I'm using the desktop version of TurboTax Premier. I used TT last year so when I started this year's return it read and pre-filled some fields from last year's return. Last year I had one 1099-DIV entry, so when I first entered this year's 1099-DIV section, last year's entry was present. I used Edit to open that entry which led to the Import page. I chose to Hand Enter. It advanced to the Entry form with the brokerage field pre-filled. I filled out the amount fields.
At this point I don't remember exactly which forms it presented, but I had a second brokerage to enter so I completed the first brokerage and ended up back on the initial 1099-DIV page with my newly entered number for the first brokerage correctly displayed. I then chose the Add New and advanced into the Import page again. I again chose to Hand Enter, but in addition, I checked the Do Not Show This Page Again checkbox and advanced to the Entry form where I filled in the information for the second brokerage. The one wrinkle, which I don't think is important, is that on this second brokerage entry I had to open the Other Additional Fields area because that brokerage had an entry for field 5 in addition to the 3 normal fields. I doubt this is important because when I enter this brokerage as the first one instead of the second, it correctly shows up and it's the other (second) brokerage data that is discarded.
I was now done with 1099-DIV and chose Done with the 1099-DIV section and went to the Summary of Income page where the Dividends field incorrectly showed only the total for the first brokerage, but didn't include the second. I chose to go back into the 1099-DIV section and saw that only my first brokerage data had been saved. I've since repeatedly tried to enter my two brokerages, but only the first entry is saved. I've deleted both and re-entered - no difference. I've reversed the order - only the first one entered is saved.
I suspect the problem may be related to checking the Don't Show Me This Again box on the Import page, but after checking that box earlier, I no longer get shown that page. I have not found a way to reset that checkbox from inside TurboTax menus nor seen a reference to doing that in the online Help system.
One additional hint - while trying to re-enter the second brokerage, after filling in the fields on the Entry page, I chose Back instead of Done to see what the 1099-DIV page showed and it correctly showed the second brokerage entry with it's amount fields. However, clicking Done from that page also discarded the second brokerage entry. It doesn't make sense that checking the Don't Show This Again would result in this information-discarding behavior, but sometimes bugs can be weird. It's the only thing I did that seems in any way unusual and I have no doubt that the 1099-DIV entry section works correctly for just about everyone. Otherwise lots of people would be complaining about this.
