File first. Pay what you can.

Yes — this is the most important thing in the whole guide. The penalty for failing to file is typically much larger than the penalty for failing to pay, so filing on time or as soon as possible reduces the damage substantially even with nothing attached. Most collection options also require you to be current on filings, so unfiled years block the door.

Rarely, and not because you negotiated well. Offers to settle for less than owed are accepted in a minority of cases, and eligibility is driven by a formula using your income, allowable living expenses and asset equity — the numbers decide, not the argument. Firms advertising guaranteed settlements for pennies and charging large upfront fees are a well-known consumer trap.

Start from what's genuinely left after essentials and other debts, and propose something you can sustain rather than something optimistic — defaulting is worse than starting lower. In the calculator, $550 a month clears a $14,000 balance in about 28 months once charges are added; adding $200 more brings that down to 20. If nothing is left, that's a hardship situation, not a failure.

More than most people realise. The Taxpayer Advocate Service is independent and free and exists for unresolved problems and hardship. Low-income taxpayer clinics provide free or low-cost representation. For paid help, use a CPA, enrolled agent or tax attorney — and be aware of impersonation scams: the IRS does not demand payment by gift card or threaten immediate arrest by phone.

Usually on the next year's taxes, not this year's. A new balance can break the agreement you just set up, so if you're self-employed or have untaxed income, set estimated payments or withholding now. And if your circumstances change, contact them before missing a payment rather than after — agreements can often be revised, and hardship status exists if paying becomes impossible.