Thank you for writing in, and I can see how you might be confused. The envelopes do not refill automatically each month. There is another step In between setting your envelope budgets and recording expenses. The missing step is your monthly refill.
To refill your Envelope with money for the month, you will need to Add Money. This function can be found on the More menu of the iPhone app, the top right of the Envelopes screen on the Android app, and under transactions on the web app.
Once you get in the groove of resetting your Envelopes at the beginning of each month, you are good to go! If you would like us to take a look at your EEBA household and offer specific help, you can email us at email@example.com with your household username.