diff --git a/lib/hash.js b/lib/hash.js
index 8d7d3fd..fea3c53 100644
--- a/lib/hash.js
+++ b/lib/hash.js
@@ -9,11 +9,18 @@ import { readFile } from 'fs-promise';
  */
 
 export default async function hashes (files) {
-  const entries = await Promise.all(files.map(async (name) => {
+  const map = new Map();
+  await Promise.all(files.map(async (name) => {
     const data = await readFile(name);
-    return [hash(data), { name, data }];
+    const h = hash(data);
+    const entry = map.get(h);
+    if (entry) {
+      entry.names.push(name);
+    } else {
+      map.set(hash(data), { names: [name], data });
+    }
   }));
-  return new Map(entries);
+  return map;
 }
 
 /**
diff --git a/lib/index.js b/lib/index.js
index c85588b..8906500 100644
--- a/lib/index.js
+++ b/lib/index.js
@@ -82,13 +82,15 @@ export default class Now extends EventEmitter {
           forceSync,
           name: pkg.name || basename(path),
           description: pkg.description,
-          files: Array.from(this._files).map(([sha, { data, name }]) => {
-            return {
-              sha,
-              size: data.length,
-              file: toRelative(name, this._path)
-            };
-          })
+          files: [].concat.apply([], Array.from(this._files).map(([sha, { data, names }]) => {
+            return names.map((name) => {
+              return {
+                sha,
+                size: data.length,
+                file: toRelative(name, this._path)
+              };
+            });
+          }))
         }
       });
       if (this._debug) console.timeEnd('> [debug] /create');
@@ -127,9 +129,9 @@ export default class Now extends EventEmitter {
     const uploadChunk = () => {
       Promise.all(parts.shift().map((sha) => retry(async (bail) => {
         const file = this._files.get(sha);
-        const { data, name } = file;
+        const { data, names } = file;
 
-        if (this._debug) console.time(`> [debug] /sync ${name}`);
+        if (this._debug) console.time(`> [debug] /sync ${names.join(' ')}`);
 
         const stream = resumer().queue(data).end();
         const res = await this._fetch('/sync', {
@@ -139,12 +141,12 @@ export default class Now extends EventEmitter {
             'Content-Length': data.length,
             'x-now-deployment-id': this._id,
             'x-now-sha': sha,
-            'x-now-file': toRelative(name, this._path),
+            'x-now-file': names.map((name) => toRelative(name, this._path)).join(','),
             'x-now-size': data.length
           },
           body: stream
         });
-        if (this._debug) console.timeEnd(`> [debug] /sync ${name}`);
+        if (this._debug) console.timeEnd(`> [debug] /sync ${names.join(' ')}`);
 
         // no retry on 4xx
         if (200 !== res.status && (400 <= res.status || 500 > res.status)) {