Penny — AI Bill Filer: Install, Set Up, and Test

Penny turns every bill, receipt and invoice — emailed, photographed or uploaded — into a clean transaction register: expenses coded to your chart of accounts, duplicates and payment reminders caught, and the original document filed where your accountant can find it. This guide takes you from the Awesomate Hub to a verified first filing.

Who this is for: any business drowning in supplier emails and loose receipts — trades, clinics, studios, retailers, practices. You do not need to know n8n; Penny walks you through setup in plain chat.

What it does

• Reads every bill, receipt or invoice you send it and records the supplier, total, GST and expense account in a register
  
• Codes each expense to your chart of accounts once you have loaded it
  
• Catches duplicates — payment reminders and receipts for a bill already filed are never double-entered
  
• Files the original document as evidence, one click away from each record
  
• Converts foreign-currency documents to your base currency using the official European Central Bank rate on the transaction date
  
• Answers spending questions in chat — totals, GST, top suppliers, changes against the previous period
  
• Learns from your corrections: fix a wrong expense account once and Penny prefers your choice for that supplier permanently
  

What gets installed

Redeeming a Penny bundle installs everything in one go:

• Transaction Capture pipeline — the workflow that does the filing. It arrives switched off; this is deliberate, and you turn it on in Step 5.
  
• Setup Tool — Penny's hands, used to read and write your settings. Arrives on.
  
• Penny herself — live in your Chat Hub immediately.
  
• Two data tables: transaction_records and transaction_line_items (plus expense_accounts once you load your chart of accounts).
  

Before you start

Your account also needs the standard Awesomate consents switched on (template deployment and settings writes). These are on by default — support can check if the preflight complains.

Which bundle? There are four flavours with identical brains and a different filing cabinet:

• Local Files (code TXNCAP-LOCAL-FILES-01) — documents stored on your instance. Simplest, with zero storage credentials. Recommended default.
  
• Google Workspace (code TXNCAP-GOOGLE-01) — documents in your Google Drive, with an optional Sheets mirror. Gmail intake.
  
• Microsoft 365 (code TXNCAP-MS365-01) — for Outlook and OneDrive businesses: documents in your OneDrive, with an optional Excel mirror. Intake is an Outlook category (AI/Bills) applied by an Inbox rule you create once in Outlook settings.
  
• Custom Storage (code TXNCAP-CUSTOM-01) — you bring the storage (Dropbox, S3, or an upload URL).
  

Step 1 — Redeem your bundle code

• In the Awesomate Hub, go to Settings → Redeem and enter your bundle's code.
  
• The Hub runs a preflight (plan, consents, credential matching, name conflicts) and then installs everything listed above.
  
• Credentials you already have (OpenRouter, Gmail, Drive) are connected automatically. Anything missing is listed as a credential to review — the install still completes, and you can connect it afterwards.
  

Step 2 — Say hello to Penny

Open your Chat Hub and pick 💳 Penny — AI Bill Filer. Say "Help me set up my bill filing." Penny reads your live settings first (she never guesses), then walks you through the gaps one question at a time.

Everything works on sensible defaults from the first minute — Australian GST, AUD, and the AI/Bills Gmail label — so this conversation is tuning, not assembly. There are two things worth doing in that first chat, covered in the next two steps.

Step 3 — Load your chart of accounts

This is the single highest-value step. Export your chart of accounts from your accounting software — in Xero: Accounting → Advanced → Chart of accounts → Export — and drop the CSV file into the chat. Do not paste the contents as text: chat messages cap at 5,000 characters, and the file upload loads automatically.

Penny confirms exactly how many expense accounts came in and what was skipped. From then on, every bill is coded to your accounts.

Step 4 — Tell Penny how bills will arrive

Use any or all of these intakes:

• Gmail label — anything labelled AI/Bills gets filed. The AI Email Triage template applies this label automatically if you have it; a plain Gmail filter works too.
  
• Outlook category (Microsoft 365 bundle) — anything carrying the AI/Bills category gets filed. Create one Inbox rule in Outlook (Settings → Mail → Rules, "assign category AI/Bills" for your supplier mail). Rules run when mail arrives, which is exactly when the filer looks.
  
• Filing address — give Penny an address such as bills@your-domain.com; anything forwarded there gets filed. On Microsoft 365, make your rule match that address and assign the category.
  
• Chat-drop — no setup at all: attach a receipt photo or PDF to a message to Penny.
  
• Snap page (phone) — open your-instance/webhook/penny-snap on your phone and add it to your Home Screen (iPhone: Share → Add to Home Screen; Android: Install). One tap opens the camera; snap up to a dozen receipts and send them all at once. Works whenever the pipeline is active.
  
