You need to enter the self-employed health insurance premiums in the same section where you enter your Schedule K-1 (Form 1120S). 

1. Go to the Federal Taxes category.
2. Go to the Wages and Income subcategory.
3. Choose the option "I'll choose what I work on".
4. In the list "Your 2016 Income Summary", find the section labeled "Other Business Situations".
5. Click start or update on the item Schedule K-1.
6. Go into your Form 1120S K-1.
7. Continue through most of your entry screens until you reach a screen labeled "Describe the Partnership" that has a list of items.
8. On this list, check the box labeled "I personally paid health insurance and/or long-term care insurance premiums for myself and my family and this S corporation paid me wages." and hit continue.
9. Continue to the next screen where you will enter your medicare wages (box 5 of your W-2) and the health insurance premiums.

I was having the same problem. To get the Line 29 deduction without the Itemized deduction, you need to do the following.

• When you enter your k-1 info check the box about personally paying the health insurance. Then enter the appropriate wage info, but enter zero for the amount paid for insurance. This is if you received a 1095-a.
• Later after you enter the 1095-a with your insurance detail, open the actual Turbo tax form 1095-a.  At the bottom of the actual form there is a section to link the form to a business.  Choose the type of business to link it to and the options should come up to select your business information.  Once you do this, Box 29 populates and the itemized deduction goes away.
• Good Luck.

I do not have the "Other Business Situations" options. I have tried both TT Premier and TT Home and Business for 2019 but can find no way to enter the 2%Shareholder Health Insurance deduction.  I can override the Schedule 1 line 16 field with the amount but get errors and won't be able to efile with an error?

Try navigating to that section in the program by:

1. Logging into your account

2.Click 'continue my return' or 'continue where I left off'

3. On the left side of the screen you will see Tax Tools, click that

4. Click Tools

5. Click Search 

6. Type in ' 2% shareholder health insurance' 

7. Click go, answer the questions and follow the prompts 

sadly this last instruction does not work for the desktop app (I'm on a Mac). Please let us know how to do it there for the 2019 tax return.

You need to enter the self-employed health insurance premiums in the same section where you enter your Schedule K-1 (Form 1120S). 

1. Click start or update on the item Schedule K-1.
2. Go into your Form 1120S K-1.
3. Continue through most of your entry screens until you reach a screen labeled "other situations"
4. On this list, check the box labeled "I personally paid health insurance and/or long-term care insurance premiums for myself and my family and this S corporation paid me wages." and hit continue.
5. Continue to the next screen where you will enter your medicare wages (box 5 of your W-2) and the health insurance premiums.

thank you for the quick reply.

"Other Situations" never showed up for me before. Now I checked "I received an amended K-1 for this S-Corp" (even though I did not receive that) and "Other Situations" with the health insurance entry showed up. Not sure if that was the solution or I had previously been repeatedly sucked into a time warp at that spot. 

anyways  solved now. thank you.

WAIT a minute ... why did you indicate you got an amended K-1 form ?   That was not needed.   You may wish to either review the K-1 entry screens  or   delete the K-1 and start again from scratch. 

yes, I know. Was not needed. I unchecked it again on the form itself and the health insurance correction remained. So it looks like this challenge is solved.

That said, I know now that our CPA made other mistakes and I will enter an amended K1 eventually anyways.