1) For all types of Web/Cloud file transfers like Dropbox, Securesync, Google Drive etc, Is it possible to fine type of file, its content or name?
2) Also for windows/apple update is it possible to get more details?
Answer 1) Unfortunately, we can't see the name of the files. When we look at the packets, it's merely used to get information statistics for the network monitoring i-e IPs, the application, URL if it's possible, etc. We don't go much further. Usually Payloads are encrypted so even if we try to dig deep in the packets its difficult to get that information.
Answer 2) Similarly we can not find more details about what is downloaded, but we can get the URL's if they are with in the specified ranges set under Configuration > Setup > Monitoring > Maximum URL Size. To find URL go to Monitor > Applications > Windows updates > Scroll down and click show URLs > it will open new page and there you can select the desired time period > It will give list of URL but it will not tell which URL was used for what time period and will be wrt particular host but still it might help to get some information. keep in mind that URL's are wrt host and not wrt applications, Getting URL is just getting little details of location of the downloads.