diff --git a/src/azure-cli/azure/cli/command_modules/appservice/custom.py b/src/azure-cli/azure/cli/command_modules/appservice/custom.py
index fe3ec65ac8b..571c333645a 100644
--- a/src/azure-cli/azure/cli/command_modules/appservice/custom.py
+++ b/src/azure-cli/azure/cli/command_modules/appservice/custom.py
@@ -11361,7 +11361,10 @@ def _build_deploymentstatus_url(cmd, resource_group_name, webapp_name, slot, dep
 
 def _get_ondeploy_headers(params):
     if params.src_path:
-        content_type = 'application/octet-stream'
+        if params.artifact_type == 'zip':
+            content_type = 'application/zip'
+        else:
+            content_type = 'application/octet-stream'
     elif params.src_url:
         content_type = 'application/json'
     else:
diff --git a/src/azure-cli/azure/cli/command_modules/appservice/tests/latest/test_webapp_commands_thru_mock.py b/src/azure-cli/azure/cli/command_modules/appservice/tests/latest/test_webapp_commands_thru_mock.py
index cc19fbcb865..22c56edfad5 100644
--- a/src/azure-cli/azure/cli/command_modules/appservice/tests/latest/test_webapp_commands_thru_mock.py
+++ b/src/azure-cli/azure/cli/command_modules/appservice/tests/latest/test_webapp_commands_thru_mock.py
@@ -1088,6 +1088,36 @@ def _make_params(self):
         params.slot = None
         return params
 
+    @mock.patch('azure.cli.command_modules.appservice.custom._populate_cached_scm_headers')
+    @mock.patch('azure.cli.command_modules.appservice.custom.get_scm_site_headers', return_value={})
+    def test_get_ondeploy_headers_uses_zip_content_type_for_zip_artifact(
+            self, get_scm_site_headers_mock, _populate_cached_headers_mock):
+        from azure.cli.command_modules.appservice.custom import _get_ondeploy_headers
+        params = self._make_params()
+        params.src_path = '/tmp/package.zip'
+        params.artifact_type = 'zip'
+
+        _get_ondeploy_headers(params)
+
+        sent_additional_headers = get_scm_site_headers_mock.call_args.kwargs['additional_headers']
+        self.assertEqual(sent_additional_headers['Content-Type'], 'application/zip')
+        self.assertEqual(sent_additional_headers['Cache-Control'], 'no-cache')
+
+    @mock.patch('azure.cli.command_modules.appservice.custom._populate_cached_scm_headers')
+    @mock.patch('azure.cli.command_modules.appservice.custom.get_scm_site_headers', return_value={})
+    def test_get_ondeploy_headers_keeps_octet_stream_for_non_zip_artifact(
+            self, get_scm_site_headers_mock, _populate_cached_headers_mock):
+        from azure.cli.command_modules.appservice.custom import _get_ondeploy_headers
+        params = self._make_params()
+        params.src_path = '/tmp/package.war'
+        params.artifact_type = 'war'
+
+        _get_ondeploy_headers(params)
+
+        sent_additional_headers = get_scm_site_headers_mock.call_args.kwargs['additional_headers']
+        self.assertEqual(sent_additional_headers['Content-Type'], 'application/octet-stream')
+        self.assertEqual(sent_additional_headers['Cache-Control'], 'no-cache')
+
     def test_get_or_fetch_scm_url_derives_from_cached_site(self):
         from azure.cli.command_modules.appservice.custom import _get_or_fetch_scm_url
         from azure.mgmt.web.models import HostType