New York’s tax authorities are intensifying their pursuit of wealthy residents attempting to flee high taxes by relocating to Florida, employing rigorous audits and domicile scrutiny that experts describe as relentless. As incoming Mayor Zohran Mamdani advances plans for a 2% city income tax increase on millionaires—pushing combined state and local rates toward 16.8% before federal levies—the state’s Department of Taxation and Finance is poised to ramp up enforcement resources. This crackdown comes amid accelerating outmigration, with nearly 900,000 residents departing between 2021 and 2024, per Empire Center analysis of Census data.

The so-called “six-months-and-a-day” rule—spending fewer than 184 days in New York—offers a false sense of security, tax attorneys warn. True domicile requires comprehensive proof, including updated driver’s licenses, voter registrations, bank accounts, and even relocating personal items like artwork or wedding photos. “New York is an extremely aggressive state when it comes to state income taxes. They do not like people leaving and they will do whatever they can to trap you back into the New York tax net,” said Christine Concepcion, an attorney specializing in tax matters, in a New York Post interview.

Even remote workers for New York-based firms face the “convenience of the employer” rule, taxing income if working from afar benefits the company. A National Taxpayers Union Foundation case involved a Missouri resident spared taxes only because he avoided the office entirely; a single holiday party visit would have triggered liability. Mamdani’s tax agenda, detailed in Gothamist, targets earners over $1 million, potentially channeling funds into more audits akin to practices in high-enforcement regimes.

Auditors’ Relentless Domicile Probes

Jon Hoff and Kathleen Ocorr-Hoff learned this harshly after purchasing a $1 million Naples, Florida, condo. Despite registering vehicles, updating voter rolls, starting a business, and moving belongings, they cashed New York paychecks and retained country club memberships—dooming them to a $60,000 tax bill upheld in court. Tax pros recommend extreme measures: securing Florida professional licenses, buying cemetery plots, or enrolling children in local schools to solidify residency claims.

“This isn’t something that you do overnight,” Concepcion emphasized. Construction firm owners, bound by site-specific work, face particular scrutiny, as noted by Randall Fox of Kirby McInerney. Meanwhile, posts on X from New York Post highlight public outrage over these tactics, with one recent thread decrying how enforcers “trap you” even after relocation.

Florida’s allure persists, but incomplete moves invite audits. Luxury publicist Melanie Holland observed in the Post that Palm Beach locals are being priced out by influxes of New York capital, yet auditors target those failing proper protocols. From 2018-2022, over 125,000 New Yorkers shifted to Florida, draining $14 billion in income, per a Citizens Budget Commission report.

Mamdani’s Tax Push Fuels Enforcement Surge

Mamdani, sworn in amid fiscal woes including a projected $12 billion city budget deficit, dismisses exodus fears. A Financial Times piece quotes him pressing ahead with millionaire taxes to fund affordability programs like free buses and child care. Critics, including Empire Center, warn his plans overlook outmigration’s toll—$3.8 billion in lost 2025 revenue, per National Taxpayers Union Foundation estimates.

Andrew Wilford of the foundation told the Post, “Everything we’ve seen so far from Mayor Mamdani suggests that he is not concerned with the trends… where people are headed out because they’re sick and tired of being overtaxed.” New York’s millionaire share has slid from 12.7% nationally in 2010 to 8.7% in 2022, despite absolute growth, Empire Center data shows. High earners’ mobility amplifies sensitivity to rate hikes.

Recent X sentiment echoes threats of flight: New York Post posts cite Andrew Cuomo vowing a Florida move if Mamdani wins, while Miami realtors report 166% inquiry spikes from wealthy New Yorkers. A National Desk report notes 5,000 business losses last year as firms eye low-tax havens.

Florida Migration’s Mounting Costs

The hemorrhage is stark: New York loses a resident every 2 minutes and 23 seconds net, Wilford calculates. A third of Florida-bound New Yorkers targeted Miami-Dade, Palm Beach, and Broward counties, slashing city adjusted gross income by $10 billion. Tatiana Tsoir of Linza Advisors, originally from Belarus, likened the strategy to socialist enforcement: hike rates, boost audits.

Experts counsel hiring specialized attorneys upfront, despite costs, to navigate dual-state rules. Florida’s no-income-tax regime draws billionaires fleeing even California’s proposed wealth taxes, as Fox Business reports rapid property buys for residency. Yet New York’s gaze remains fixed southward.

Outmigration erodes the tax base disproportionately, as high earners fund 50%+ of revenue. Wilford notes their resources enable swift relocation—selling homes, uprooting businesses. Mamdani’s Jacobin-defended plan assumes inelastic millionaire behavior, but evidence from The Daily Economy suggests otherwise: hikes spur exits.

Broader Fiscal Ramifications Unfold

Statewide, Hochul faces pressures as Mamdani pushes “tax the rich,” per Politico. NYC’s deficit evokes 2008 crisis parallels, with Mamdani leveraging it for hikes. Despite growth in raw millionaire numbers, proportional decline signals vulnerability.

Remote work complicates matters: auditors probe email logs, IP addresses, even gym memberships. Fox remarked, “If they’re New Yorkers, they have to pay the taxes like the rest of us.” Proving otherwise demands totality—safety deposit boxes, worship affiliations, licenses.

As 2026 unfolds, New York’s enforcers hold the upper hand, but sustained hikes risk a tipping point. Empire Center’s parsing of Mamdani’s blueprint forecasts strained budgets if flight accelerates, underscoring the high-stakes chess match between revenue imperatives and resident mobility.