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Here's a Python script I used when I ran a SSL monitoring site: https://gist.github.com/bretwalker/5420652. It'd be easy enough to get this running as in cron job.

We use http://certalert.me/ it's free and it does multiple domains. I don't know if would have caught stripe's problem.

Yes, do it automated and do it daily or even multiple times a day.

You need to automate it if you have more than 1 site. If you have just one site, you can just check the expiry date and put that in your calendar. No need to check it on a monthly basis, no clue why the author of the post would suggest that.

Even root or intermediate certificates can be misconfigured without notice, it doesn't need to be allways the expired date case.

I don't use it for this, but the Vigil App (iOS) will monitor and report SSL errors. It's a pretty basic app, but it is also set-it-and-forget-it easy.

http://vigil-app.com/support/#ignore_ssl