Does a large condo special assessment count against my DTI when I go to buy a new house?

Yes. Plan on that assessment counting against your DTI until it's paid off. When you apply, the lender documents your HOA obligations, usually through a monthly statement or a letter from the HOA, and that paperwork discloses any outstanding special assessment. The current loan application (Fannie Mae Form 1003) also asks pointed questions that require you to disclose it, so an assessment doesn't slip past underwriting. Paying it off before you apply is the clean fix. Once the assessment is gone it no longer counts toward your DTI, though you still need to qualify for the new home's payment on its own. Since you have the cash to retire the assessment and cover what you need to close, that's very likely the path that works. There's a narrower angle to ask your lender about, and the rules differ by program: - Conventional (Fannie Mae and Freddie Mac): an installment debt with 10 or fewer monthly payments remaining may be excluded from DTI regardless of the payment amount, though an underwriter can still count a large payment that would strain you right after closing. - FHA: debts with fewer than 10 months remaining are excluded only when the combined payments of all such debts are 5% or less of your gross monthly income, and FHA does not allow paying a balance down just to get under the 10-month line. A portfolio lender writing its own rules might have flexibility too. Realistically, with a large balance still owed, most lenders will simply expect the assessment paid off rather than excluded, so plan around paying it down.