Below is a two-step approach for each of the 7 categories you specified:

• List 10 candidate questions for each relevant data connector type within that category.
• Select the “Top 8” questions (across all data connectors in that category) that best satisfy your 3 guiding principles:
• (1) Useful personalization toward transactions/recommendations
• (2) Impress the user with deep, factual knowledge
• (3) Easy for an automated TEE grader to verify using raw JSON data

1. SOCIAL

Data Connector Types

• Twitter (basic info from OAuth)
• Discord (username, servers, login times)
• Telegram (username, auth date)
• Facebook/Instagram (inferred via Gmail receipts or direct OAuth)

A. Candidate Questions (10 Each)

Twitter (10)

• Do we know the user’s Twitter handle or username?
• How many Twitter followers does the user have?
• How many accounts does the user follow on Twitter?
• What is the date/time of the user’s last tweet?
• How many tweets has the user posted in the last 7 days?
• How many direct messages did the user receive on Twitter in the last 7 days?
• What is the user’s Twitter ID from OAuth?
• On what date did the user join Twitter?
• How many pinned or bookmarked tweets does the user have?
• How many Twitter login/security notifications are in Gmail?

Discord (10)

• What is the user’s Discord handle or user ID?
• How many Discord servers has the user joined in total?
• What is the name of the most recent Discord server the user joined?
• What is the date/time of the user’s last Discord login?
• How many direct messages has the user received on Discord in the last 7 days?
• How many roles does the user have in their largest Discord server?
• On what date did the user create their Discord account?
• How many hours has the user spent in voice channels in the last 30 days?
• How many new Discord servers has the user joined in the last 30 days?
• Do any recent Discord password reset or security emails appear in Gmail?

Telegram (10)

• What is the user’s Telegram username?
• On what date did the user last log in to Telegram?
• How many Telegram channels or groups has the user joined?
• How many Telegram messages has the user sent in the last 7 days?
• When did the user originally create their Telegram account?
• Has the user’s Telegram phone number been verified?
• How many new Telegram contacts has the user added in the last 30 days?
• Are there any Telegram security or login alert emails in Gmail?
• How many pinned chats does the user have on Telegram?
• Is two-step verification enabled on the user’s Telegram account?

Facebook/Instagram (10)

• Does the user have an active Facebook or Instagram account (based on receipts or OAuth)?
• How many login or security notifications from Facebook/Instagram appeared in Gmail in the last 30 days?
• How many friend/follow requests did the user receive in the last 7 days?
• When did the user create their Facebook or Instagram account?
• How many event invites from Facebook did the user receive in the last 30 days?
• How many groups or pages has the user joined on Facebook in total?
• How many promotional or ad-related emails from Facebook/Instagram are in Gmail in the last 30 days?
• Are there any password reset or suspicious login alerts from Facebook/Instagram in the last 90 days?
• How many direct message notifications from Instagram does Gmail show in the last 7 days?
• How many watch party or live video notifications are in the user’s Gmail?

B. Top 8 Questions (Covering All Social Connectors)

• Do we know the user’s Twitter handle or username?
• How many Discord servers has the user joined in total?
• What is the user’s Telegram username?
• Does the user have an active Facebook or Instagram account (based on receipts or OAuth)?
• How many direct messages did the user receive on Twitter in the last 7 days?
• How many friend/follow requests did the user receive on Facebook/Instagram in the last 7 days?
• What is the date/time of the user’s last Discord login?
• How many login or security notifications from Facebook/Instagram appeared in Gmail in the last 30 days?

2. PRODUCTIVITY

Data Connector Types

• Gmail
• Google Calendar

A. Candidate Questions (10 Each)

Gmail (10)

• How many emails did the user receive in the last 7 days?
• How many emails did the user send in the last 7 days?
• How many unread emails older than 7 days remain?
• Who is the most frequent sender in the last 30 days?
• How many pinned or starred emails exist in the last 30 days?
• How many spam emails were received in the last 30 days?
• How many new labels or filters were created in the last 30 days?
• How many email threads have more than 5 messages in the last 30 days?
• When is the date of the earliest email found in the mailbox?
• How many password reset or security alert emails are in the last 30 days?

