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I would like to take a deeper look at this. However, I need a diagnostic file which is a copy of your tax return that has all of your personal information removed. You can send one to us by following the directions below:   TurboTax Online:   Sign into your online account. Locate the Tax Tools on the left-hand side of the screen. A drop-down will appear. Select Tools On the pop-up screen, click on “Share my file with agent.” This will generate a message that a diagnostic file gets sanitized and transmitted to us. Please provide the Token Number that was generated in the response.   TurboTax Desktop/Download Versions:   Open your return. Click the Online tab in the black bar across the top of TurboTax and select “Send Tax File to Agent” * This will generate a message that a diagnostic copy will be created.  Click on OK and the tax file will be sanitized and transmitted to us. Please provide the Token Number  (including the dash) that was generated in the response.   *(If using a MAC, go to the menu at the top of the screen, select Help, then, “Send Tax File to Agent”)  

@Polkadot1 I hear you. On one hand, it is nice of TT support to get in touch and chat about their bug. However, the statement    "The tricky thing with these issues is that they are very hard for us to recreate ... Things sometimes just take time."  sounds hollow in this case. Clearly, to verify that data import works at all, the TT developers, or their SQA group must have access to at least one financial institution with synthetic / dummy logins and synthetic accounts. And clearly, they have access to more than one such account at that financial institution, to verify several 1099-R and 1099-DIV will download correctly.  With this is place, all they have to do is follow the simple steps we all describe - repeatedly - in this thread. It is NOT rocket science. It is NOT "very hard to recreate".   Well-meaning as the tech support personnel might be, my response would have been "let me write down for you the trivial use case, and the corresponding test case procedure, and if the SQA team cannot follow it, please find another SQA team who can".   We, the software professionals know better than to accept such boilerplate statements.   Peace  

Make sure that you have installed your state return because that can cause issues when transferring.    Then:    1. In Desktop, start a New 2025 return, then look for a prompt to transfer last year and choose Skip/Continue without transferring for now. Retry Continue From TurboTax Online from the Desktop Home screen. If not shown, close and relaunch Desktop and look for it again. 2. If the Online import option won’t appear or loops Log out of TurboTax Online, clear your browser cache, and try again in a fresh incognito/private window (Chrome/Edge/Firefox). This resolves stuck “Continue” loops seen during transfers. 3. Fallback: You can recreate the return in Desktop. Since you were able to import 2024, you won't have the 2025 data, but it prepopulates carryovers and identities so you can finish 2025 in Desktop.

This is EXACTLY the situation I'm in and it's driving me crazy. Been using TT since the 1990s and this is the first time I am having problems. It is exactly as you describe, but with Wells Fargo Advisors. NEVER had a problem importing in the past. I really do want a refund  from TT this year because I pay for this basic functionality, I should not have to go and manually move numbers from 2024 to 2025.  Hoping TT sees this and fixes the issue ASAP.  I've also tried the suggestion of the experts above to no avail.

You can enter business expenses in TurboTax by uploading a spreadsheet or connecting to your bank or credit card company.  To do so in TurboTax Online:    Go to Federal, >> Income >> Self-employment income After entering your income, you will see "Time to add expenses" That page has link to information about uploading a spreadsheet or connecting to a bank. On the next page you can select the method you want to use:  Enter manually, Upload a spreadsheet, or Connect to a bank. Make your selection and continue After working all the way through the self-employment step-by-step, sometimes you cannot access the upload page.  If this occurs, you made need to delete your business and re-enter it.   

TurboTax has a glitch that is presenting the entering of expenses.  They are aware and working on it.   But as others have said, you can just delete the 1099-Q.  The 1099-Q is  only an informational document. The numbers on it are not required to be entered onto your (or your student's) tax return. The interview is complicated, even when it's working  and it's easy to make mistakes. Avoid it if you can and you probably can.  You can just not report the 1099-Q, at all, if your student-beneficiary has sufficient educational expenses,  to cover the distribution. When the box 1 amount on form 1099-Q is fully covered by expenses, TurboTax will enter nothing about the 1099-Q on the actual tax forms. But, it will prepare a 1099-Q worksheet for your records (you don’t need it). You would still have to do the math to see if there were enough expenses left over for you to claim the tuition credit. You also cannot count expenses that were paid by tax free scholarships. References: On form 1099-Q, instructions to the recipient reads: "Nontaxable distributions from CESAs and QTPs are not required to be reported on your income tax return. You must determine the taxability of any distribution."  IRS Pub 970 states: “Generally, distributions are tax free if they aren't more than the beneficiary's AQEE for the year. Don't report tax-free distributions (including qualifying rollovers) on your tax return”. "IRS Publication 970, Tax Benefits for Education states: If the entire 1099-Q went to qualified expenses, room and board, tuition, etc; then, you do not need to enter the form." 

Clearly the Tax Expert did not fully understand the user's question. If an option is sold short, then bought back, the two fields appear:  Proceeds and Cost basis. But if that same option expires rather than being bought back (a common occurence), the Proceeds field is omitted, which is an error in TurboTax.  In this case, it could have been dealt with by allowing a negative Cost basis, which is technically the correct way to report, since it's a short position.  But the software prohibits negative values, so another error in the software. So, stating that TurboTax treats options just like stocks is ludicrous.  Why have the option choice at all? This bug needs to be corrected.  It's been around for a long time, apparently.

When I look on the schedule A it does show the medical expenses which are far in excess of the 7.5% but for some reason the program is not applying this, just states that I should use a standard deduction which is incorrect.

In the federal taxes, in the Income section, under Retirement Plans and Social Security, click Start for IRA, 401(k), Pension Plan Withdrawals (1099-R).  You will be able to import or enter your 1099-R information and TurboTax will guide you through the entry to get the income reported correctly.  If you have additional questions, please ask!     See Where do I enter my 1099-R? - TurboTax Support - Intuit