My CSA 1099-R Box 1 total includes deductions for health insurance (Box 5), dental and long-term care premiums. Do I show these other two as itemized medical deductions?

If entered on the 1099-R screen, the program will carry the amount to Schedule A Itemized Deductions.

When you enter the 1099-R, enter the amount in Box 5. Enter only the dental unless the premium for long-term is within the tax year 2024 limits.

The limits are 

Age 40 and under $470

Age 50-41 $880

Age 60-51 $1,760

Age 70-61 $4,710

Age over 71 $5,880

TurboTax will ask if this was for a Roth IRA contribution or health insurance.

Select "health Insurance".

If the premium for long-term is within the limit, and you have two numbers in box 5, you van add the amounts and enter as one number. 

If the premium is over the limit, enter only the amount for dental on the entry screen for Form 1099-R and enter the ling-term care expense under

Deductions & Credits 

Medical

Medical Expenses 

Scroll through until you get to the screen to enter long-term care premiums. 

Because of the potential limit, that type of premium needs to be reported on that screen. 

You have the option of reporting the expenses either way, (under Medical Expenses or on the 1099-R screen)  but not both.