diff --git a/ebcli/core/fileoperations.py b/ebcli/core/fileoperations.py
index 79e319cdf..043329da6 100644
--- a/ebcli/core/fileoperations.py
+++ b/ebcli/core/fileoperations.py
@@ -18,13 +18,13 @@
 import shutil
 import stat
 import sys
-import warnings
-import yaml
 import zipfile
+import yaml
+import warnings
+from pathspec import PathSpec
 
 from cement.utils.misc import minimal_logger
 from ebcli.objects.buildconfiguration import BuildConfiguration
-from pathspec import PathSpec
 from six import StringIO
 from yaml import safe_load, safe_dump
 from yaml.parser import ParserError
@@ -431,6 +431,21 @@ def _zipdir(path, zipf, ignore_list=None):
         if '.elasticbeanstalk' in root:
             io.log_info('  -skipping: {}'.format(root))
             continue
+        for d in dirs:
+            cur_dir = os.path.join(root, d)
+            if os.path.islink(cur_dir):
+                # os.walk categorize symlinks-to-directories as dirs
+                # and we want to include symlinks in the zip
+                if cur_dir in ignore_list:
+                    io.log_info(' -skipping: {}'.format(cur_dir))
+                else:
+                    zipInfo = zipfile.ZipInfo()
+                    zipInfo.filename = os.path.join(root, d)
+
+                    # 2716663808L is the "magic code" for symlinks
+                    zipInfo.external_attr = 2716663808 if sys.version_info > (3,) else long(2716663808)
+
+                    zipf.writestr(zipInfo, os.readlink(cur_dir))
         for f in files:
             cur_file = os.path.join(root, f)
 
diff --git a/tests/unit/core/test_fileoperations.py b/tests/unit/core/test_fileoperations.py
index 1204641cd..0372a8029 100644
--- a/tests/unit/core/test_fileoperations.py
+++ b/tests/unit/core/test_fileoperations.py
@@ -717,16 +717,22 @@ def test_delete_app_file(self):
     def test_zip_up_project(self, _validate_file_for_archive_mock):
         _validate_file_for_archive_mock.side_effect = lambda f: not f.endswith('.sock')
         shutil.rmtree('home', ignore_errors=True)
-        os.mkdir('ignore-me')
-        os.mkdir('linkme')
+        os.mkdir('ignoredir')
+        os.mkdir('linkdir')
         os.mkdir('src')
         os.mkdir(os.path.join('src', 'lib'))
-        open(os.path.join('src', 'lib', 'app.py'), 'w').write('import os')
-        open(os.path.join('src', 'lib', 'app.py~'), 'w').write('import os')
-        open(os.path.join('src', 'lib', 'ignore-this-file.py'), 'w').write('import os')
-        open(os.path.join('src', 'lib', 'test.sock'), 'w').write('mock socket file')
-        open(os.path.join('ignore-me', 'text.txt'), 'w').write('import os')
-        open(os.path.join('linkme', 'foobar.txt'), 'w').write('import os linkme')
+        with open(os.path.join('src', 'lib', 'app.py'), 'w') as f:
+            f.write('import os')
+        with open(os.path.join('src', 'lib', 'app.py~'), 'w') as f:
+            f.write('import os')
+        with open(os.path.join('src', 'lib', 'ignore-this-file.py'), 'w') as f:
+            f.write('import os')
+        with open(os.path.join('src', 'lib', 'test.sock'), 'w') as f:
+            f.write('mock socket file')
+        with open(os.path.join('ignoredir', 'ignoredfile.txt'), 'w') as f:
+            f.write('import os')
+        with open(os.path.join('linkdir', 'foobar.txt'), 'w') as f:
+            f.write('import os linkdir/foobar.txt')
 
         os.symlink(
             os.path.abspath(os.path.join('src', 'lib', 'app.py')),
@@ -742,8 +748,8 @@ def test_zip_up_project(self, _validate_file_for_archive_mock):
                 target_is_directory=True
             )
             os.symlink(
-                os.path.abspath(os.path.join('linkme')),
-                os.path.abspath(os.path.join('ignore-me','linkme')),
+                os.path.abspath(os.path.join('linkdir')),
+                os.path.abspath(os.path.join('ignoredir', 'symlink-to-linkdir')),
                 target_is_directory=True
             )
         else:
@@ -751,12 +757,27 @@ def test_zip_up_project(self, _validate_file_for_archive_mock):
                 os.path.join('src', 'lib', 'api'),
                 os.path.join('src', 'lib', 'api-copy')
             )
+            os.symlink(
+                os.path.abspath(os.path.join('linkdir')),
+                os.path.abspath(os.path.join('ignoredir', 'symlink-to-linkdir'))
+            )
 
-        open(os.path.join('src', 'lib', 'api', 'api.py'), 'w').write('import unittest')
+        with open(os.path.join('src', 'lib', 'api', 'api.py'), 'w') as f:
+            f.write('import unittest')
 
         fileoperations.zip_up_project(
             'app.zip',
-            ignore_list=[os.path.join('src', 'lib', 'ignore-this-file.py'), os.path.join('ignore-me/'), os.path.join('src', 'lib', 'api-copy')]
+            ignore_list=[
+                os.path.join('src', 'lib', 'ignore-this-file.py'),
+
+                # When a directory is specified in .ebignore, the directory itself and all of its
+                # contents (files and subdirectories) are automatically added to the ignore_list recursively
+                os.path.join('ignoredir'),
+                os.path.join('ignoredir', 'ignoredfile.txt'),
+                os.path.join('ignoredir', 'symlink-to-linkdir'),
+
+                os.path.join('src', 'lib', 'api-copy')
+            ]
         )
 
         os.mkdir('tmp')
@@ -769,7 +790,7 @@ def test_zip_up_project(self, _validate_file_for_archive_mock):
         self.assertFalse(os.path.exists(os.path.join('tmp', 'src', 'lib', 'app.py~')))
         self.assertFalse(os.path.exists(os.path.join('tmp', 'src', 'lib', 'ignore-this-file.py')))
         self.assertFalse(os.path.exists(os.path.join('tmp', 'src', 'lib', 'test.sock')))
-        self.assertFalse(os.path.exists(os.path.join('tmp','ignore-me', 'link-me')))
+        self.assertFalse(os.path.exists(os.path.join('tmp', 'ignoredir', 'symlink-to-linkdir')))
 
     def test_delete_app_versions(self):
         os.mkdir(os.path.join('.elasticbeanstalk', 'app_versions'))