Google Calendar (10)

• How many calendar events occurred in the last 7 days?
• How many upcoming events are scheduled in the next 7 days?
• What is the earliest event date found in the calendar?
• How many recurring events does the user have in the next 30 days?
• How many event invites did the user accept in the last 30 days?
• How many events did the user decline in the last 30 days?
• Which time block (morning/afternoon/evening/night) has the most events in the last 30 days?
• How many meeting invites from external domains are on the user’s calendar in the last 30 days?
• How many canceled events are on the user’s calendar in the last 30 days?
• When is the next upcoming event (date and time)?

B. Top 8 Questions (Covering Both Connectors)

• How many emails did the user receive in the last 7 days?
• How many emails did the user send in the last 7 days?
• How many calendar events occurred in the last 7 days?
• How many upcoming events are scheduled in the next 7 days?
• How many spam emails were received in the last 30 days?
• Which time block has the most calendar events in the last 30 days?
• How many pinned or starred emails exist in the last 30 days?
• When is the next upcoming event (date and time)?

3. DAILY LIFE

Data Connector Types (via Gmail receipts)

• Ride (Uber, Lyft, Waymo, Didi, Grab)
• Food Delivery (Uber Eats, DoorDash, Grubhub)
• Fresh Delivery (Instacart, Amazon Fresh, Costco, etc.)

A. Candidate Questions (10 Each)

Ride Services (10)

• How many Uber ride receipts are found in the last 30 days?
• How many Lyft ride receipts are found in the last 30 days?
• Which rideshare app is used most frequently in the last 90 days?
• When was the user’s last Uber ride (date)?
• How many airport rides has the user taken in the last 90 days?
• What is the earliest date of any rideshare receipt in Gmail?
• Approximately how much has the user spent on rideshare in the last 30 days?
• How many canceled ride receipts are in the last 30 days?
• Which was the last rideshare service used (app name)?
• How many other rideshare services (Waymo, Didi, Grab) receipts are found in the last 90 days?

Food Delivery (10)

• How many Uber Eats receipts are found in the last 30 days?
• How many DoorDash receipts are found in the last 30 days?
• Which food delivery app is used most frequently in the last 90 days?
• How much has the user spent on food delivery in the last 30 days?
• What is the date of the user’s most recent food delivery order?
• How many different restaurants has the user ordered from in the last 30 days?
• How many refunds or canceled food orders occurred in the last 30 days?
• What is the earliest date of any food delivery receipt?
• How many promotional or discount codes has the user redeemed for food delivery in the last 30 days?
• On which date did the user spend the most on a single food delivery order in the last 30 days?

Fresh Delivery (10)

• How many Instacart receipts are found in the last 30 days?
• How many Amazon Fresh receipts are found in the last 30 days?
• How many Costco same-day delivery receipts are found in the last 30 days?
• What is the earliest date of a fresh grocery delivery receipt?
• Which fresh delivery service is used most frequently in the last 90 days?
• How many times has the user purchased fresh produce in the last 30 days?
• How much has the user spent on fresh grocery delivery in the last 30 days?
• When was the user’s most recent fresh delivery date?
• How many canceled fresh delivery orders occurred in the last 30 days?
• How many scheduled deliveries vs. on-demand deliveries has the user used?

B. Top 8 Questions (Covering All Daily Life Connectors)

• How many Uber ride receipts are found in the last 30 days?
• Which rideshare app is used most frequently in the last 90 days?
• How many Uber Eats receipts are found in the last 30 days?
• Which food delivery app is used most frequently in the last 90 days?
• How many Instacart receipts are found in the last 30 days?
• Which fresh delivery service is used most frequently in the last 90 days?
• Approximate total spent on daily life services (ride + food + fresh) in the last 30 days?
• Date of the most recent daily life service usage (any ride or delivery)?

4. SHOPPING

Data Connector Types (via Gmail receipts)

• Amazon
• Shopify-based stores (any store using Shopify)
• Other Retailers (Shein, Macy’s, Lululemon, etc.)

