🛒 What your AI can buy, what your bill got wrong, and what Thanksgiving can pay you

The income number behind your 2027 premium, a 60-day billing clock and Thanksgiving cash

This Week’s Money Map:

  •  đŸ’¸ Your 2027 health premium looks outrageous? Check the income behind it

  • 🧾 Found a billing mistake? Put the dispute in writing

  • 🦃 Thanksgiving week pays people who plan now

  • 🤖 Before AI shops for your gifts, check what it can see and spend


💸 Your 2027 health premium looks outrageous? Check the income behind it

Billing mistakes topped our latest reader poll. This week, we’re starting with a number that can change your health insurance bill: the income estimate on your Marketplace application.

Premiums are rising. KFF reports that average benchmark silver premiums are up 13% for 2027, before subsidies. That doesn’t mean your own payment will rise by the same amount. Your plan, location and premium tax credit all affect what you pay.

Your savings depend on this year’s estimate

Marketplace savings for 2027 are based on your expected 2027 household income, not just what you earned last year.

Your latest tax return is a starting point. For Marketplace purposes, modified adjusted gross income equals adjusted gross income plus tax-exempt interest, nontaxable Social Security benefits and excluded foreign income. Then account for expected changes, such as a raise, retirement or income from a side business. For self-employment, estimate profit after business expenses, not total sales.

An old estimate can leave you paying too much each month or collecting a bigger advance tax credit than you qualify for.

Check who’s in your household

Your Marketplace household usually includes you, your spouse and the people you expect to claim as tax dependents, even if some don’t need coverage.

A baby, divorce or change in who claims a child can affect eligibility. Follow the application’s household questions rather than counting everyone who shares your address.

The repayment rules have changed

Starting with tax year 2026, no income-based cap limits repayment of excess advance premium tax credits. If you receive more than you’re entitled to, you must repay the full excess when you file your federal return. For 2027 coverage, that reconciliation happens on your 2027 return, filed in 2028.

Under current rules, household income above 400% of the federal poverty level makes you ineligible for the federal premium tax credit. For 2027 coverage, that threshold is $63,840 for one person or $132,000 for a family of four in the contiguous states and Washington, D.C. Alaska and Hawaii have higher thresholds. State assistance may follow different rules.

Don’t let auto-renewal do the shopping

HealthCare.gov may automatically renew your coverage, sometimes into a replacement plan if yours is unavailable. Review your renewal notice and application rather than assuming the plan and savings still fit.

Compare more than premiums. Check the deductible and out-of-pocket maximum, prescription coverage and whether your doctors remain in-network.

Make the change before Dec. 15

For HealthCare.gov, open enrollment runs Nov. 1, 2026, through Jan. 15, 2027. Select a plan by Dec. 15 for coverage starting Jan. 1, and pay the first premium by the insurer’s deadline. Some state Marketplaces have different dates.

Start with your household size and income estimate, then compare actual 2027 plans through your Marketplace. If the insurer’s bill doesn’t match your enrollment information, contact the insurer about the charge and the Marketplace about your eligibility or tax credit.

🧾 Found a billing mistake? Put the dispute in writing

An unfamiliar charge deserves a prompt call. But for a credit-card billing error, a phone conversation alone may not preserve your federal dispute rights. The deadline can arrive before the company finishes “looking into it.”

The clock starts with the statement

For qualifying credit-card billing errors, your written notice must reach the issuer within 60 calendar days after it sent the first statement showing the error.

Send it to the billing-inquiries address, which may differ from the payment address. Keep a copy and proof of delivery. Certified mail with a return receipt gives you a record of when it arrived.

Some issuers accept electronic billing-error notices as written notices. Check your card’s billing-rights instructions before relying on an app submission or email. Save the confirmation.

What the issuer must do

The issuer must acknowledge your written dispute within 30 days, unless it has already resolved it. It must finish the process within two complete billing cycles and no later than 90 days.

While it investigates, you can withhold the disputed amount and related charges. Keep paying the undisputed portion on time. The issuer cannot report you delinquent for properly withholding the disputed amount during that process.

