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My AI lost access to Pennyweight

Last verified October 9, 2026

On this page

Your AI was working with Pennyweight and now its requests fail. The connection it used has ended. You fix it by authorizing your AI again with your passphrase.

What you'll see

Your AI gets one of these replies from Pennyweight and may pass it on to you:

  • "Token rejected or expired. Re-authenticate via /.well-known/oauth-protected-resource"
  • The error code REAUTH_REQUIRED, sometimes with the message "Session invalid or expired — re-authenticate."

Both replies also tell your AI where to sign in to Pennyweight again.

In Settings → Connect your AI, under Connected AI clients, a connection that expired, or that ended because two-factor was turned off, shows Inactive. A connection you revoked there is removed from the list.

Why it happens

  • It went unused for 30 days. Each connection lasts 30 days, and the 30 days start again every time your AI uses it. After 30 days with no use, it expires.
  • You revoked it. Revoking a connection in Settings ends it right away. See manage and revoke AI access.
  • Two-factor was turned off. Turning off two-factor revokes every AI connection on your account.

How to fix it

  1. If you turned off two-factor, turn it back on first. Pennyweight won't authorize an AI without it.
  2. Start the connection again from your AI app. The steps for each app are linked from connect your AI.
  3. A Pennyweight page opens in your browser. Sign in if you're asked to, check the account email, enter your passphrase, and select Authorize.
  4. Pennyweight sends you back to your AI, which can use your data again.

If the authorize page stops you with a message instead, see can't authorize your AI.

Good to know

  • Reconnecting adds a new connection. It appears as its own row under Connected AI clients. Inactive rows from old connections stay listed.
  • Your data is unaffected. Losing an AI connection doesn't change your ledgers or your bank connections.
  • Watch the expiry date. Each active row shows when the connection expires. That date moves forward each time your AI uses Pennyweight.
  • A different message. If your AI reports "This Pennyweight account was deleted. Its data is retained for 30 days — contact support within that window to restore it; after that it is permanently removed.", reconnecting won't help. See delete your account.
  • Manage and revoke AI accessSee every AI connected to your Pennyweight account, revoke any of them from Settings, and remove Pennyweight from Claude or Gemini as well.
  • Connect your AIAdd Pennyweight to Claude, ChatGPT, Gemini or Grok with one link, then authorize it with your passphrase. How connecting works and where each guide lives.
  • Can't authorize your AIThe Pennyweight page that approves your AI stopped you with a message. Here is what each message means and how to get the connection through.
  • Turn on two-factor authentication (and why it's required)Turn on two-factor in Settings before you connect a bank or authorize your AI. Here is where to find it and what changes if you turn it off.