A. Candidate Questions (10 Each)

Amazon (10)

• How many Amazon order confirmation emails are in the last 30 days?
• Approximately how much has the user spent on Amazon in the last 30 days?
• How many Amazon returns or refunds were processed in the last 90 days?
• How many times did the user use Amazon Prime shipping in the last 30 days?
• What is the earliest Amazon purchase date found in Gmail?
• When was the most recent Amazon purchase?
• How many “Subscribe & Save” confirmations are in the last 90 days?
• How many digital product purchases (e.g., Kindle e-books) are in the last 30 days?
• Which product category appears most often in Amazon orders in the last 90 days?
• How many Amazon Fresh grocery orders are found in the last 30 days?

Shopify (10)

• How many receipts from Shopify-based stores are in the last 30 days?
• Approximately how much has the user spent on Shopify-based purchases in the last 30 days?
• How many refunds from Shopify-based stores were processed in the last 90 days?
• What is the earliest Shopify-based purchase date?
• When was the most recent Shopify-based purchase?
• How many different Shopify-based stores has the user purchased from in the last 90 days?
• Which single Shopify-based store did the user purchase from most frequently in the last 90 days?
• How many discount or coupon codes were used for Shopify in the last 30 days?
• How many outstanding shipments are awaiting delivery from Shopify-based orders?
• What is the earliest shipping date among Shopify orders in the last 30 days?

Other Retailers (10)

• How many Shein order confirmations are in the last 30 days?
• How many Macy’s order confirmations are in the last 30 days?
• How many Lululemon order confirmations are in the last 30 days?
• Which retailer (Shein, Macy’s, Lululemon, etc.) is most frequently used in the last 90 days?
• How much has the user spent across these “other retailers” in the last 30 days?
• When was the user’s most recent purchase from any of these other retailers?
• How many returns or exchanges are found in the last 30 days for these retailers?
• What is the earliest purchase date from these other retailers?
• How many promotional or discount codes did the user use with these other retailers in the last 30 days?
• How many shipping delay or re-shipment notices appear in the last 30 days?

B. Top 8 Questions (Covering All Shopping Connectors)

• How many Amazon order confirmation emails are in the last 30 days?
• Approximately how much has the user spent on Amazon in the last 30 days?
• How many receipts from Shopify-based stores are in the last 30 days?
• How many order confirmations from Shein or other retailers are in the last 30 days?
• Which store/retailer appears most frequently in the last 90 days (Amazon, Shopify-based, or other)?
• When was the most recent purchase from any retailer (Amazon/Shopify/Other)?
• Approximately how much has the user spent across all retailers in the last 30 days?
• How many refunds or returns are found from all retailers in the last 90 days?

5. WEB3

Data Connector Types

• Crypto Wallet Apps (MetaMask, Phantom, WalletConnect)
• (Additional on-chain transaction data from 3rd-party search APIs if connected)

A. Candidate Questions (10)

• Does the user have a MetaMask wallet address connected?
• How many distinct wallet addresses does the user have connected?
• What is the most recent transaction date on the user’s Ethereum wallet?
• What is the highest-value transaction found in the last 30 days?
• How many NFTs does the user own across all connected wallets?
• How many DeFi protocol interactions has the user made in the last 90 days?
• Does the user have a Phantom wallet for Solana?
• How many inbound token transactions occurred in the last 30 days?
• How many outbound token transactions occurred in the last 30 days?
• Does the user hold any stablecoins (e.g., USDT, USDC) in the last known wallet state?

B. Top 8 Questions (Web3)

• Does the user have a MetaMask wallet address connected?
• How many distinct wallet addresses does the user have connected?
• What is the most recent transaction date on the user’s Ethereum wallet?
• How many NFTs does the user own across all connected wallets?
• How many DeFi protocol interactions has the user made in the last 90 days?
• How many inbound token transactions occurred in the last 30 days?
• How many outbound token transactions occurred in the last 30 days?
• Does the user hold any stablecoins in the last known wallet state?

