I've been filling out Form 2210 (including Schedule AI) for years now, and I definitely don't consider it straightforward . I use H&R Block, but I can't see how TT could make it so much easier considering that tax programs don't know the exact timing of the dividends, capital gains distributions, interest income, and other sources of income one receives unevenly throughout the year until you input all that data. And IME brokerages don't provide that tax-quarterly breakdown, either. You have to download all the data and manipulate it yourself to get the "income by tax period" data required for Form 2210 Schedule AI. I suppose it can be fairly straightforward if the vast majority of one's income is spread evenly throughout the year and there's just one uneven income event that happens in Q4... but that isn't my situation at all. My income has always varied a lot throughout the year due to cap gains, dividends, and "options premiums" income. It has long been a pet peeve of mine that brokerages only provide a breakdown of investment income along calendar quarter lines and not "IRS tax quarter" lines.