Troubleshoot Google Drive Windows App Upload Failures in SWG

Introduction

This document describes how to troubleshoot Google Drive Windows app upload failures when using Secure Web Gateway (SWG).

Prerequisites

Requirements

There are no specific requirements for this document.

Components Used

The information in this document is based on Secure Web Gateway and Umbrella Secure Internet Gateway (SIG).

The information in this document was created from the devices in a specific lab environment. All of the devices used in this document started with a cleared (default) configuration. If your network is live, ensure that you understand the potential impact of any command.

Problem

The Google Drive app does not work with any proxies that perform SSL decryption as a security measure against interception. If you enabled HTTPS Inspection in your Web Policy and deployed the Umbrella Root Certificate to all machines, you need to perform some extra steps to get the Google Drive app working. Also note, if you login to the Google Drive website, uploads can work fine, so this is only related to the app itself. If you disable HTTPS inspection the app can work, but can lower your Umbrella-related security posture (which is not recommended). 

Solution

In order to use the Google Drive app with SWG while SSL Decryption is enabled, these steps must be performed.

1. Log into your Umbrella Dashboard as a Full Admin user.

2. Navigate to Policies > Management > Web Policy.

3. You can see  HTTPS Inspection Enabled.

4. Navigate to Policies > Policy Components > Selective Decryption Lists.

5. Create a new list or edit an existing list.

6. Next to Applications Selected, select Add > Google Drive from the list and select Close.

7. Next to Domains, select Add, add these two domains, then select Close > Save.

• googleapis.com
• googledrive.com

8. Navigate back to Policies > Management > Web Policy and edit your Web Policy. 

9. Locate HTTPS Inspection and select Edit.

10. Select the Selective Decryption list you just changed, then save your changes.

Wait a few minutes for the changes to sync over. Google Drive can now work normally. 

Note: Google domains are subject to change at anytime. Please refer to this Google Support article for any updates.