Yup, that would be expected for something like the Google Drive application or Dropbox as two examples. This is due to certificate pinning on the application itself, so when the certificate doesn't match what's expected the client just drops all traffic. You'll want to create a decryption exclusion to actually make the application itself work or force users to migrate to using the actual web interface. Depending on the severity of the files you are working with and your risk level acceptance, you could do either.
The exceptions that you'll want to make :
Google Drive for your PC/Mac
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