How to Email Receipts and Invoices to Payhawk

The current Payhawk Mailbox is a group-level intake point for forwarded expense documents. A Payhawk Administrator opens the Group dashboard, goes to Settings > Mailbox, adds the address that will forward documents, and copies the destination Payhawk generated for the company. The published example uses the @invoices.payhawk.com domain, but the example is not a template you should fill in yourself.

This matters because older Payhawk pages and search results describe a different employee workflow using paid@payhawk.me and unpaid@payhawk.me. Those pages also describe a lower attachment limit. Do not combine the old addresses with the current group-level setup. The address shown in the live account is the operational source of truth, and the current canonical Payhawk help pages are the public documentation source of truth.

Record three values before testing: the group that owns the Mailbox, the configured sending address, and the generated Payhawk destination. If the organization has several legal entities or finance inboxes, add a short description of which team controls the route. That small ownership record prevents an invoice from being forwarded from an unapproved alias or sent into the wrong company workflow.

The Mailbox is a destination, not proof that an expense is complete. A sent message still has to pass email security checks, be processed as a document, be associated with the right entity, and either match a paid expense or create the appropriate unpaid workflow. Keep those stages separate during setup and reporting.

Payhawk asks an Administrator to add the address from which documents will be forwarded. Use the real envelope sender that the receiving system will see. A shared finance address, alias, distribution group, and employee mailbox can display a friendly address while an email gateway sends from something different. Confirm the actual sender with the mail administrator when aliases or relays are involved.

Send one clear, recent invoice directly from the configured address to the generated Payhawk destination. Choose a supported PDF or image with visible supplier, date, currency, and total. Keep the original message and note the send time. A simple direct test removes Gmail or Outlook rule conditions from the first diagnosis and makes a later comparison meaningful.

Payhawk says it responds in the same email thread with the document status. A successful paid-expense match links to the expense. A successfully created bill or expense also returns a confirmation. An unmatched item directs the sender to the Pending tab. A processing failure returns a system message that can identify sender authentication, attachment count, size, format, or a general processing problem.

Conversation view can affect whether a person notices the response in Gmail or Outlook. If no response is visible, search the mailbox for the original subject and Payhawk sender before assuming the message disappeared. Then check the Payhawk Inbox with Request type > Mailbox requests. Delivery evidence should come from both the email thread and Payhawk, not only from the Sent folder.

Payhawk supports several document paths. The Mailbox fits receipts and invoices already present in email. The web portal fits documents stored on a computer and accepts drag-and-drop, file selection, or clipboard paste. The mobile app fits paper receipts, gallery images, PDF files, and documents shared from another mobile app. Agent Fetch can retrieve documents from supported vendor accounts when the feature is enabled and the required access is available.

The best workflow assigns one default path to each source. Use the Mailbox for recurring supplier emails, mobile capture for paper received at purchase, and web upload for a file finance already downloaded. Use Agent Fetch only where the current account exposes it and the vendor stores the document in an accessible online account. Parallel intake paths for the same receipt increase the chance of duplicates or wrong attachments.

Email routing remains useful even when mobile capture is available. Subscription invoices, travel receipts, marketplace confirmations, and contractor bills often arrive in shared or individual inboxes without a paper step. Conversely, an email that only says a document is ready in a portal may need a human download or an eligible Agent Fetch connection. Routing the notification alone does not create the missing evidence.

The current group-level Mailbox uses one generated destination for paid and unpaid documents. Payhawk says it identifies the correct entity from the invoice and checks whether the expense is paid. If the document is already paid, it attempts to match the evidence to an existing card transaction expense. The user still needs to inspect and submit the resulting expense as required by the company workflow.

If the invoice is unpaid, Payhawk can create a new bill expense. Its OCR extracts and suggests bill data, but the record still needs review before authorized people pay it. Payhawk may assign an owner when the invoice includes a buyer contact or when it matches a request whose owner is known. Do not promise that every forwarded invoice will produce the correct owner or a ready-to-pay bill.

An unmatched paid document is not lost by definition. Payhawk can return it as a Pending Mailbox request. The user opens the Inbox, selects the request, chooses Attach to expense, identifies the entity, and either creates a new expense or attaches the document to an existing one. The correct payment method still has to be selected when creating the expense.

Treat a success response as a starting point for downstream review. Check the entity, owner, supplier, amount, date, currency, document type, payment method, and target expense. OCR and matching reduce data entry, but the source document and company policy remain the basis for approval and payment.

For the Mailbox, Payhawk currently lists PDF documents and PNG, JPG, or JPEG image attachments. The platform also supports specified eInvoice formats, including standardized XML schemes, but those workflows deserve separate validation. A renamed or corrupt file is not valid merely because its extension looks supported. Password-protected documents must be unlocked before upload.

The current Mailbox error page documents a maximum of 40 attachments, a 20 MB combined attachment limit, and a requirement that each file be below 10 MB. These figures differ from older Payhawk material, which is why the current error documentation should be checked whenever a guide is refreshed. Split an oversized batch into smaller messages or use the Payhawk portal as the official fallback.