• Webhook — for developers: POST JSON to /webhook/transaction-capture with a single file_data, a files[] batch, or plain text. Include a message_id so duplicates are detected.
  

No Gmail? If you are on Outlook, choose the Microsoft 365 bundle — same Penny, same register, with Outlook category intake and OneDrive storage. Otherwise skip the email intakes entirely; chat-drop and the webhook are fully independent.

Not in Australia? Tell Penny your tax system, currency and financial-year start — one sentence each, and she writes the settings for you.

Step 5 — Check you are ready, then activate the pipeline

Ready means all of the following, and Penny can confirm each one in chat:

• Penny answers in Chat Hub and reports your settings (this proves the Setup Tool and the AI credential work)
  
• Chart of accounts loaded — or you have consciously chosen the generic defaults
  
• The OpenRouter credential shows as connected on the pipeline's AI nodes (no red nodes)
  
• Email credential (Gmail or Outlook) connected, or the email trigger disabled (see Troubleshooting)
  
• (Google bundle) Drive connected, and a folder picked if you do not want files in the My Drive root
  
• (Microsoft bundle) OneDrive connected on the Save Evidence File node, and the AI/Bills Inbox rule created in Outlook
  

Then activate the pipeline: in n8n, open the Transaction Capture workflow and flip the toggle in the top-right corner to Active. This is the one switch Penny cannot flip for you.

Step 6 — Test it (two minutes)

• In Penny's chat, say "Run a test document through the pipeline." She fires a built-in sample invoice, waits for it to process, and shows you the resulting record.
  
• Then the real thing: drop an actual receipt photo or bill PDF into the chat. Penny submits it, waits around 30 seconds, and presents the filed record — supplier, total, GST, expense account and document link.
  
• Check the register yourself: in n8n, open Data tables → transaction_records. Every document is one row with a status:
  

Foreign currencies are handled for you. Penny reads the currency off each document; anything not in your base currency is converted using the official European Central Bank rate on the transaction date. The register keeps the original amount, the rate used (fx_rate) and the converted base_total, and all totals in Penny's reports use the converted figures.

Ask Penny where the money went: "How much did we spend this month?", "Biggest suppliers this quarter?", "Compare this FY to last." She computes exact totals, GST, changes against the previous period, top suppliers and biggest movers from your register, and can group by expense account, supplier or month.

Teach it: if a bill landed under the wrong expense account, edit that cell in the table. Penny prefers your corrections over her own guesses for that supplier, permanently.

If the email intake is on, the proof of life is simply the next real bill: it should appear in transaction_records within a minute of the label being applied, with the AI/Processed label added to the email.

Day-to-day

Nothing — that is the point. Bills arriving by email file themselves; odd ones get dropped into Penny's chat; your bookkeeper reads transaction_records (or exports it) with the evidence one click away. The export_status column sits at pending on every row, ready for the Xero-push template when it ships.

Optional: lock your filing intake. Ask Penny to set a filing key (txncap_webhook_key). Once set, only submissions carrying the key are accepted. Penny's chat-drop and test documents handle it automatically, and she will give you a personalised snap-page link to re-add to your Home Screen.

Troubleshooting and FAQ

• A bill did not file.
  
  Work through it in this order: ask Penny first ("Why didn't that bill file?") → check the document's row in transaction_records (status and notes) → check the workflow's execution list in n8n → contact Awesomate support.
  
• The pipeline will not activate because of the email trigger.
  
  If you are not using email intake, open the Transaction Capture workflow, right-click the Gmail: Bills Poll (or Outlook: Bills Poll) node and choose Deactivate. Everything else is untouched, and chat-drop, the snap page and the webhook keep working.
  
• The install listed credentials to review.
  
  That is expected when a credential (OpenRouter, Gmail, Drive) was not already on your instance. The install completes anyway — connect the missing credential in n8n, then check the pipeline's nodes are no longer red.
  
• I use Outlook, not Gmail.
  
  Choose the Microsoft 365 bundle. Intake is an Outlook category rather than a Gmail label, and documents are stored in OneDrive.
  
• I am not in Australia.
  
  Tell Penny your tax system, currency and financial-year start in chat — she updates the settings for you.
  
• A bill was coded to the wrong expense account.
  
  Edit that cell directly in transaction_records. Penny treats your correction as the rule for that supplier from then on.
  

Need Help?

Contact us at hello@awesomate.ai or raise a ticket in your Teamwork Desk portal.