Top 10 Questions to Ask a Seller Before Buying When Their Emails Sound AI-Generated

When an email sounds like it was written by a bot: how to vet the seller fast

Decision fatigue and distrust are real. You’ve found a product you want, but the seller’s messages read like they were spat out by an AI — short, generic, oddly formal, or full of weird phrasings. Should you buy? This guide gives you a practical checklist: the top 10 questions to ask plus red flags and verification steps that restore purchase confidence and protect your wallet in 2026.

Why this matters now (2026 context)

By late 2025 and into 2026, email and inbox platforms like Gmail rolled out advanced AI features (built on models like Google’s Gemini 3) that change how users read and manage messages. These tools also increased the volume of AI-generated communications and introduced "AI overviews" that summarize messages for busy users. At the same time, marketers and scammers alike leaned into automated copy — producing what industry commentators called "AI slop" (a 2025 buzzword for low-quality AI output). The result: buyers see more cookie-cutter seller replies and struggle to separate legitimate operations from shady ones.

Immediate priorities — the inverted pyramid

Start with the essentials: protect payment, confirm the product’s authenticity, and secure a clear return path. Then verify the seller’s credibility through details only a legitimate operation can provide. Use the 10 questions below as your working script when emails feel robotic.

Top 10 questions to ask a seller whose emails sound AI-generated

1. “Can you send a timestamped, unedited live photo or short video of the exact item I’d receive?”

   Why ask it: AI templates often recycle product photos and stock images. A live photo or video (timestamped or clearly showing a recent date) proves the item exists and is in the described condition. Ask for a short clip of the product next to a current newspaper or device with a visible date/time.

   Red flag: Seller refuses or delays without a good reason. Excuses like "our staff is busy" or "we don't usually do that" are suspicious.

2. “What’s your business registration / marketplace store page / physical address I can verify?”

   Why ask it: Legitimate sellers supply verifiable business details. A domain with an address, a public company registration number, or a filled-out marketplace storefront boosts trust.

   How to verify: Cross-check business numbers on government sites, view the physical address on Google Maps, and inspect the seller’s marketplace history and feedback.

3. “Can you provide an item serial number, SKU, or factory barcode?”

   Why ask it: Authentic products usually show traceable identifiers. With serials or barcodes you can contact the manufacturer or check authenticity databases.

   Actionable step: If given a serial, ask the manufacturer if the number is valid and whether the item was sold through authorized channels.

4. “What exact warranty and return policy applies to this purchase, in writing?”

   Why ask it: AI-generated replies often paraphrase generic policies. Request a verbatim policy statement that includes timelines, costs for returns, and who pays shipping. Make sure it aligns with marketplace protections or your card issuer’s chargeback window.

   Red flag: Vague timelines ("return allowed" without details) or copying from a different brand’s policy.

5. “Which payment methods do you accept? Can I use a payment method with buyer protection?”

   Why ask it: Your safest options are payment channels with buyer protection (credit cards, PayPal with Goods/Services, major marketplace escrow). Avoid direct bank transfers, cryptocurrency, or apps without dispute resolution.

   Actionable language to use: “I’ll pay with [credit card/PayPal]. Do you provide an invoice with my name and item details?” If they pressure you to use an unsupported method, walk away.

6. “Can you confirm the estimated shipping method, carrier, tracking number, and expected delivery window?”

   Why ask it: AI replies may promise shipping without real logistics. A valid tracking number from a major carrier or marketplace shipping system shows the seller processed your order.

   How to verify: Enter the tracking number on the carrier’s website. If tracking doesn’t update in 48–72 hours after shipping confirmation, contact the carrier and your marketplace.

7. “Who handled my order—human agent or automated system? May I speak to a named representative?”

   Why ask it: Sellers that over-rely on AI sometimes hide the lack of human oversight. A named contact, even if remote, indicates accountability. Ask for a short live chat or phone call if the purchase is high-value.

   Red flag: Persistent refusal to allow a brief live call or to identify any human contact.

8. “Can you share recent (dated) customer photos or public reviews for this SKU?”

   Why ask it: Authentic sellers can point to verifiable user-generated content. Photos posted on social platforms, marketplace reviews, or video unboxings that match the item reduce risk.

   How to verify: Cross-check review screenshots on the original platform and look for reviewer profiles with a purchase history.

9. “Please send a detailed invoice that includes item specifics, total cost (taxes, shipping), and seller contact information.”

   Why ask it: A legitimate invoice is a legal document that protects buyers. It’s also necessary if you file a dispute with a payment provider.

   Actionable tip: Keep the invoice and all emails; they’re evidence if you need chargebacks or claims.

10. “If I receive something different from what’s described, what’s the exact dispute and refund process?”

    Why ask it: Understand timelines for returns, restocking fees, and how refunds are issued. This helps you set expectations and reduces surprises.

