diff --git a/circle.yml b/circle.yml
index 87341cbe..3957bc4f 100644
--- a/circle.yml
+++ b/circle.yml
@@ -23,6 +23,8 @@ jobs:
           sudo ./install.sh /usr/local
       # other deps
       - run: sudo apt -y update && sudo apt -y install python-pip python2.7 curl unzip
+      # upgrade python3.6 pip to latest
+      - run: sudo python3.6 -m pip install -U pip
       # instal pipenv
       - run: sudo python3.6 -m pip install pipenv pip-tools
       # install poetry
diff --git a/lib/inject.js b/lib/inject.js
index 1abbb531..dc30be79 100644
--- a/lib/inject.js
+++ b/lib/inject.js
@@ -37,7 +37,12 @@ function injectRequirements(requirementsPath, packagePath, options) {
             !noDeploy.has(relativeFile.split(/([-\\/]|\.py$|\.pyc$)/, 1)[0])
         )
         .map(([file, relativeFile]) =>
-          zipFile(zip, relativeFile, fse.readFileAsync(file))
+          Promise.all([file, relativeFile, fse.statAsync(file)])
+        )
+        .map(([file, relativeFile, fileStat]) =>
+          zipFile(zip, relativeFile, fse.readFileAsync(file), {
+            unixPermissions: fileStat.mode
+          })
         )
         .then(() => writeZip(zip, packagePath))
     );
diff --git a/lib/zipTree.js b/lib/zipTree.js
index ea7a9df0..d45aded0 100644
--- a/lib/zipTree.js
+++ b/lib/zipTree.js
@@ -60,14 +60,23 @@ function writeZip(zip, targetPath) {
  * @param {string} zipPath the target path in the zip.
  * @param {Promise} bufferPromise a promise providing a nodebuffer.
  * @return {Promise} a promise providing the JSZip object.
+ * @param {object} fileOpts an object with the opts to save for the file in the zip.
  */
-function zipFile(zip, zipPath, bufferPromise) {
+function zipFile(zip, zipPath, bufferPromise, fileOpts) {
   return bufferPromise
     .then(buffer =>
-      zip.file(zipPath, buffer, {
-        // necessary to get the same hash when zipping the same content
-        date: new Date(0)
-      })
+      zip.file(
+        zipPath,
+        buffer,
+        Object.assign(
+          {},
+          {
+            // necessary to get the same hash when zipping the same content
+            date: new Date(0)
+          },
+          fileOpts
+        )
+      )
     )
     .then(() => zip);
 }
diff --git a/test.js b/test.js
index 2ec71976..78f60aad 100644
--- a/test.js
+++ b/test.js
@@ -9,6 +9,7 @@ const {
   readFileSync,
   copySync,
   writeFileSync,
+  statSync,
   pathExistsSync
 } = require('fs-extra');
 const { quote } = require('shell-quote');
@@ -875,6 +876,12 @@ test(
       'foobar has retained its executable file permissions'
     );
 
+    const flaskPerm = statSync('.serverless/requirements/bin/flask').mode;
+    t.true(
+      zipfiles_with_metadata['bin/flask'].unixPermissions === flaskPerm,
+      'bin/flask has retained its executable file permissions'
+    );
+
     t.end();
   },
   { skip: process.platform === 'win32' }
@@ -1566,15 +1573,23 @@ test(
     npm(['i', path]);
     sls(['package']);
 
-    const zipfiles_hello = listZipFilesWithMetaData('.serverless/hello1.zip');
+    const zipfiles_hello1 = listZipFilesWithMetaData('.serverless/hello1.zip');
 
     t.true(
-      zipfiles_hello['module1/foobar'].unixPermissions
+      zipfiles_hello1['module1/foobar'].unixPermissions
         .toString(8)
         .slice(3, 6) === perm,
       'foobar has retained its executable file permissions'
     );
 
+    const zipfiles_hello2 = listZipFilesWithMetaData('.serverless/module2-sls-py-req-test-indiv-dev-hello2.zip');
+    const flaskPerm = statSync('.serverless/module2/requirements/bin/flask').mode;
+
+    t.true(
+      zipfiles_hello2['bin/flask'].unixPermissions === flaskPerm,
+      'bin/flask has retained its executable file permissions'
+    );
+
     t.end();
   },
   { skip: process.platform === 'win32' }
@@ -1601,6 +1616,14 @@ test(
       'foobar has retained its executable file permissions'
     );
 
+    const zipfiles_hello2 = listZipFilesWithMetaData('.serverless/module2-sls-py-req-test-indiv-dev-hello2.zip');
+    const flaskPerm = statSync('.serverless/module2/requirements/bin/flask').mode;
+
+    t.true(
+      zipfiles_hello2['bin/flask'].unixPermissions === flaskPerm,
+      'bin/flask has retained its executable file permissions'
+    );
+
     t.end();
   },
   { skip: !canUseDocker() || process.platform === 'win32' }