6. FINANCE

Data Connector Types (via Gmail receipts)

• Stock Broker (Robinhood, IB, Futu, Tiger, Charles Schwab, etc.)
• Crypto CEX (Coinbase, Binance, Kraken, OKX, Bybit, etc.)

A. Candidate Questions (10 Each)

Stock Broker (10)

• How many trade confirmation emails from stock brokers are in the last 30 days?
• How many deposit or withdrawal confirmations from brokers are in the last 30 days?
• What is the earliest trade confirmation date found in Gmail?
• What is the most recent trade confirmation date?
• How many margin call or margin interest emails are present?
• How many dividend notifications are in the last 90 days?
• Does the broker send monthly or quarterly statements, and how many are in the last 12 months?
• How many new account or service upgrade emails have appeared in the last 90 days?
• How many position or holdings summary emails are there?
• How many promotional or marketing emails from brokers have arrived in the last 30 days?

Crypto CEX (10)

• How many deposit confirmations from crypto exchanges are in the last 30 days?
• How many withdrawal confirmations from crypto exchanges are in the last 30 days?
• How many trade or order execution emails from crypto exchanges are in the last 30 days?
• What is the earliest transaction date from any crypto exchange found in Gmail?
• What is the most recent transaction date from any crypto exchange?
• How many 2FA or security alert emails from crypto exchanges have appeared in the last 90 days?
• How many KYC or verification emails from crypto exchanges are found?
• How many promotional or new listing emails from crypto exchanges are in the last 30 days?
• Does the user have an advanced trading or margin account based on exchange statements?
• How many stablecoin trades or deposits are noted in the last 30 days?

B. Top 8 Questions (Covering Both Finance Connectors)

• How many trade confirmation emails from stock brokers are in the last 30 days?
• How many deposit confirmations from crypto exchanges are in the last 30 days?
• How many withdrawal confirmations from crypto exchanges are in the last 30 days?
• What is the most recent trade confirmation date (stock or crypto)?
• How many margin call or margin interest emails from brokers exist?
• How many 2FA or security alert emails from crypto exchanges have appeared in the last 90 days?
• Does the user have an advanced trading or margin account with any crypto exchange?
• How many dividend notifications (stock) or stablecoin reward emails (crypto) exist in the last 90 days?

7. AI (AI-Native Chat History / Subscriptions)

Data Connector Types

• Gmail receipts or subscription emails from ChatGPT, Bard/Gemini, DeepSeek, Perplexity, Character AI, etc.

A. Candidate Questions (10)

• How many ChatGPT subscription or usage emails are in the last 30 days?
• How many Bard/Gemini usage or subscription emails are in the last 30 days?
• How many DeepSeek usage summary or update emails are in the last 30 days?
• When did the user first subscribe to any AI service (based on earliest subscription email)?
• How many AI service subscription renewals have occurred in the last 12 months?
• How many paid AI service receipts (e.g. ChatGPT Plus) appear in the last 90 days?
• How many support or help ticket emails with AI tools appear in the last 90 days?
• Does the user have an enterprise or pro plan with any AI service?
• How many times has the user received an AI-scheduling or auto-generated calendar invitation in the last 30 days?
• Did the user sign up for any new AI service trial in the last 90 days?

B. Top 8 Questions (AI)

• How many ChatGPT subscription or usage emails are in the last 30 days?
• How many Bard/Gemini usage or subscription emails are in the last 30 days?
• When did the user first subscribe to any AI service (based on earliest subscription email)?
• How many AI service subscription renewals have occurred in the last 12 months?
• How many paid AI service receipts appear in the last 90 days?
• How many support or help ticket emails with AI tools appear in the last 90 days?
• Does the user have an enterprise or pro plan with any AI service?
• How many AI-scheduling or auto-generated calendar invites have been sent in the last 30 days?

Final Summary of “Top 8” Questions per Category

Below is the condensed list of the 8 best questions for each category, which collectively cover all data connector types within that category and adhere to your 3 key guidelines.

