Entering the health insurance amount from box 5 on a 1099-r

Where is this happening? When you enter the 1099-R? In the Federal Review? In a state review? Someplace else?

When TurboTax asked if the amount in box 5 was insurance or something else, what did you answer?

How much did you enter in box 5?

I ask these questions because I am having difficulty reproducing your issue.

I enter the amount in box 5 correctly.  But then 4 screens later, there is a Question asking how much of the amount in box 5 is insurance premiums.  The entire amount is premiums, so I enter that total again, and when I'm finished with that financial institution's income, it comes back with a "Needs Review" red button.  When I go to review it, it's the same Q which is now blank.  I've spent several hours on the phone with TurboTax reps, and finally last night someone told me that there is a glitch with the online version when entering an OPM 1099-R, which ours is.  So until, and IF, it's fixed, I can't complete my taxes using TurboTax unless I want to download the program and re-enter everything!  To say I'm annoyed is an understatement!

"when I'm finished with that financial institution's income, it comes back with a "Needs Review" red button"

So was this in the Review, or in the 1099-R interview?

On my test, I created a 1099-R from the OPM, but I did not get the same results (the Needs Review was for other reasons).

After you entered the 1099-R from the OPM but before you got the Needs Review, did you look at your 1040 to see if the income from the 1099-R was there? Was the amount reduced by the box 5 entry?

Can you see your output forms (i.e., have you paid for the return)? I want to know if the amount you originally entered in box 5 appeared on Schedule A as a medical expense.

I am having the exact same experience, exactly as you described!

I'm having the exact same issue as described above.

tt refuses to accept amount from box 5 withheld for health insurance.  

I have the same issue have spoken to Turbo Tax support to no avail...when do we think this will be addressed?

I was not given any timetable for resolution.  I think the problem is only on the online version and might be ok on a downloadable version.  I was hesitant to spend the money not knowing if the downloadable version truly would work.  I was even told if it was solved after 4/15 that I could always file an extension!!  Very disappointed and I ended up going another route.  I love TurboTax and hope this gets resolved if not this year, at least for next year.  

@corkery-taxes @Tax2025a @jimlois1 

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:

1. Sign into your online account.
2. Locate the Tax Tools on the left-hand side of the screen.
3. A drop-down will appear. Select Tools
4. On the pop-up screen, click on “Share my file with agent.”
5. This will generate a message that a diagnostic file gets sanitized and transmitted to us.
6. Please provide the Token Number that was generated in the response.

TurboTax Desktop/Download Versions:

1. Open your return.
2. Click the Online tab in the black bar across the top of TurboTax and select “Send Tax File to Agent” *
3. 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.
4. 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”)