DEP Enrollment not prompting over wireless network

[lisamcray]

Has any experienced an issue with DEP enrollment not prompting over wireless?

We are testing with a new Macbook Pro that was set up for pre-stage enrollment with DEP. During out of the box set up, we are able to select and successfully connect to the wireless network.

After connecting to the wireless, we proceeded through "Setting up your Mac" and received the standard prompts, expecting at some point to be prompted for DEP, but never were.

Confused by this we began hitting the back button until we returned to the "Select Your WiFi Network" screen. We clicked continue and only then did we receive the prompt for DEP.

We were able to reproduce this behavior several times. There seems to be a large delay between when the wireless network connection is established and when the machine picks up enrollment in DEP. If you've already clicked "Continue" you are never prompted for DEP.

Anyone have any thoughts on this? There is a really good chance that our laptops will miss out on DEP enrollment if this is the default behavior.

Thanks!

[pkim]

We are actually experiencing an issue where the DEP is not contacting the MDM server.

[flojo10]

I've seen this, but not specific to WiFi (we always connect our Macs to the LAN). Sometimes it'll take a few minutes or a disconnect/reconnect to the network. Our current workaround is that we have a failsafe policy that only runs if the Mac misses PreStage enrollment. It contains most of the stuff that PreStage sets beforehand; we're just preparing to tell our users that this might occur. The scope for the failsafe is scoped to a smart group that has computers that didn't enroll through DEP. Likewise, that non-DEP smart group is excluded from the regular first step of our enrollment process.

[lisamcray]

@flojo10 Are you manually installing Casper on these machines when DEP fails?

[wbarnes01]

We ran into this when setting up some Macbook Pros. The prestage enrollment wasn't coming down for the computers that we pulled out of storage. Since the computers were in storage their batteries had run down and the time/date on the computers had reset to 2001. When the time/date were off by significant amounts we were unable to get the prompt for DEP prestage enrollment during the Apple Setup screens when starting the computers up.

Getting the computers on the current date/time resolved the issue and we would have the prestage enrollment install after choosing a wifi network to connect to. When the prestage enrollment failed to install we could get it to install by running through the Apple Setup again once the time/date was fixed.

[nigelg]

I am experiencing an issue with a MacBook not downloading the MDM profile. It says "A problem occurred while obtaining automatic configuration settings". It can also say "Failed to contact the MDM server".

This is after it tells me there is a configuration available. Its the first OS X device I have tried using DEP with. I have checked the time on the device and it is correct so thats not the issue.

[lisamcray]

From the replies, it seems that there are some real challenges with DEP enrollment with Casper across the board. However, we are not having an issue with time on our devices. Is anyone else having the specific issue that I detailed above, DEP Enrollment not prompting over wireless network, and if so how have you fixed it? Thank you so much for your help!

[flojo10]

@lisamcray

We don't install any of the Casper Suite (Imaging or otherwise) onto our end user's machines. If DEP fails, enrollment still kicks off (worst case we have to have the user go to the /enroll to install the QuickAdd package). Following that, the things we have configured in PreStage are done via the first step, although the users have to go through the extra Apple Setup screens. I guess it really depends on what you have configured in PreStage, and how important it is that your users bypass those extra steps during Apple Setup.

@nigelg

I had a similar issue, but after issuing the SSL cert and renewing the DEP token, the issue was resolved.