There are a few reasons why this may happen.
View the file in Incognito
CloudFiles viewer is smart. If you open the file without incognito mode, the viewer will detect that the uploader of the file (you) is trying to access and won't record the session.
Unique views vs Total views
The CloudFiles widget shows the total number of views. The Analytics modal shows the unique views. If you are refreshing the link in your incognito window, the analytics modal's unique views will not increase but the total views in widget will increase. If you close and re-open incognito window, the unqiue views will increase as well.
Navigating away from viewer
In case you see that the time is not increasing while you have the file open in another window in the background, it is because the CloudFiles' viewer has detected that you have navigated away from the document and so are not reading it. Keep the document open for some time. Read it. The time will increase.
Sometimes the analytics modal or the widget may not auto-refresh for a plethora of reasons related to app, HubSpot, the browser or even your computer screen. The best solution is to manually refresh the browser and check the views/time again.
Finally, if nothing works, starting from a clean slate almost always does. You can simply delete the existing file and re-upload a new one. This solution is not suitable for files which have shared links. Deleting the file will render the current link inaccessible.
In case the problem persists, please raise a ticket or write to us detailing the specific issue. We will get back to you as soon as possible.