I have had a similar experience. It seems that Quicken 2017 for Mac double-counts some transactions. For example, if I have added cash to my IRA and then bought mutual funds or stock, the software sometimes totals both the added cash and the value of the funds I invested it in. I couldn't make sense of what was going on, so I called Fidelity and they walked me through a process that I've since done several times. You just delete the inaccurate accounts from Quicken, and then set them up again making sure you use the correct Fidelity connection, which is labeled that it's for Mac users. Then Quicken and Fidelity will match. This situation makes me very conscious of making sure that the sum shown in Quicken is the same amount reflected in my Fidelity account.