Automate downloading internet bill & uploading for reimbursement

Hi MPUers,

A good friend of mine (not an automation nerd) recently asked me about how we can achieve downloading his internet bill and upload it to a website for reimbursement. I could think of Keyboard Maestro as a way to accomplish this by clicking specific buttons by image matching. However, they don’t want a paid app for this.

Any other way this can be accomplished without KM? Any suggestions?

This is all so dependent on external factors that it is probably not possible to get a single answer. We don’t know the sites, we don’t know how the bill is accessed, we don’t know where and how it is later uploaded, etc.

If you want free, then play around with Automator. Data from sites can be downloaded. As far as the upload, I don’t think Automator can do that – it’s obviously a security issue and sending data to some random website could be construed as spamming or, at worst, a DOS attempt, no matter how benign the intent. But Automator can send emails, so that might be an option. Beyond Automator, you can probably be more precise with AppleScript.

Or why not just set a recurring task in Reminders: “get my bill; pay my bill”.