How do I know if I need to upload a tax 1095A form?

If you have health insurance from healthcare.gov you do need to enter a 1095A but you cannot "upload" it.   You have to key it in by hand.

Yes, you need to get your 1095-A from Healthcare.gov and enter it in TurboTax. 

Here's how to do that in TurboTax Online:

1. Open your return
2. Select the down arrow to the right of Deductions & Credits, then Review/ Edit.
3. Select the down arrow to the right of Medical.
4. Select Start or Revisit next to Affordable Care Act (Form 1095-A).
5. Answer the questions and continue to enter the details from your Form 1095-A.