How to upload a pdf file?

Why?  You can't upload that.   Are you trying to enter medical deductions?

Enter Medical under

Federal (Personal for HB)

Deductions and Credits

Then scroll way down to Medical

Then Medical Expenses - click Start or Update

You can only deduct the amount of unreimbursed Medical Expenses you actually paid over 7.5% of your AGI.  And then all your itemized deductions have to be more than the standard deduction to get any benefit (so you would only be getting the benefit of the amount that puts you over the standard deduction).  And since the Standard Deduction is increased more people will not need to Itemize.

For 2023 the standard deduction amounts are:

Single 13,850 + 1,850 or 65 and over or blind

HOH 20,800 + 1,850 for 65 and over or blind

Joint 27,700+ 1,500 for each 65 and over or blind

Married filing Separate 13,850 + 1,500 for 65 and over or blind

You do not enter things such as doctor's prescriptions.  You can enter your out of pocket amount paid for the prescription.   You cannot attach pdf's of documents to an e-filed return.   You only enter the amounts you paid for medical expenses.  Those will go to the Schedule A with your other itemized deductions.  If the IRS wants any details or additional information about something you entered, they will ask for it in a letter.

MEDICAL EXPENSES

The medical expense deduction has to meet a rather large threshold before it can affect your return. The amount of medical (including dental, vision, etc.)  expenses that will count toward itemization is the amount that is OVER 7.5% of your adjusted gross income. You should only enter the amount that you paid in 2023—do not include any amounts that were covered by insurance or that are still outstanding.  Of course, your medical expenses plus your other itemized deductions still have to exceed your standard deduction before you will see a difference in your tax due or refund.

To enter your medical expenses go to Federal>Deductions and Credits>Medical>Medical Expenses

2023 STANDARD DEDUCTION AMOUNTS

SINGLE $13,850  (65 or older/legally blind + $1850)

MARRIED FILING SEPARATELY $13,850  (65 or older/legally blind + $1500)

MARRIED FILING JOINTLY $27,700  (65+/legally blind) )  + $1500 per spouse

HEAD OF HOUSEHOLD  $20,800 (65 or older/blind)  + $1850)