My next question what about items like dropbox app, does the cert then have to sit on the machine?
AFAIK Dropbox uses a hard-coded client certificate embedded in the dropbox application and won't accept what is in the Windows and/or Firefox certificate store. Your choices are (in no specific order):
1.) permit it knowing you can't decrypt it
2.) block it because you can't decrypt it
3.) limit its use to specific people because you can't decrypt it
4.) find a different solution that is more flexible with certificates and SSL MITM
For all applications using SSL decryption, process is same. Lets say google drive uses SSL decryption, then it will work the same way gmail works. No difference.
Howe very, there are some application which do not support SSL decryption.
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