Did you import the certificate into your keychain? I believe Configurator looks there for some reason, rather than letting you choose a file off disk.

I did not - I couldn't find any documentation on it. I'll give it a try and let you know how it goes. Thanks!

This worked! Thanks.

Are you, by any chance, using the DEP program in 9.3? I'm using it and trying to figure out how to enroll an iPad, but I just can't figure it out. It fails with OTA enrollment with a variety of errors, and Apple Configurator flat-out refuses to work: http://i.imgur.com/pP5uxij.png

Here's where we're at: I have our server linked to the DEP. It shows the correct number of enrolled devices (still not really sure the advantage to this, unless you're buying new devices). I can prepare our devices in Configurator, and push the Configuration OTA through JAMF. What's giving me issues is the new Configurator option to enroll the device during the Prepare stage. I have our Anchor Certificate loaded into Configurator, it runs through the Prepare process with no issues, but on the iPad, when I get to the "...(our institution) can automatically configure your iPad" section of the Setup Assistant, and I press "Apply Configuration", I get an error that it's an Invalid Profile.

Here's where we're at: I have our server linked to the DEP. It shows the correct number of enrolled devices (still not really sure the advantage to this, unless you're buying new devices). I can prepare our devices in Configurator, and push the Configuration OTA through JAMF. What's giving me issues is the new Configurator option to enroll the device during the Prepare stage. I have our Anchor Certificate loaded into Configurator, it runs through the Prepare process with no issues, but on the iPad, when I get to the "...(our institution) can automatically configure your iPad" section of the Setup Assistant, and I press "Apply Configuration", I get an error that it's an Invalid Profile.