I suggest you have real world securities mismatched with your Quicken securities. For each Quicken security that is either getting picked incorrectly or not getting picked when it should be, edit the security detail and uncheck the box about Matched with online security. Also make sure the security name is sufficiently unique in the first 16 or so characters. At you next download from Vanguard, you should get the opportunity to correctly match the security Vanguard is sending to the right one in your Quicken file.