Conditional formatting - including flag images

I'm working on a report that I want to include conditional formatting resulting in flag images displaying in a column. Can you have more than one image in a column?

Currently I have 3 conditional cases that should potentially result in a maximum of two flags displaying, but I only seem to be able to have 1 display. In my test case, for the project that should result in 2 flags, whichever set of code is first is the only flag I see.