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Sure includes a built-in AI assistant that understands your financial data. Ask questions in plain English and get instant insights about your spending, income, accounts, and investments.

What the AI Assistant Can Do

The assistant has access to your financial data and can:

Answer Questions

Ask about spending patterns, account balances, and financial trends

Analyze Transactions

Find specific transactions or calculate totals by category

Review Budgets

Check budget progress and identify overspending

Track Investments

Get portfolio summaries, holdings, and performance data

Starting a Chat

Create a New Chat

  1. Click AI Assistant in the navigation menu
  2. Click New Chat or start typing in the chat input
  3. Ask your question in plain English
  4. The assistant responds with data from your accounts

Example Questions

  • “How much did I spend on groceries last month?”
  • “What are my top 5 spending categories this year?”
  • “Show me all transactions over $500 in the last 3 months”
  • “How does my dining spending compare to last year?”
  • “How much income did I have in Q1?”
  • “What’s my average monthly income?”
  • “Show me all income from freelance work this year”
  • “How much did I earn from dividends?”
  • “What’s the balance of my Chase checking account?”
  • “Show me all my accounts and their balances”
  • “Which account has the most transactions?”
  • “What’s my total net worth?”
  • “Am I over budget on any categories?”
  • “How much budget do I have left for dining?”
  • “What’s my savings rate this month?”
  • “Compare my actual spending to my budget”
  • “What’s my total portfolio value?”
  • “Show me my top holdings”
  • “How much have I gained/lost on AAPL?”
  • “What’s my cost basis for Bitcoin?”

How It Works

Function Calling

The AI assistant uses function calling to access your data:
  1. You ask a question
  2. The AI determines what data it needs
  3. It calls internal functions to fetch:
    • Transactions from specific periods
    • Account balances and history
    • Investment holdings and performance
    • Budget allocations and spending
    • Income statement totals
  4. The AI analyzes the data and responds in natural language
Privacy: The AI runs queries against your Sure data in real-time. No financial data is permanently stored in the chat logs beyond what’s visible in the conversation.

Available Functions

The assistant can call these functions:
  • GetTransactions - Retrieve transactions by date, category, account, or amount
  • GetAccounts - List accounts with balances and details
  • GetHoldings - Fetch investment holdings and performance
  • GetBalanceSheet - Calculate net worth, assets, and liabilities
  • GetIncomeStatement - Summarize income and expenses by category
  • ImportBankStatement - Help you upload CSV bank statements (advanced)
  • SearchFamilyFiles - Find documents you’ve uploaded (if enabled)

AI Models

Sure supports multiple AI models:
  • GPT-4 - OpenAI’s most capable model (default)
  • GPT-4 Turbo - Faster responses with large context
  • GPT-3.5 - Faster and cheaper for simpler questions
Select a model when starting a new chat. The default is set in your organization settings.

Chat Features

Conversation History

The assistant remembers context within a chat: You: “How much did I spend on groceries last month?” AI: “You spent $487 on groceries in March 2024.” You: “What about February?” AI: “In February 2024, you spent 512ongroceries.Thats512 on groceries. That's 25 more than March.” The AI maintains context so you can ask follow-up questions without repeating details.

Multiple Chats

Organize conversations by topic:
  • Tax Planning - Questions about deductions and income
  • Budget Review - Monthly spending check-ins
  • Investment Analysis - Portfolio performance tracking
Create a new chat for each topic to keep conversations organized.

Editing Chats

Manage your chat history:
  • Rename Chat - Give it a descriptive title
  • Delete Chat - Remove old conversations
  • Retry Message - If the AI response is unclear, retry to get a different answer

Tips for Better Results

Be Specific

Vague

“How much did I spend?”

Specific

“How much did I spend on dining in February 2024?”
The more specific your question, the more accurate and useful the answer.

Use Date Ranges

Clearly state the time period:
  • “Last month” = The previous calendar month
  • “Last 30 days” = Rolling 30-day window from today
  • “This year” = January 1 to today
  • “Q1 2024” = January-March 2024

Reference Categories

Use your actual category names:
  • ✅ “Groceries” (if that’s your category name)
  • ❌ “Food shopping” (unless you named it that)

Account Names

Refer to accounts by their name in Sure:
  • ✅ “Chase Checking” (if that’s how you named it)
  • ❌ “My checking account” (too vague if you have multiple)

Follow-Up Questions

Ask clarifying follow-ups:
  1. “How much did I spend on dining last month?”
  2. “Break that down by merchant”
  3. “Which merchant was the most expensive?”
The AI uses previous answers to provide deeper insights.

Examples

Spending Analysis

Question: “What are my top 3 spending categories this year, and how much have I spent in each?” AI Response:
Based on your 2024 spending so far, your top 3 categories are:
  1. Groceries: $2,847 (128 transactions)
  2. Dining & Restaurants: $1,923 (87 transactions)
  3. Transportation: $1,456 (45 transactions)
These three categories account for 62% of your total spending this year.

