How do I enter/setup a regular monthly payment to a supplier such as insurance or software subscriptions?

You can create a recurring expense transaction, Premier-events.

This way, our system will automatically create these transactions every month. Here's how:

1. Click the Gear icon.
2. Choose Recurring Transaction.
3. Click New, then choose Expense under Transaction Type.
4. Click OK.
5. Set up the recurring transaction, then click Save template.

To know more about recurring transactions, please refer to this article: Create templates for recurring transactions.

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