: async (path) => {
+          if (path === bundle) return canonicalBundle;
+          if (path === programs) return outsidePrograms;
+          if (path === executable) {
+            childResolved = true;
+            throw Object.assign(new Error("missing executable"), {
+              code: "ENOENT",
+            });
+          }
+          return path;
+        },
+      });
+
+      expect(result).toMatchObject({
+        ok: false,
+        error: {
+          reason: "app program directory leaves Contents/MacOS",
+        },
+      });
+      expect(childResolved).toBe(false);
+    } finally {
+      await rm(root, { recursive: true, force: true });
+    }
+  });
+});
diff --git a/src/application/AppBundleExecutable.ts b/src/application/AppBundleExecutable.ts
index 7ab79a3cf4..eff93d5dae 100644
--- a/src/application/AppBundleExecutable.ts
+++ b/src/application/AppBundleExecutable.ts
@@ -219,11 +219,24 @@ const resolveLayoutExecutable = async (
     );
   const programs = join(bundle, ...layout.programs);
   const executable = join(programs, name);
+  let canonicalBundle: string;
   try {
-    const [canonicalPrograms, canonicalExecutable] = await Promise.all([
-      fileSystem.realpath(programs),
-      fileSystem.realpath(executable),
-    ]);
+    canonicalBundle = await fileSystem.realpath(bundle);
+  } catch (cause: unknown) {
+    return err(
+      new BinaryTargetError(bundle, errorReason(cause, bundle), { cause }),
+    );
+  }
+  try {
+    const canonicalPrograms = await fileSystem.realpath(programs);
+    if (!isPathWithinRoot(canonicalBundle, canonicalPrograms))
+      return err(
+        new BinaryTargetError(
+          bundle,
+          `app program directory leaves ${layout.programsLabel}`,
+        ),
+      );
+    const canonicalExecutable = await fileSystem.realpath(executable);
     if (!isPathWithinRoot(canonicalPrograms, canonicalExecutable))
       return err(
         new BinaryTargetError(
diff --git a/tests/boundary/filesystem/binaryTarget.test.ts b/tests/boundary/filesystem/binaryTarget.test.ts
index ad3d663949..3a8263c5f1 100644
--- a/tests/boundary/filesystem/binaryTarget.test.ts
+++ b/tests/boundary/filesystem/binaryTarget.test.ts
@@ -429,7 +429,9 @@ describe("binary target I/O: filesystem and app bundle target resolution", () =>
       ).ok,
     ).toBe(false);
   });
+});
 
+describe("app bundle canonical containment", () => {
   it.skipIf(process.platform === "win32")(
     "rejects an app program symlink that leaves the bundle",
     async () => {
@@ -455,6 +457,68 @@ describe("binary target I/O: filesystem and app bundle target resolution", () =>
       ).toBe(false);
     },
   );
+
+  it.skipIf(process.platform === "win32")(
+    "rejects a Contents/MacOS directory symlink that leaves the bundle",
+    async () => {
+      const directory = await createTestTempDirectory("rea-target-");
+      const app = join(directory, "Escaping.app");
+      const contents = join(app, "Contents");
+      const programs = join(contents, "MacOS");
+      const outside = join(directory, "outside");
+      await mkdir(contents, { recursive: true });
+      await mkdir(outside);
+      await writeFile(
+        join(contents, "Info.plist"),
+        "<plist><dict><key>CFBundleExecutable</key><string>Escaping</string></dict></plist>",
+      );
+      await writeFile(
+        join(outside, "Escaping"),
+        thinMach(0xfeedfacf, 0x0100000c),
+      );
+      await symlink(outside, programs, "dir");
+
+      const result = await parseBinaryTarget(app, {
+        cwd: directory,
+        hostArchitecture: "arm64",
+      });
+      expect(result).toMatchObject({
+        ok: false,
+        error: {
+          path: app,
+          reason: "app program directory leaves Contents/MacOS",
+        },
+      });
+    },
+  );
+
+  it.skipIf(process.platform === "win32")(
+    "allows bundle and program directory aliases within the canonical bundle",
+    async () => {
+      const directory = await createTestTempDirectory("rea-target-");
+      const app = join(directory, "Canonical.app");
+      const alias = join(directory, "Alias.app");
+      const contents = join(app, "Contents");
+      const programs = join(contents, "Programs");
+      const executable = join(programs, "Example");
+      await mkdir(programs, { recursive: true });
+      await writeFile(executable, thinMach(0xfeedfacf, 0x0100000c));
+      await writeFile(
+        join(contents, "Info.plist"),
+        "<plist><dict><key>CFBundleExecutable</key><string>Example</string></dict></plist>",
+      );
+      await symlink(programs, join(contents, "MacOS"), "dir");
+      await symlink(app, alias, "dir");
+      const result = await parseBinaryTarget(alias, {
+        cwd: directory,
+        hostArchitecture: "arm64",
+      });
+      expect(result).toMatchObject({
+        ok: true,
+        value: { path: await realpath(executable), format: "mach-o" },
+      });
+    },
+  );
 });
 
 describe("binary target I/O: explicit kinds and executable headers", () => {