This is a problem when the proxy is deployed transparently. The only solution is to bypass SSL Interception for these connections.
The connection is breaking because of the SSL Certificate validation done by the Google Drive application. Since the certificate used for SSL Interception will be either a self-signed or a locally signed CA, Google Drive certificate validation will fail.
There is no direct way to make the Google Drive application trust the certificate used for SSL interception by the local CA/ProxySG. Google has provided an option to bypass the certificate validation by using a switch “--unsafe_network”.
Use either of the following methods to activate the switch.
- Edit the shortcut for the Google Drive and add the switch at the end:
C:\Program Files\Google\Drive\googledrivesync.exe to
C:\Program Files\Google\Drive\googledrivesync.exe" --unsafe_network
- Open a command prompt and navigate to the folder where Google Drive is installed.
At the prompt, run
Note: This is not a solution but a work around to avoid the connection failure due to SSL certificate validation at the application.