it appears that jtreg doesn't support having multiple entries for the same test in one problem list (see CODETOOLS-7902481).
the following occurrences in langtools problem list should be merged in order to achieve the expected behavior:

test/langtools/ProblemList.txt:tools/javac/annotations/typeAnnotations/failures/CantAnnotateStaticClass2.java 2
test/langtools/ProblemList.txt:tools/javac/annotations/typeAnnotations/failures/CantAnnotateStaticClass3.java 2