In my application, users will have a list which display their files and each item has its own send button. They have option of sending the file via FTP or E-Mail. Whether i can ask the user to select the sending via option through radio buttons in settings or i can ask them for each file while clicking the send button.
You can change the interface for the group interaction. It is not only allows to minimize user actions but also makes interface visually more clear. Also if the sending is not performed often, you can hide options in the dropdown list, which appears on
If sending is often operation and probability of choosing FTP or Email is equal, there should be two separate controls for this. If some option has great preference there could be one control for sending and optional switching control for other sending option.
You could use a
The files should be presented as a list where the user can perform the multi-select with Ctrl or Shift + mouse click instead of a list of checkboxes that have to be clicked individually.
By the way, is the application a web application or a desktop application? Overriding the right mouse click might not be an option in the case of a web application (and there are also issues with touch devices).
(Obviously you need to add to the context menu only the options you intend to provide, my screenshot is just an example)