Hey there. I’m really sorry for not updating you guys sooner. I have tried the permalink reset as you have described, however that did not fix the issue. This is because all of the images on my posts lead to cached links from Jetpack, and not the media library ones. The images did not start showing up in Media Library after the permalink update either.
Thank you for your time, I appreciate it. I will reach out to the Updraft Plus team.