SOCIAL (8)

• Do we know the user’s Twitter handle or username?
• How many Discord servers has the user joined in total?
• What is the user’s Telegram username?
• Does the user have an active Facebook or Instagram account?
• How many direct messages did the user receive on Twitter in the last 7 days?
• How many friend/follow requests on Facebook/Instagram in the last 7 days?
• What is the date/time of the user’s last Discord login?
• How many login/security notifications from Facebook/Instagram in Gmail in the last 30 days?

PRODUCTIVITY (8)

• How many emails did the user receive in the last 7 days?
• How many emails did the user send in the last 7 days?
• How many calendar events occurred in the last 7 days?
• How many upcoming events are scheduled in the next 7 days?
• How many spam emails were received in the last 30 days?
• Which time block has the most calendar events in the last 30 days?
• How many pinned or starred emails exist in the last 30 days?
• When is the next upcoming event (date/time)?

DAILY LIFE (8)

• How many Uber ride receipts are found in the last 30 days?
• Which rideshare app is used most frequently in the last 90 days?
• How many Uber Eats receipts are found in the last 30 days?
• Which food delivery app is used most frequently in the last 90 days?
• How many Instacart receipts are found in the last 30 days?
• Which fresh delivery service is used most frequently in the last 90 days?
• Approximate total spent on daily life services (ride + food + fresh) in the last 30 days?
• Date of the most recent daily life service usage (any ride or delivery)?

SHOPPING (8)

• How many Amazon order confirmations in the last 30 days?
• Approximately how much has the user spent on Amazon in the last 30 days?
• How many Shopify-based store receipts in the last 30 days?
• How many Shein or other retailer order confirmations in the last 30 days?
• Which store or retailer appears most frequently in the last 90 days?
• When was the most recent purchase from any retailer?
• Approximately how much has the user spent across all retailers in the last 30 days?
• How many refunds or returns from all retailers in the last 90 days?

WEB3 (8)

• Does the user have a MetaMask wallet address connected?
• How many distinct wallet addresses does the user have connected?
• What is the most recent transaction date on the user’s Ethereum wallet?
• How many NFTs does the user own across all connected wallets?
• How many DeFi protocol interactions in the last 90 days?
• How many inbound token transactions in the last 30 days?
• How many outbound token transactions in the last 30 days?
• Does the user hold any stablecoins in the last known wallet state?

FINANCE (8)

• How many trade confirmation emails from stock brokers in the last 30 days?
• How many deposit confirmations from crypto exchanges in the last 30 days?
• How many withdrawal confirmations from crypto exchanges in the last 30 days?
• What is the most recent trade confirmation date (stock or crypto)?
• How many margin call or margin interest emails from brokers exist?
• How many 2FA or security alert emails from crypto exchanges in the last 90 days?
• Does the user have an advanced trading or margin account with any crypto exchange?
• How many dividend notifications (stock) or stablecoin reward emails (crypto) in the last 90 days?

AI (8)

• How many ChatGPT subscription or usage emails in the last 30 days?
• How many Bard/Gemini usage or subscription emails in the last 30 days?
• When did the user first subscribe to any AI service (based on earliest email)?
• How many AI service subscription renewals in the last 12 months?
• How many paid AI service receipts appear in the last 90 days?
• How many help/support ticket emails with AI tools in the last 90 days?
• Does the user have an enterprise or pro plan with any AI service?
• How many AI-scheduling or auto-generated calendar invites in the last 30 days?

Why These 8 Are “Best”

• (1) Useful for transactional predictions or recommendations
  E.g., “Does the user have an upcoming birthday event on the calendar?” or “Which store do they shop at most frequently?” leads to relevant suggestions.
• (2) Impressive knowledge
  The user sees these questions and recognizes the AI can glean meaningful, aggregated insights from raw JSON or streaming data (e.g., the user’s last rideshare usage date).
• (3) Easy for a TEE grader to verify
  Each question can be answered via straightforward search or count operations (e.g., counting receipts, matching wallet addresses, scanning for event invites) on the user’s JSON data. By covering distinct connectors within each category, these top 8 questions give a broad, high-value snapshot of the user’s personal data—satisfying your overall personalization goals.