diff --git a/packages/aws-cdk/lib/archive.ts b/packages/aws-cdk/lib/archive.ts
index c924035bca369..9b7272ed668f2 100644
--- a/packages/aws-cdk/lib/archive.ts
+++ b/packages/aws-cdk/lib/archive.ts
@@ -1,23 +1,39 @@
 import archiver = require('archiver');
 import crypto = require('crypto');
 import fs = require('fs-extra');
+import glob = require('glob');
+import path = require('path');
 
 export function zipDirectory(directory: string, outputFile: string): Promise<void> {
   return new Promise((ok, fail) => {
     const output = fs.createWriteStream(outputFile);
     const archive = archiver('zip');
+
     // The below options are needed to support following symlinks when building zip files:
-    // -  nodir: This will prevent symlinks themselves from being copied into the zip.
+    // - nodir: This will prevent symlinks themselves from being copied into the zip.
     // - follow: This will follow symlinks and copy the files within.
     const globOptions = {
       dot: true,
       nodir: true,
       follow: true,
-      cwd: directory
+      cwd: directory,
     };
-    archive.glob('**', globOptions);
-    archive.pipe(output);
-    archive.finalize();
+    const files = glob.sync('**', globOptions); // The output here is already sorted
+
+    output.on('open', async () => {
+      archive.pipe(output);
+
+      await files.reduce(async (acc, file) => { // Append files serially to ensure file order
+        await acc;
+        const data = await fs.readFile(path.join(directory, file));
+        archive.append(data, {
+          name: file,
+          date: new Date(0), // reset dates to get the same hash for the same content
+        });
+      }, Promise.resolve());
+
+      archive.finalize();
+    });
 
     archive.on('warning', fail);
     archive.on('error', fail);
diff --git a/packages/aws-cdk/package.json b/packages/aws-cdk/package.json
index 07ef895d4d465..589eb6ca98399 100644
--- a/packages/aws-cdk/package.json
+++ b/packages/aws-cdk/package.json
@@ -60,6 +60,7 @@
     "colors": "^1.3.3",
     "decamelize": "^3.2.0",
     "fs-extra": "^8.0.1",
+    "glob": "^7.1.4",
     "json-diff": "^0.5.4",
     "minimatch": ">=3.0",
     "promptly": "^3.0.3",