1) No downloads are automatic...you must initiate from withing the program .
2) Free cannot download anything...PLUS or Deluxe would be minimum, and perhaps Premier dependent on exactly what financial forms you are attempting to import.
3) SSA-1099 has never been available in the past for a tax file import...(they could change that someday...but haven't seen that they allow it this year)
4) Vanguard?...depends on what form types, but they do not have their specially-formatted tax files available for most users yet....even if they have their PDF forms available now. Probably will be available in next week..... or three.
5) OPM CSA/CSF-1099-R Downloads?...not sure I've ever seen those available as a tax file import either...but I could be wrong.
Most tax forms are not available for tax importation yet...some W-2 forms are, most 1099-R-type forms are not...IF (Big IF) IF they are allowed at all by the provider.
____________*Answers are correct to the best of my knowledge when posted, but should not be considered to be legal or official tax advice.*