I have been using Quicken and TurboTax for all my finances and taxes for at least 10 years. For all of those years, I have used the procedure that Intuit recommends for capital gains exporting which is described here:
https://www.quicken.com/support/how-transfer-tax-information-quicken-turbotaxFor all of those years, I trusted that I was accurately reporting my capital gains but I am now losing confidence in that process.
When I attempted to do a capital gains export this year, I saw some fairly large capital gains I wasn't expecting. That caused me to start looking deeper to see what was wrong. The most obvious problem I found was that there were a number of share conversions that had a zero cost basis because the cost basis wasn't transferred over during the share conversion. I was able to manually fix that by going back and finding all the zero cost basis transactions and fixing them.
Then I tried to match the capital gains report data against a capital gains report from my financial institution and only a few of the capital gains/losses matched. I download all my transactions directly from financial institutions almost daily and I put a lot of work into regularly reconciling all of my accounts to be sure that the Quicken data agrees with the data from the financial institutions. I am sure that all the assets match and the valuations also match - how is it possible for the capital gains to be so far off? I need to be able to trust this capability in Quicken because the alternative of entering all these transactions manually is so time-consuming and tedious. Any help will be greatly appreciated.
Thanks,