Quicken Classic for Windows, R65.29.
Many months ago I stopped trying to do a One Step Update from Vanguard and downloaded a .qfx file containing all recent account transactions. Then I would doubleclick on that and Quicken would import all of the transactions. The last successful import wa on Dec. 3. However when I tried the import on Jan 3, there were no errors, but transactions which documented reinvestments were all assigned to the ReinvInt activity category, when they should have been assigned to either ReinvLg, ReinvSh, or ReinvDiv category.
Since all of my accounts are set up for automatic reinvestment of dividends and capital gains, almost all of the downloaded transactions were reinvestment transactions, and I had to go into every one and edit it, filling in the amount and # of shares in the correct capital gain or dividend category, and deleting them from the Interest category. Because my wife and I have a lot of stocks and funds in brokerage, IRA, and Roth accounts, this problem changed the import from a straightforward process to one that dragged on for many hours, requiring a lot of attention to avoid typing errors.
Found nothing in the QFX log. Tried to make headway with the OFX log, but could not see any obvious differences between last month's import and the latest one. As far as I could see, transactions were correctly labeled in the memo field of the OFX log. A Quicken support person, blamed Vanguard. I'm sure a Vanguard support person will blame Quicken. Any help would be appreciated.