With AI, you can have your assistant keep an eye on your money for you — just tell it, in plain language, what matters to you and when to speak up.
Claude and ChatGPT both support scheduled tasks — prompts that run on a cadence you pick and message you with the result. Pair that with your Wise Penny connector (Claude / ChatGPT) and you have a small, personal financial watchdog that only pings when there's something worth your attention.
Pick one or two to start. Each prompt is a complete scheduled task — copy it, paste it into Claude or ChatGPT, and set the cadence shown. The dollar amounts, percentages, and category lists are defaults to make the prompts concrete — edit them to match your accounts, your lifestyle, and what you actually want to hear about.
A category-level read on the week, with extra attention to discretionary categories where spending tends to drift quietly.
Summarize my spending over the last 7 days. Show me: - the top 10 spending categories this week with $ totals - for each, the change vs. the trailing 3-week average for that category (as $ and %) - a separate callout on discretionary categories — restaurants, coffee, shopping, entertainment, travel, rideshare, delivery — flagging any that ran more than 25% above their trailing 3-week average Lead with a one-sentence headline about the week. If everything is in line with my normal, keep the rest brief.
Recurring charges drift quietly — new subscriptions sneak in, prices creep up, old ones stop showing up. This catches the changes without spamming you about the steady ones.
Look at my recurring charges over the last 30 days vs. the prior 30 days. Flag anything that: - appeared for the first time this period - stopped appearing (may be cancelled, paused, or moved to a different card) - increased by more than 10% or $5 - posted twice in a single month when it normally posts once - hit a card or account different from where it usually hits For each, give the merchant, amount, account, and what changed. If nothing changed, just say so.
A high-level read on how the month landed — income, spending, savings, and any categories that genuinely deviated from your recent pattern.
Summarize last month's finances at a high level: 1. total income 2. total spending 3. net savings (income minus spending) 4. how savings compares to the trailing 3-month average — up, down, or flat, with the $ amount of the change Then list any spending categories that were more than 25% or $200 different from their trailing 3-month average, and briefly explain what drove the change if you can tell from the transactions. Don't enumerate routine categories — only flag what actually moved.
Only hear from your assistant when a depository account dips below a floor you care about, or a credit card balance crosses a ceiling.
Check the current balances on all my accounts. Flag anything that crosses these thresholds: - any checking or savings account with a balance below $1,000 - any credit card with a current balance above $2,000 For each, give the account name, the current balance, and how far past the threshold it is. If nothing is crossed, just reply "all balances within thresholds."
Claude's scheduled tasks live in the Claude desktop app. They run on your machine, so your computer needs to be awake when the task is scheduled to fire (there's a Keep awake toggle on the Scheduled page if you want Claude to prevent sleep). Make sure your Wise Penny connector is set up inside the desktop app — same flow as the Connect Claude guide, just from the desktop app's settings.
In the Claude desktop app sidebar, switch to Cowork and select Scheduled. Click New task in the top right to open the create dialog.
Shortcut: inside any existing chat or task, type /schedule to jump straight into scheduling.

Click Save. Your task appears in the Scheduled list and runs at the next scheduled time — Claude opens a new chat, queries Wise Penny, and surfaces the result. You can pause, edit, or delete the task from that list any time.

In ChatGPT there's no separate scheduling menu — you just ask. Open chatgpt.com, start a new chat with the Wise Pennyconnector enabled, paste one of the prompts above (or describe what you want in your own words), and once you're happy with the reply, follow up with something like:
ChatGPT creates a recurring task and confirms the cadence. The example below shows scheduling a weekly eating-out-vs-groceries chart — the same flow works for any of the prompts above. Tasks require a Plus, Pro, or Team plan, and you can review, pause, edit, or delete them later under Settings → Tasks.