    Pro tip: Ask for the text of the policy and key deadlines (e.g., “returns accepted within 14 days of delivery for a full refund”).

Red flags that an AI-sounding email hides a risky seller

• Generic salutations ("Hello Customer" with no name) repeated across messages.
• Overly polished but vague copy that avoids concrete details about the item or process.
• Pressure tactics — "limited stock" or "offer expires now" without verifiable countdowns.
• Requests for risky payments (wire transfer, crypto, gift cards).
• Mismatch in sender info — email domain differs from the business website (e.g., Gmail/Hotmail for companies claiming to be official).
• Inconsistent product images across messages or stock imagery that matches many sellers.
• No willingness for minor human verification — refusal to video-call or provide a serial number.

“AI helps sellers scale, but hands-off automation lowers buyer trust. Ask for proof.” — Trusted buyer-advisor tip

How to ask these questions without sounding confrontational

Use friendly, exact phrasing. If an email sounds AI-generated, assume the seller is scaling communications rather than scamming. A calm, specific approach usually gets results.

• Start with appreciation: “Thanks — looks great. Quick confirmation before I buy…”
• Ask one question at a time. Multiple requests can trigger automated responses.
• Offer a reason for each request: “I need a timestamped photo to confirm condition for my records.”

Sample scripts you can paste and send

Use these on marketplaces, in emails, or chat windows.

Low-friction (small purchases)

“Thanks — could you send a quick photo of the exact item with today’s date visible (e.g., next to my phone screen)? Also, please confirm payment methods that include buyer protection.”

High-value or used items

“Before I place a payment, please provide (1) a short video showing the item and serial number, (2) a written warranty/return policy, and (3) the tracking method you’ll use. I prefer to pay via credit card or PayPal for protection.”

Verification checklist (step-by-step after you ask the questions)

1. Receive seller’s answers and files — save everything.
2. Verify photos/videos for timestamps and matching serials.
3. Check tracking and carrier details once shipped.
4. Confirm invoice contains seller contact and payment details.
5. If doubts remain, contact the marketplace or your payment provider before releasing funds.

What to do if the seller fails verification

If you detect issues — inconsistent details, refusal to provide proof, or pressure to use risky payment methods — stop. Cancel the order if possible and escalate:

• Report the listing to the marketplace or platform.
• Open a dispute with your payment provider (credit card company, PayPal) and provide your saved emails and invoices.
• File a complaint with consumer protection agencies if the loss is significant.

Advanced strategies for power shoppers (2026 tips)

Use these when shopping frequently or on channels with heavy AI messaging.

• Reverse-image search: Photos used across multiple seller accounts suggest stock images. Use Google Images or TinEye.
• Check CRM footprints: Sellers using reputable CRMs (e.g., HubSpot, Salesforce) often include consistent metadata in automated emails. Ask for order IDs or links tied to their CRM dashboard.
• Cross-platform reputation: Search for seller names, phone numbers, and email domains on forums, Reddit, and consumer complaint sites in 2025–2026 threads.
• Use escrow for big purchases: Third-party escrow services add a neutral layer for expensive items.

Real-world mini case: How I avoided a $900 loss

In late 2025, a reader reached out: they found a high-end camera at a deep discount. The seller’s emails were short, generic, and pushed immediate payment via bank transfer. The buyer used my checklist: asked for a timestamped video and serial number, verified the serial with the manufacturer (it was invalid), and canceled. The seller disappeared. The buyer saved $900 and reported the listing. This is an example of how a few targeted questions prevent big losses.

Why some sellers sound AI-generated — legitimate reasons

Not all robot-sounding emails mean fraud. Small businesses and busy sellers increasingly use AI tools to scale responses, especially after Gmail’s 2025–2026 AI inbox shifts. But responsible sellers pair automation with human review and can provide the verifications above. The difference is transparency and willingness to prove claims when asked.

Final takeaway: Ask, verify, then pay

When a seller’s messages sound AI-generated, treat the conversation like a verification process rather than a negotiation. Ask the 10 targeted questions, watch for the red flags, and always prioritize buyer-protected payment methods. Those steps cut risk sharply and let you shop with confidence in 2026’s AI-rich inbox environment.

Next steps — quick cheat-sheet

• Before paying: request live photo/video + serial/SKU.
• Prefer protected payments (credit card, PayPal Goods/Services, marketplace escrow).
• Get a written invoice and explicit return/warranty terms.
• Verify tracking and keep all correspondence.

Call to action

If you encounter a seller whose replies feel robotic, use this checklist right away and save the responses. Want a printable checklist or ready-to-send scripts for different purchase sizes? Click through to download our free Seller Vetting Checklist and template messages — or ask us for a tailored script for a specific product and we’ll draft it for you.

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