Three conditions make a conversion compelling. First, you expect a higher tax rate later than today — paying now at the lower rate wins. Second, you can pay the tax from outside savings, so the entire converted balance keeps compounding tax-free; paying tax from the conversion itself shrinks the Roth and, under 59½, can trigger a penalty on that portion. Third, you have a long horizon for the tax-free growth to work.
The best timing is usually a low-income year: early retirement before Social Security and RMDs begin, a career gap, or a sabbatical. Converting then fills lower brackets cheaply. Be careful of second-order effects — a large conversion can push you into a higher bracket, increase the taxable share of Social Security, and raise Medicare premiums via IRMAA two years later. Many people convert in measured annual chunks rather than all at once.