Google drive won’t sync when SSL interception is enabled. The only solution is to bypass SSL Interception for these connections. This applies to both Transparent and explicit 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.
Change C:\Program Files\Google\Drive\googledrivesync.exe to C:\Program Files\Google\Drive\googledrivesync.exe" --unsafe_network
At the prompt, run googledrivesync.exe --unsafe_network
On 32bit system, the default location is at C:\Program Files\Google\Drive\
On 64bit system, the default location is at C:\Program Files (x86)\Google\Drive\
Note: This will avoid the connection failure due to SSL certificate validation by Google Drive application.