You aren't required by the program to enter your medical deductions to qualify the HSA. While it is true that the program wants you to enter all your medical expenses, then enter all your insurance and HSA reimbursements (on the theory, I suppose, that the computer is smarter than the taxpayer); it isn't required for the HSA. Checking the box that says "I used all the HSA for medical expenses" is sufficient.
Additionally, if the taxpayer here enters all $10,000 of medical expenses as itemized deductions, that will result in an illegal excess deduction. The only expenses you can deduct on your 2019 return are expenses actually paid to the provider in 2019. However, HSA reimbursement can go farther back, as long as the expenses were not previously reimbursed from some other tax-free source. In particular, this taxpayer's income is $83,000 according to them. They paid $7000 in 2019 and $3000 from 2015-2018. Using the 7.5% floor on medical expense deductions, they would normally have an $800 deduction for 2019, but claiming all 2015-2019 expenses on the 2019 return will give them an excess and unallowable deduction of $3800.