Build a paper trail in three parts

  • The notice: Your name, address, account number, disputed amount and an explanation of what’s wrong.

  • The evidence: Copies of receipts, cancellation confirmations, contracts, emails and screenshots. Keep the originals.

  • The call log: Dates, representative names, reference numbers and promised next steps.

Be specific about the correction you want: remove a duplicate charge, apply a missing payment or refund a charge made after a documented cancellation.

Cancellation records matter, too. This guide to canceling car insurance explains why you should keep written confirmation, including for charges that appear after the cancellation date.

Debit cards have different rules

Report an unauthorized debit transaction immediately. If your card is lost or stolen, reporting within two business days after discovering the loss limits your liability to $50. Waiting longer can increase your exposure.

If you still have the card but someone used its number, report the unauthorized transaction within 60 days after the statement was sent to avoid liability for later unauthorized transfers.

Banks have 10 business days to investigate. If they need longer, they must provide provisional credit, subject to applicable conditions and exceptions. Follow any request to confirm your dispute in writing.

Take the underlying bill to the right company

A card dispute and a complaint about your insurance, phone or subscription bill are separate processes. A card reversal doesn’t necessarily cancel a contract or settle what you owe.

For insurance, ask the insurer to explain the charge and correct any inaccurate information. A price increase alone doesn’t prove an error. Know why car insurance rates rise and homeowners premiums increase. If the issue remains unresolved, your state insurance department may be able to help.

If your insurance problem involves a claim rather than a premium charge, watch this video, “Don’t File a Home Insurance Claim Before Watching This,” for an overview of the claims process:

For phone or internet billing problems, an FCC complaint can get the issue in front of the provider. When the FCC serves a billing or service complaint, the provider has up to 30 days to respond. For unresolved bank or card issues, consider a CFPB complaint.

A complaint doesn’t guarantee a refund. Clear records make it easier to explain the problem and challenge an inadequate response.

Start with your latest statements. If something looks wrong, document it today.

🦃 Thanksgiving week pays people who plan now

Thanksgiving is Nov. 26. Travelers need pet care, hosts need help and stores need extra hands. If you want holiday work, start checking openings and offering specific services now.

Check the job behind the hiring headline

Amazon says it’s hiring more than 300,000 people across seasonal, part-time and full-time operations roles this holiday season. Seasonal employees earn an average of $20 an hour; that’s an average, not a guaranteed starting rate.

UPS plans more than 100,000 seasonal hires. Target lists starting wages of $15 to $24 an hour, depending on role and location. Apply through official employer sites and ask about expected hours, training and how long the job lasts.

Consider delivery before the holiday

DoorDash’s analysis of 2024 orders found that Thanksgiving Eve was its biggest grocery-delivery day, with orders nearly 90% above a typical day. Long checkout lines and extra mileage can still cut into your earnings.

Before accepting deliveries, ask your insurer whether your policy covers that work and what gaps remain in any platform coverage. It pays to know which car insurance is right for delivery drivers.

Watch the pets and the kids

Rover lists Nov. 26 to 29 as its 2026 Thanksgiving peak-rate period. Sitters choose their rates, so compare local listings rather than assuming a standard holiday markup.

For babysitting, Care.com reports an average posted rate of $19.81 an hour nationally. Your rate will depend on location, experience, the number of children and the hours required. Agree on duties and payment before booking.

Bake for the neighbors, carefully

Check your state’s cottage-food rules before taking orders. Allowed foods, permits, labels and sales limits vary. Refrigerated desserts can be restricted: Montana, for example, excludes pumpkin and cream pies from its cottage-food category because they require refrigeration for safety.

Get paid for setup and cleanup

You don’t have to cook the meal to earn money. Offer to set tables, arrange chairs, wash dishes or clean the kitchen after guests leave. Taskrabbit lists party cleaning as a service, or you can start with neighbors.

Make the offer specific: “Two hours of kitchen cleanup Thursday night.” Agree on the tasks, price and who provides supplies before you arrive.

