PROMPT This AI Challenge

"The Prompt This Rapid Fire Smackdown"  

Every episode of the PROMPT This podcast includes an AI Challenge for the audience.  Follow the instructions below to complete this episode's challenge.

Automate Your Inbox to Recover Missed Amazon Savings 

What if your inbox did more than store receipts? What if it actively worked to recover money you already spent?

This PROMPT This AI Challenge turns a common annoyance, price drops after purchase, into a practical automation experiment. You will train AI to scan your inbox for Amazon orders, identify recent purchases, check for price changes, and draft refund requests with minimal human effort.

This is a confidence-building challenge designed to show how AI can automate repetitive, low-value work while delivering tangible financial returns.

Why This Challenge Matters

Real-world payoff 

Price adjustments happen constantly across consumer goods, software subscriptions, travel, and B2B services. Most refunds go unclaimed simply because no one tracks them.

Operational confidence 

This challenge demonstrates how AI can orchestrate multi-step workflows across unstructured data like emails and receipts.

Practical fun 

You are effectively converting your inbox from a passive archive into an active financial assistant.

Manufacturers, service providers, and product companies all deal with pricing changes. This challenge mirrors the same logic used in revenue assurance and contract compliance, applied at a personal scale.

 Step 1: Turn on the Gmail Connector in ChatGPT

NOTE: This AI Challenge requires a paid-for version of ChatGPT.  The free version does not include the Gmail connector.

1. Navigate to ChatGPT Settings
2. Click on Apps & connectors
3. Click on Gmail
   
4. Click on the Connect button to start the process of connecting your Gmail inbox into your ChatGPT.
   

Step 2: Set AI Loose

Start with a clear, structured instruction set for your AI assistant:

• Review my Gmail inbox for Amazon orders from the last 90 days

• Extract item name, website, purchase date, vendor, purchase price and billing cadence

• Check the vendor website or major retailers for a lower price than what I paid for these Amazon orders

Step 3: Return and Reorder If Lower Prices Available

If ChatGPT finds a lower price for the same item, you can simply return your Amazon purchase and order the lower-priced item.  Simple as that!

AI Prompts

• Scan my inbox for purchase receipts from the last 90 days and extract key purchase details

• Check current prices for each extracted item on vendor websites

• Identify purchases with lower current prices and calculate refund differences

• Draft a professional refund request email for each qualifying purchase

• Create a weekly savings report summarizing potential refunds
  
  

Final Thought

The Amazon Deal Hunter is not about saving a few dollars. It is about proving a larger point. AI excels at repetitive, rules-based work that humans consistently neglect. By automating your inbox, you are practicing the same mindset shift businesses must make to stay competitive. Whether the outcome is five dollars or five hundred, the real value is learning how to turn AI into an active operator rather than a passive tool.