I had issues using briefcase (latest) and encrypted forms on the kobo server. with media I had a dig around and had to reinstall briefcase v.1.11.3 to finally get some success- just incase anyone was also digging around for a solution!
Welcome to the community, @spike! Thank you for sharing this with the entire community. It should be very helpful. Maybe v1.15 should also be able to work smoothly for you. This is something the community has also shared previously that works smoothly. Maybe you could also give it a try.
Thank you!
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