Recording investment income in taxable and non-taxable categories (3 Legacy Votes)
I am a new user of Q Mac 2018 and find all dividends (taxable and non-taxable) are in one income category. Using the "Tax Report" does not accurately reflect the true nature of the dividends.
It is a hassle but I set up a unique category for taxable dividends (i.e. 185 Dividends-T) and another for non-taxably from IRA accounts, etc. (i.e. 186 Dividends-NT). To record a dividend in any investment account use "Miscellaneous Income" in the Type box and type in the unique category (185 for a taxable dividend) in the "Category" box opposite the amount box. This will segregate the dividends in the Reports.
Quicken should expand the options for recording different types of investment income; however, until then, this approach seems to work for me.
It is a hassle but I set up a unique category for taxable dividends (i.e. 185 Dividends-T) and another for non-taxably from IRA accounts, etc. (i.e. 186 Dividends-NT). To record a dividend in any investment account use "Miscellaneous Income" in the Type box and type in the unique category (185 for a taxable dividend) in the "Category" box opposite the amount box. This will segregate the dividends in the Reports.
Quicken should expand the options for recording different types of investment income; however, until then, this approach seems to work for me.
1

Comments
Currently, Quicken Mac will do any reinvested dividend as ONE transaction, and as you noted will not distinguish between taxable and non-taxable dividends.
What I've done to alleviate the double entry is retain the "one transaction" of reinvest dividend and then create two separate reports in Quicken Mac.
One report is for taxable dividends and capital gains, the other is for tax deferred (non-taxable) dividends and capital gains.
I segregate the two by customizing and selecting only taxable accounts in one and non-taxable accounts in the other.
I even have a third report that has both taxable and non-taxable accounts.
Just an alternative way to handle things.