Here’s a summary of my bad experience with trying to import my 1099s from my broker this year using Turbotax Premier 2024 desktop edition. I’m running on macOS Sequoia 15.3.2 (the latest as of this writing). The TL;DR is that I did many, many things to fix my problem but ultimately used a friend’s computer who was also running Turbotax Premier to download my 1099s. He happened to be running Windows, and fortunately the files created by macOS and Windows version of TT are cross-compatible.
Here’s more detail. First some background. I’ve been using TT Premier for at least ten years and have been downloading my 1099s from my broker for years and years with no troubles. I’m a sophisticated Mac user (retired electrical engineer).
I bought TT from Amazon and downloaded the disk image and dragged the application into my Applications folder per instructions. When I tried to download my 1099s after my broker said they were ready, I went to the “import from broker” screen, I entered the user name and password for my broker along with my SSN and clicked “Continue.” A dialog saying “establishing secure connection” popped up with a bouncing progress indicator. About five seconds later, my Mac beeped, the dialog went away, and I was back at the import screen. No error message showed.
I’ve listed below all the things I can remember that I tried to solve my problem, but none of them worked. The only partial success I had was installing TT 2023 (yes, last year’s) onto my Mac, and that was able to grab my 2024 1099s from my broker with no difficulty. However, they were useless to me as there was *no way* to transfer all the details from a 2023 tax file to my 2024 tax file.
Here’re all the things I tried that did not work. All these took place over the course of about a month.
* Spent two hours with Intuit phone support agents (two different times). The second agent shared my screen and verified I was doing everything correctly, and he ended up saying “it’s broken.”
* Changed the password for logging into my broker to a shorter, simpler password without special characters.
* Redownload and installed TT.
* I know my broker has to have its “share with third parties” feature enabled, and it has been, but I disabled and re-enabled it just in case it was stuck some how.
* Booted my Mac into Safe Mode.
* Cleared my browser’s cache at the request of the Intuit support agent. I thought this was useless since I am use TT desktop and not online, but I did it anyway.
* Installed TT on my old Mac and tried the import.
* Created a new user on my Mac.
* Looked for log files to give me some indication about the nature of the failure. I never found any, and the Intuit tech support agent said he didn’t know of any. There really should have been some kind of error message.
* On each TT version update, I’d try to import the 1099s again.
* I’ve searched the TT and Apple support forums for others having a similar problem, and I haven’t found anybody with this exact symptom.
I agree with the Intuit support agent: it’s broken, at least for me. At this point I’m not really looking for a fix but wanted to let folks know.
