Hi Chris, Just out of curiosity did this fix the problem long term or do you still have issues? We still have a lot of issues with the login process. I also believe it's due to having to trust the certificate for the enterprise wifi. However, we were already sending our wifi settings and certificates out via a configuration profile so this didn't fix the issue for us. Thanks, Tim ... View more

Should also ask if everyone else is running an Apple Caching Server. I think it's unlikely that we're going to get a solution from Apple but if we could at least figure out what we all have in common we might be able to figure out what is causing the issue.   ... View more

Glad to hear other people are also having this issue as both Apple and JAMF have said it's just me. The original post describes my problem exactly with the 'Login Failed Issue' - works sometimes and works after a password reset. Can I ask everyone that's posted here, are we all using the shared iPads in schools or more importantly.. Are we all using them through a proxy server? I've been wondering for some time if it's to do with the entries in our 'Proxy Exclusion List' in our proxy server. I currently exclude: .mdmenrollment.apple.com .iosapps.itunes.apple.com .icloud.com   As we are having the same issue with various MDM software it's most liely going to be Apple or a network/proxy issue.   This has been an ongoing issue with our Shared iPads and neither Apple, JAMF or Meraki seem to be able to offer any suggestions. Very frustrating. Hope we get a solution soon 🙂 Tim ... View more