I had an 401(k) that allowed both Roth and Regular payroll deductions. Similarly to what you are saying it held all investments in the "same" account. While it might have the same account number or look like the same account the FI overseeing the account is actually tracking them separately through some internal mechanism. So while it is showing XYZ Roth and XYZ Regular as 2 positions for XYZ stock the stock is technically the same (i.e. same symbol, same CUSIP, etc). So when your FI sends the information to Quicken it is only sending information for the stock (XYZ), the number of shares, price etc and thus Quicken cannot discern the difference.What I did was create 2 separate securities with the same ticker symbol in Quicken (XYZ) with different names (XYZ Roth and XZY Regular) and then when the information downloaded I made sure to separate the transactions by the two version of the same security.Don't ask me with these FIs don't actually use 2 separate accounts for the Roth and Regular. Best of luck.