TurboTax can only import information (documents) that brokerage firms like Vanguard make available on their end. It is not uncommon for taxpayers with multiple tax forms with the same broker, bank, insurance company, etc. to not be able to import all of their tax documents. As for your 1099-Rs, you will have to enter them manually. If you reported distributions from the same retirement accounts last year, most of the information for your 1099-Rs should have rolled forward from your 2022 return to your 2023 return.
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