Not sure how you have Vanguard set up in Quicken, but your exacerbating the problem by performing manual downloads from Vanguard to import. Quicken works flawlessly with Vanguard. For this to happen, you need to have Quicken mirror the accounts at Vanguard. Brokerage, IRA/Roth, mutual fund, whatever. If you have 5 Vanguard accounts, you need 5 in Quicken. These accounts should be set up using Add Accounts and identifying the correct type when logging in to the Vanguard website. The connection method is Direct Connect which will correctly download all transactions affected by any activity.JM has a nice write-up on how to perform an RMD here. https://getsatisfaction.com/quickencommunity/topics/faq-best-way-to-handle-distributions-from-ira
After reading some of the other reported cases where downloading was not happening, I tried to do a manual download and then import into Quicken. On the Vanguard site, I selected the All funds into one account, then 30 days and selected the four funds that make up this IRA account in Quicken. When I imported the resulting file, I was prompted four times to identify which Quicken account to use. At the end, I got an error message OL-362-A (The financial institution data is for an account that does not exist in the Quicken Data File). Can anyone help me understand how to resolve this issue?