drop table #test go create table #test(Subject_E text) insert into #test (Subject_E) values ('Testing [OldMemberTableName]'), ('Testing [OLDMEMBERTABLENAME]') UPDATE #test SET Subject_E=replace(cast(Subject_E as varchar(max)) ,'[OldMemberTableName]','[Member]') select * from #testPlease check what is the database collation and do you have collation for that column. Script both database and the table.