The eligibility rule is the most useful thing on this page, because it excludes the person who most obviously needs help. The IRS lists two qualifying situations and no others: "a job with an employer (W-2)" or "a pension or annuity with federal income tax withholding." It adds that "you can't use this tool if you have nonresident status for U.S. tax purposes," and points those taxpayers to Notice 1392, "Supplemental Form W-4 Instructions for Nonresident Aliens." A freelancer with no wage job has nothing for the tool to adjust, and reaches the same destination through estimated taxes instead. The tool does handle self-employment income alongside a wage job, which is a different and common case, and asks for payment records to do it.
The output is a form rather than advice, and it covers pensions as well as wages. Form W-4P is the withholding certificate for periodic pension and annuity payments, and a retiree adjusting withholding on a pension is using a different document from an employee adjusting withholding on a paycheck. The estimator will produce whichever is relevant, pre-filled, to be handed to the payer.
The privacy statement is unusually direct and answers a real worry. In the IRS's own words, "the estimator doesn't ask for personal information such as your name, Social Security number, address, or bank account numbers. Your information won't be saved or shared with the IRS. If you close your browser window, your responses will be cleared." That last sentence has a practical edge as well: nothing is stored, so a session interrupted halfway has to be started again.
What the session requires is a small pile of documents. The IRS asks for the most recent pay stubs for each job, pension or annuity, and for a spouse's too where a joint return is expected. Anyone with other income, or who expects to itemize, is also told to have last year's federal return, payment records for self-employment, gig work or Social Security, and records of the expenses they plan to claim. The IRS puts the whole exercise at about 25 minutes.
The timing advice has a trap in its last sentence. The IRS says to check withholding every January, and again after a new job or other paid work, a major income change, a marriage, divorce or separation, a birth or adoption, or a home purchase. It then adds: "If you change your withholding during the year, you may need to update it again in late December to withhold the right amount next year." A mid-year correction is sized against the pay periods left in that year. Left in place, the same entry runs for a full year and over-corrects, which is why the December check is not optional housekeeping.