Do you get notified at all when this happens? I have never used stripe. I also don’t know what you’re running? Is it through a wp site? Custom stack? You could hook (API) into stripe and get immediate notifications that you set up. Then automate an email. 1. Depending on how much volume you’re doing and set up/maintenance time. If you can make more money during the same time, maybe better to hire someone part time to monitor. 2. I would set up the automations, otherwise, yes I’d check it daily. 3. You probably are not setting it up as a custom API connection? Idk how you have it set up currently? 4. I have used WPSimplepay for wp sites and it seemed to be fine and I could customize a lot. Just make sure it would work for your set up. 5. Did you ask an LLM? Screenshots and good descriptions usually produce at least a good direction to go. That’s how I learned a lot of this weird little bothersome stuff. 😂