Make sure that your conditions really are like the following, it is different when you comebine (... or status =="gold") and @status == "active
or if you write (... OR @status == "silver") or (status =="gold" and @status == "active )
%%[
var @status, @booleanField, @subjectline
set @status = [status]
set @booleanField = [nameOfTheBooleanFieldInTheDataextension]
IF (@status == "bronze" OR @status == "silver" OR @status =="gold") AND @booleanField == "active" THEN
set @subjectline = "A"
ELSEIF (@status == "bronze" OR @status == "silver" OR @status =="gold") AND @booleanField != "active" THEN
set @subjectline = "B"
ELSEIF @status == "trial" and @booleanField == "active"
set @subjectline = "C"
/* Best Practise would be to always include all possible conditions therefore the ELSE condition should be here */
ELSE
set @subjectline = "D"
ENDIF
]%%
%%=v(@subjectline)=%%
More for subjectline can be found in this post