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Hello @thedailybark,
For WebP Image generation, we use WordPress cron. So in order to make sure the process will be completed WP_CRON should be enabled for the site. It is enabled by default, but if you have disabled it for some reason this should be reverted. You can also check if something is blocking the cron execution.
Enabling WebP will re-generate all existing WebP images, if any and will generate new WebP versions of all existing standard images.
Since you have a lot of images, the process could take some time to be completed successfully.
However, if the issue persists, please feel free to submit a support ticket in your Client Area at Siteground.
Regards,
Vladimir