Budget Check

Question: “Am I over budget on any categories this month?” AI Response:
You’re currently over budget in 2 categories for March 2024:
  • Dining & Restaurants: Spent 312,budgeted312, budgeted 200 (56% over)
  • Shopping: Spent 445,budgeted445, budgeted 300 (48% over)
Overall, you’re at 94% of your total monthly budget with 8 days remaining.

Investment Query

Question: “Show me my top 5 holdings and their performance” AI Response:
Here are your top 5 holdings by market value:
  1. VTSAX (Vanguard Total Stock Market): 24,350(+24,350 (+3,120 / +14.7%)
  2. AAPL (Apple): 8,940(+8,940 (+1,240 / +16.1%)
  3. BTC-USD (Bitcoin): 6,500(+6,500 (+2,100 / +47.7%)
  4. MSFT (Microsoft): 5,670(+5,670 (+890 / +18.6%)
  5. VXUS (Vanguard International Stock): 4,200(+4,200 (+340 / +8.8%)
Total portfolio value: 78,234with+78,234 with +9,821 in unrealized gains (+14.4%)

Net Worth Trend

Question: “How has my net worth changed over the last 6 months?” AI Response:
Your net worth has grown from 42,300(September2023)to42,300 (September 2023) to 51,800 (March 2024). That’s an increase of $9,500 (+22.5%) over 6 months. Monthly breakdown:
  • Sep: $42,300
  • Oct: 43,100(+43,100 (+800)
  • Nov: 45,200(+45,200 (+2,100)
  • Dec: 46,800(+46,800 (+1,600)
  • Jan: 48,500(+48,500 (+1,700)
  • Feb: 50,100(+50,100 (+1,600)
  • Mar: 51,800(+51,800 (+1,700)
Your net worth has increased every month, averaging +$1,583/month.

Limitations

What the AI Can’t Do

The AI assistant cannot:
  • Make changes to your data (transactions, budgets, accounts)
  • Execute transfers or payments
  • Access external websites or real-time market data
  • Provide tax or investment advice
  • Predict future market movements
The assistant is read-only - it analyzes your data but doesn’t modify anything.

Data Scope

The AI only has access to:
  • Data in your Sure account (transactions, accounts, budgets)
  • Historical data you’ve synced or entered
  • Current holdings and balances
It doesn’t have:
  • Real-time market prices (uses last synced prices)
  • Data from accounts not connected to Sure
  • External economic data or news

Privacy & Security

How Your Data Is Used

When you use the AI assistant:
  1. Your question is sent to the AI model (OpenAI GPT)
  2. The AI determines what Sure data to fetch
  3. Sure queries your database and returns results
  4. The AI analyzes and responds
  5. Your financial data is not stored by OpenAI - only the conversation history (questions and answers) is logged
Sure uses OpenAI’s zero data retention agreement for enterprise customers. Your financial data is not used to train AI models.

What’s Sent to OpenAI

  • Your questions (in natural language)
  • AI responses (summaries and insights)
  • Function names (e.g., “GetTransactions”)
  • Not sent: Raw transaction data, account numbers, or sensitive details
Only the results returned from Sure’s database (already summarized) are included in the AI context.

Disabling the AI Assistant

If you prefer not to use AI:
  1. Don’t navigate to the AI Assistant page
  2. The assistant only activates when you explicitly open a chat
  3. No data is sent to AI providers unless you start a conversation

Frequently Asked Questions

Yes. Sure uses OpenAI’s enterprise API with zero data retention. Your financial data is not stored or used for AI training. Only anonymized summaries are sent to the AI.
No. The AI is read-only. It can view and analyze your data but cannot create, edit, or delete transactions, accounts, or budgets.
The AI interprets questions based on context. If the answer is wrong:
  1. Rephrase your question more specifically
  2. Check that your data is up to date (run a sync)
  3. Use the “Retry” button to regenerate the response
No. The AI can summarize your financial data but is not qualified to give tax advice. Always consult a licensed tax professional for tax planning and filing.
Try rephrasing:
  • Be more specific about dates and categories
  • Break complex questions into smaller parts
  • Use the exact names of accounts and categories from your Sure setup
Chat export is not currently available. You can manually copy/paste responses or take screenshots for your records.

Future Capabilities

Upcoming AI features:
  • Proactive Insights - The AI suggests optimizations without you asking
  • Budget Recommendations - AI-powered budget adjustments based on spending patterns
  • Investment Advice (disclaimer-protected) - Portfolio rebalancing suggestions
  • Voice Input - Ask questions by speaking instead of typing
  • Chart Generation - AI creates custom charts based on your questions
Feature availability depends on your Sure plan. Check the pricing page for details.

Reports

View detailed financial reports and trends

Transactions

Browse and filter transactions manually

Budgets

Review budget progress and spending goals

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