PocketSmith integration

PocketSmith is a personal finance tool that imports transactions from your bank accounts. The Sessional integration connects the two, so you can:

• Detect invoice payments: Sessional searches your PocketSmith bank transactions for deposits that match your outstanding invoices. When found, it marks the invoice as paid and records the payment date from your bank statement.
• Categorise income: matched bank deposits are automatically categorised and labelled in PocketSmith with the invoice number and organisation name.
• Categorise expenses: Sessional matches your logged expenses to bank debits and applies the correct PocketSmith category (fuel, training, insurance, etc.).
• Auto-categorise future payments: optionally create PocketSmith category rules for each organisation you work with, so future payments are categorised automatically.

Setup takes about two minutes:

1. Connect your PocketSmith account: click “Connect to PocketSmith” on the Integrations page. You will be redirected to PocketSmith to authorise the connection.
2. Select your account: choose which PocketSmith transaction account to reconcile against. This should be the bank account your invoice payments and business expenses go through.
3. Map your categories: map each Sessional category (income, fuel, training, etc.) to one of your existing PocketSmith categories. This ensures transactions are filed where you expect them.
4. Choose your sync mode:
   • Reconcile only (recommended): matches and enriches existing bank transactions. Best if you have bank feeds connected to PocketSmith.
   • Reconcile + create missing: matches what it can, creates new transactions for unmatched items.
   • Create all transactions: creates new PocketSmith transactions for everything. Best if you do not have bank feeds and track manually.
5. Optionally enable auto-categorisation rules: Sessional will create PocketSmith category rules for each organisation you work with, so future bank deposits from those organisations are automatically categorised as income.

When you click “Reconcile now”, Sessional:

1. Loads your outstanding (issued but unpaid) invoices
2. For each invoice, searches your PocketSmith bank account for deposits matching the exact amount from the same organisation, within 90 days of the invoice date
3. When a match is found:
   • The PocketSmith transaction is labelled (e.g. sessional:INV-0042), categorised, and annotated with the invoice details
   • The Sessional invoice is marked as paid, with the payment date from your bank statement and a note that it was reconciled via PocketSmith
4. The same process runs for expenses, matching Sessional expenses to bank debits by amount and date

After reconciliation, Sessional shows you:

• Matched: invoices matched to bank deposits and marked paid, and expenses matched and categorised
• Created: transactions created in PocketSmith (push or both mode only)
• Already synced: items that were previously reconciled and skipped
• Unmatched: invoices or expenses with no matching bank transaction. This is normal for recently issued invoices or expenses paid by a different method
• Errors: any issues encountered during reconciliation

Sessional labels every PocketSmith transaction it touches (e.g. sessional:INV-0042). If it finds a transaction already labelled, it skips it. This means you can run reconciliation repeatedly without creating duplicates.

If you have bank feeds connected to PocketSmith, use “Reconcile only” mode to avoid creating duplicate transactions alongside your bank imports.

You can disconnect PocketSmith at any time from the Integrations page. Data already enriched in PocketSmith (labels, categories, notes) will remain. Invoices already marked as paid in Sessional will keep their paid status.