I decided to try TurboTax 2020 this year after getting fed up with bugs in H&R Block’s software. It seems TurboTax’s quality isn’t great either. I kept getting unsuccessful import errors when trying to import H&R Block 2019’s PDF.
The trick, I discovered, is to prune down what H&R Block puts in the PDF:
- Open H&R Block and pull down the File menu.
- Click Print, and deselect everything except for Forms to Submit.
- Print to PDF. The PDF that’s generated will import successfully into TurboTax.

I guess the TurboTax importer was getting confused by the cover pages and/or supporting forms/worksheets. You’d think Intuit would test this. (and perhaps revamp their importer or at least include a useful error message)
Other annoyances I’ve found with tax software this year:
- I had to wait until mid-March 2020 to file, due to TurboTax bugs in ESPP calculations.
- TurboTax HDHP/HSA weirdness thinking spouse had a break in coverage when they didn’t.
- I re-downloaded H&R Block 2019 from Amazon and tried to run it on my M1 Mac. It refused to open, even using Rosetta 2. No error messages, it just won’t open. Thankfully, I had an old Intel Mac I could use to open it and perform the above steps.
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