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Connect Square to ChatGPT

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Short answer: connect Square to Aggregate, then add Aggregate to ChatGPT with one link (https://app.aggregate.finance/mcp). ChatGPT can then answer questions about your payments, refunds, processing fees and payouts, using one ledger that also holds your other accounts and companies. Aggregate only reads from Square, it can never move money, and you choose exactly what ChatGPT can see.

Status: Live on the hosted version. Cash and other tenders recorded in Square aren't imported, because they never pass through your Square balance.

Set it up

1. Connect Square to Aggregate

Sign up at app.aggregate.finance (free during beta). Open Workspace → Connections → + More connections → Square, sign in to Square, and allow access.

2. Add Aggregate to ChatGPT

  1. Open ChatGPT Plugins, choose Add (top right), then Add custom MCP server.
  2. Name it Aggregate. Under Connection, keep Server URL and paste https://app.aggregate.finance/mcp. Authentication: OAuth.
  3. Check I understand and want to continue, select Create as a plugin, then Connect in the dialog.
  4. Sign in to Aggregate and choose what ChatGPT can see: which companies, which kinds of data, read only or read and add, and when access expires.

In a ChatGPT Business or Enterprise workspace, an admin may need to allow custom MCP servers first.

Five questions to try

  1. "How much did we sell through Square last month, after fees and refunds?" (uses query_transactions)
  2. "Which Square payouts have not shown up in the bank yet?" (uses search_transactions)
  3. "How much did Square fees cost us this year?" (uses query_transactions)
  4. "How much cash do we have across Square and the bank right now?" (uses get_overview)
  5. "Compare this month's sales with the same month last year." (uses query_transactions)

ChatGPT answers from Aggregate's ledger, where a payout and the bank deposit it becomes are matched, not added twice (a pair it isn't sure of waits in Review for you), and balances are checked against the source. Each answer can be traced to the records behind it.

Questions people ask

Does Aggregate see my password? No. You sign in on Square's own sign-in page. Aggregate stores only the access token it gets back, encrypted with a key kept outside the database.

Does my data train AI models? Aggregate never uses your data to train models and doesn't let anyone else. What ChatGPT reads is covered by OpenAI's own data policy for your plan.

Can ChatGPT move money or change my Square? No. Aggregate has no tool that pays, transfers, pays a bill or sends anything, and it only reads from Square. (Aggregate asks Square only for read permissions: payouts, payments, invoices and the merchant profile.) If you allow it, ChatGPT can add records inside Aggregate (for example a cash expense), and those can be undone for 30 days.

What does it cost? The hosted version is free while we're in beta. We may introduce paid plans later, and we'll let you know before anything changes. Self-hosting is free (AGPL-3.0).

Can I run it myself? Yes. Aggregate is open source; see self-hosting. You'll need your own Square application, or a Square access token.

Last checked 2026-11-03.

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