What is the smartest way to gradually move my US investments to India over several years?

Rather than a single large transfer, most cross-border planners suggest a phased approach tied to your tax situation. Sell US taxable-account positions strategically to manage capital gains, ideally using low-income years to harvest gains at the 0% or 15% federal rate, then remit the after-tax dollars to your NRE account (fully repatriable) or reinvest in India. Keep tax-advantaged US accounts (401(k)/IRA) in the US wrapper and draw them in retirement rather than liquidating early and paying penalties. Time transfers to favorable USD/INR rates where you can, and stagger them to avoid a single-year tax spike in either country. Coordinate the sequence with both a US preparer and an Indian CA. Model the timeline with the Return to India Calculator at wealthserene.com/tools/return-to-india.