Clicking "Attach files" in the Get help from an expert > Email support, replaces any previously attached files.
Confusing experience when attaching multiple files:
The form accepts multiple files, but they must all be selected and attached at the same time — adding a second file later replaces the first.
The files also need to be in the same directory. On a Mac, I couldn’t multi-select files from different directories (unless I used the Recents view).
Allow users to attach multiple files one at a time, without replacing previous files
Ability to remove previously attached files