Currently, if you are trying to run a report and try to use the following settings in the screenshot (using Application/Category Names) and save it to Dropbox and if the names are too long for the paths, the report never appears in your Dropbox and there is not a notification within OpenWater that something went wrong. Adding an error could reduce escalations for this specific instance and help reps and admins alike.

Adding an error that would pop up in this use case in the top right corner of the screen that says "Error : Generated file path is too long. Try to use another download file option." would be really helpful.

This error message verbiage is taken straight from the Dev Tools console if that makes it easier :

+1!!
This would be great but I think we're fighting between a rock and hard place.
The file paths are generated dynamically based on the application and file names. If one or both push the character count (set by Windows/MacOs/Linux, enforced by Dropbox) over the limit we'll see this error.
We've considered (among other possible solutions) truncating one or both (which one? split the allocation between both?) values but again the limit will be based off more than just application title and file name ( URL generation mode and other variables) so there's no way to say "cut off at this point to avoid error".
Our dedicated solution to this is to generate files based on application/category code instead of application name while working with admins to ensure applicants are not uploading files or applications with very long names.
Worth noting when using the OpenWater Downloader or downloading reports directly this isn't an issue - it's just a reasonable restriction Dropbox has on how they handle files.
Oh but yes we should make it much easier for folks to know what went wrong, instead of some or all of the files just not showing up.
In general that could be even more helpful if there are other errors, they should be communicated outside of the console/network responses.
This has been approved and will be implemented, thank you!
You're the bomb dot com Joshua!!!!