Unfortunately ever since one of the updates this year it stopped working randomly. The screenshot above was taken after hours of having VS open at work. In the same file just before the screenshot was taken it reported one of the Types as missing and the quick fix worked - for the three you see it just never gave me the option, not even after closing and reopening the document.
I unfortunately can't give you a way to replicate this reliably but it happens to me multiple times a day where it just doesn't want to show the squiggly lines for missing imports.