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So, I went ahead and told it that I wanted to upload during the Wages & Income section and uploaded a 1099R that I had previously uploaded. It processed the upload and went through asking me the questions about the document.

 

So, then, the question is, what's the point of uploading ALL of my documents, which are now sitting in the Documents area, if it's going to ignore them and asked me to upload them again, one at a time, in order to ingest them into Income?

 

You can take this as a rhetorical question and ignore me. This is a matter for TurboTax developers to address.