Howdy 🙂
There are many reasons that this might not work as expected. The first thing that comes to my mind is that WP_CRON is not working as it should.
A simple test for that is to schedule a post for some time in the future (a couple of minutes in the future is fine) – when that’s done, navigate to the ‘posts’ screen after the post should have published. Does it actually get published or is there a ‘missed schedule’ message? See How to Schedule a Post http://www.wpbeginner.com/beginners-guide/schedule-your-posts-in-wordpress/
If WP_CRON is working, then the next thought is that a fatal error may be happening. If this is the case, I would expect evidence of that to exist in the WooCommerce logs under WooCommerce -> Status -> Logs then, in the dropdown look for any logs that begin with ‘fatal-errors’ followed by random letters/numbers, followed by a date/time. Select that, press view to get some information about any fatal errors and if they exist, take steps to get those fatal errors resolved.
If none of that helps then you may want to consider opening a support request for WooCommerce Subscriptions here: https://woocommerce.com/my-account/create-a-ticket/?form=ticket
Kind regards,
We haven’t heard back from you in a while, so I’m going to mark this as resolved – if you have any further questions, you can start a new thread.