Expectation of multi-select and opening in an app is not clear

[lynwilhelm]

It is not very clear that you can't open multiple files in an application.

Is there ever a case where we will support this? (i.e. a segmentation file and raw file at the same time)

One option is to have slightly different menu options available based on single or multi-file selection. Another option is to maybe show the filename somewhere in the menu (like above "Open with").

Not sure I have a grasp on all the potential use cases here though!