Turn one job into a second booking

Ask whether the client needs help putting up decorations that weekend. Offer to unpack ornaments, decorate a tree or arrange indoor displays. Taskrabbit also lists holiday decorating services.

Stick to work you can handle safely and price the extra job separately.

Check coverage before quoting

Ask an insurer whether the work you plan to do is covered, including any business-use exclusions or limits. Describe the actual service (delivery, pet care, baking or cleaning) rather than assuming one policy covers everything.

This small business insurance calculator can estimate costs. Confirm the coverage and exclusions with the insurer before buying.

Keep the tax rules straight

Employee wages and self-employment income are treated differently. If you work independently, net self-employment earnings of $400 or more trigger self-employment tax. The standard combined rate is 15.3%, applied to 92.35% of business profit, with limits and adjustments depending on your circumstances. Income tax may also apply.

For 2026, eligible workers may deduct up to $25,000 per return in qualified voluntary tips from federal taxable income. The deduction phases out above modified adjusted gross income of $150,000, or $300,000 for joint filers, and has other eligibility and reporting requirements. Base pay and mandatory service charges aren’t qualified tips. The deduction doesn’t eliminate payroll or self-employment tax.

Set aside money from each payout. If you need to make a fourth-quarter federal estimated payment, the regular deadline is Jan. 15, 2027. Some workers can cover the extra tax by increasing withholding from another job.

Count all the hours

Start with what the job pays. Subtract gas, parking, supplies and platform fees, then divide what’s left by all the time it takes, including travel, shopping and cleanup. Allow for taxes, too.

If the take-home pay is worth your time, book it. If it isn’t, keep looking.

🤖 Before AI shops for your gifts, check what it can see and spend

Holiday scams ranked second in our reader poll. AI shopping adds another reason to slow down: some tools can move beyond recommending a gift to placing the order.

In its Nov. 3 holiday-security guidance, Mastercard advises shoppers to check what information an AI agent can access, what purchases they’ve authorized and when the tool needs approval. That advice still applies even when the app is legitimate.

Check 4 details before connecting your account

  • Permission to buy: Does the tool make suggestions, fill a cart or place orders? Start with recommendations if you’re unsure.

  • Spending controls: Set limits where available. Check whether shipping and taxes count, whether substitutions are allowed and whether the permission expires.

  • Approval: Require confirmation before checkout when the tool offers that option. If it doesn’t, decide whether automatic purchasing is worth it.

  • Seller and return policy: Know which merchant is selling the item, its return deadline and who handles a missing delivery or refund.

These are settings to look for, not features every shopping assistant provides.

Amazon, for example, has offered an Alexa feature that lets users authorize a purchase when an eligible deal becomes available, using the account’s default payment method and delivery address. Permission given earlier can lead to an order later.

A bad purchase isn’t automatically fraud

If a tool buys something you don’t want, don’t assume the bank will treat it as a stolen-card transaction. The permission you gave, what happened and the applicable dispute rules all matter.

Try to cancel promptly or use the merchant’s return process. If the charge is incorrect or the item wasn’t delivered as agreed, contact your card issuer about a billing-error dispute. Explain the facts accurately and preserve the authorization, order details and messages.

For online purchases, a credit card offers more useful billing-dispute protections than a debit card. But it doesn’t guarantee a refund for buyer’s remorse.

Check the store yourself

An AI recommendation isn’t proof that a seller is trustworthy. Open the merchant’s site independently, check its contact and return information, and compare the total price before approving payment.

In Mastercard’s 2025 global survey, 72% of consumers said they shop on unfamiliar websites during the holidays, while only 41% said they’re more cautious online. Nearly half said they would ignore security warnings for a deep discount. Those findings describe shopping behavior, not a measured wave of AI-agent scams.

Turn off permissions when the job is done

After buying the gift, review connected accounts, saved payment methods and any outstanding automatic-purchase instructions. Remove access you no longer need.

Let the assistant save you time finding options. Keep control of the seller, the budget and the final purchase.

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Individual investors should act consistently as investors, not speculators.

— Benjamin Graham

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The MoneyGeek Team

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