Multiple attachments are not merged into one document. Payhawk treats them separately, which can fragment a contractor invoice package into several review items. If one invoice has several supporting documents, Payhawk recommends combining the supporting evidence into a single PDF behind a summary invoice where that structure is appropriate for the organization. Preserve the original accounting meaning when combining files.

When there is no attachment, the Mailbox can parse the email body. That is useful for merchants that place the actual receipt in HTML email. It is not a reason to send every body-only notification. Check that the body contains usable transaction evidence rather than a login link, shipping update, marketing copy, or notice that an invoice exists elsewhere.

Payhawk publishes native forwarding instructions for both Gmail and Outlook. In Gmail, the company verifies the Payhawk forwarding address and creates a custom supplier filter. Payhawk warns that broad filters can send body-only messages, so attachment conditions are useful unless a known supplier places the receipt in the body. Outlook rules use Forward as attachment to the generated company address.

Native rules are a good fit when finance already knows the supplier, the sender is stable, the message consistently contains usable evidence, and all matching messages should go to Payhawk. They are less useful for historical catch-up, uncertain senders, mixed marketing and billing traffic, or a shared inbox where a person wants to review the first examples.

Expensent fits before Payhawk. It can find likely receipts and invoices, place them in Action Center, route reviewed messages from the connected mailbox, and create rules from a known sender and subject pattern. The Payhawk Mailbox remains the destination, and its sender, DKIM, SPF, document, and matching rules still apply. Expensent does not make an unsupported file acceptable or force a downstream match.

Avoid overlapping automation. If a Gmail filter and an Expensent rule both forward the same supplier message, Payhawk can receive duplicate evidence. Record which system owns each recurring route. Run a controlled replacement test before disabling a working rule, and check Payhawk Mailbox requests after the change.

First, complete the Payhawk Administrator setup and direct-email test. Then connect the same source inbox to Expensent and save the exact generated Payhawk destination. Label the destination with the organization or group name so a finance user can distinguish it from another Payhawk environment or a legacy address.

Run Find Invoices for a short recent date range and review the results in Action Center. Select one message that contains a clear supported document. Confirm the sender and subject, inspect the attachment or body evidence, and forward it. Keep the Payhawk response thread and inspect Request type > Mailbox requests so the first handoff is proven end to end.

Only after the result is correct should you create a recurring rule. Use the narrowest stable sender and subject pattern that represents the document stream. If a supplier sends invoices, order confirmations, newsletters, and support messages from one address, subject specificity is essential. Keep body-only and portal-only messages in review unless the exact pattern is known to contain useful evidence.

For historical catch-up, work in small vendor or date batches. Older messages may already have been uploaded through mobile, web, Agent Fetch, or another forwarding rule. Check the Payhawk expense and bill records before routing an old item. A clean inbox backlog is not worth creating duplicate accounting evidence.

A shared accounts-payable inbox can use the group-level Mailbox for recurring supplier invoices. Expensent can help finance review new sender patterns and older backlog before delivery. The team should still confirm the legal entity, owner, request reference, payment status, and OCR fields in Payhawk before approval.

An employee travel inbox can route hotel, rail, airline, and ride receipts that arrive digitally. Paper restaurant or taxi receipts remain better suited to mobile capture. If Agent Fetch is available for a vendor portal, assign one intake owner so the same document is not fetched and emailed into Payhawk independently.

A multi-entity group can centralize forwarding without pretending entity detection is infallible. Keep clear supplier and buyer details on invoices, monitor Pending requests, and require a human to resolve ambiguous entity or owner results. Historical catch-up should be divided by entity and time period rather than sent as one large mixed batch.

A month-end cleanup can search connected inboxes for receipts that never reached Payhawk. Compare candidates with missing-document reports, preserve the source email, and route only items that are still absent. The final control is the Payhawk record and accounting review, not the number of emails Expensent sent.

Expensent cannot guarantee that Payhawk accepts a message, identifies the correct entity, matches a paid expense, creates the intended bill, or extracts every field correctly. It does not control Payhawk plan or module availability, Agent Fetch, approvals, payments, exports, or accounting integrations. Those outcomes belong to the current Payhawk account and its administrators.

Payhawk native features are part of the comparison. Its Mailbox, Gmail and Outlook rules, mobile and web upload, OCR, and Agent Fetch may already cover a team with stable sources and little historical work. Expensent is valuable when the upstream inbox needs search, review, cross-message context, repeat-pattern controls, or a catch-up process before Payhawk receives the evidence.

Keep source messages until the Payhawk result has been reviewed. Monitor the forwarding mailbox for DKIM, SPF, size, count, format, and general error messages. Check Pending Mailbox requests rather than repeatedly resending the same document. Repeated sends can make the exception harder to resolve and increase duplicate risk.

Product documentation changes. Verify the live Settings > Mailbox screen and current Payhawk help before rolling the workflow across a group. If the organization still exposes employee-level paid and unpaid addresses, document that as an account-specific legacy path and obtain confirmation from the Payhawk Administrator or support team before building automation around it.