When DEP nag won’t work but Setup Assistant will to enroll in your MDM

Explanation
Symptoms
Workaround
Automating
Other Considerations

Explanation

The two-days-later update: after doing troubleshooting with our MDM, asking around to other Mac admins, Google searching, and creating an enterprise case with Apple, I finally got back a definitive answer from Apple, which is that this functionality is essentially broken in Sierra (10.12.6). They're saying it should be fixed in High Sierra beta (10.13.4 right now). It makes a lot of sense. Almost all of our fleet is 10.12.6 (as of this writing, anyway), and the few computers that did work were on 10.13.2 or 10.13.3 (so not beta but still working).

So there you go. Either use the workaround below or upgrade to 10.13 if you're having this issue.

Symptoms

We have a bunch of computers that refuse to get a DEP (Device Enrollment Program) nag, even though they get the DEP prompt using Setup Assistant.

I tried blowing out a bunch of files and folders by following the Reset an enrollment section of How to troubleshoot your DEP/MDM Enrollments (on the MicroMDM blog but with generic instructions that can work for any MDM). That worked, but it requires you to go through the Setup Assistant.

I tried creating two fresh (never booted) AutoDMG-created images—one that skips the Setup Assistant and one that doesn't. If I don't skip the Setup Assistant, it obviously works. Here's the weird thing, though: if I do skip the Setup Assistant, then running

sudo profiles -N
doesn't work (skips to the next line in the terminal) and
sudo /usr/libexec/mdmclient dep nag
either gives me this error:
[ERROR] Unable to get activation record: Error Domain=NSCocoaErrorDomain Code=4097 "connection to service named com.apple.ManagedClient.cloudconfigurationd" UserInfo={NSDebugDescription=connection to service named com.apple.ManagedClient.cloudconfigurationd}
or spits back the activation record dictionary (but with no actual nag appearing):
Activation record: {
AllowPairing = 0;
AwaitDeviceConfigured = 0;
ConfigurationURL = "https://mymdmsenrollmentsurl.com/withabunchofotherstuffattheend";
IsMDMUnremovable = 1;
IsMandatory = 1;
IsSupervised = 1;
OrganizationAddress = "Our Address";
OrganizationEmail = "Our email";
OrganizationMagic = someidentifier;
OrganizationName = "Our organization name";
OrganizationPhone = Our organization phone;
SkipSetup = (
Passcode,
Registration,
Location,
Restore,
AppleID,
TOS,
Biometric,
Payment,
Zoom,
Siri,
Diagnostics,
FileVault,
iCloudDiagnostics
);
}
Now, if I actually just delete the /var/db/.AppleSetupDone file at this point and then go through the Setup Assistant, the Mac will DEP-enroll into the MDM.

So there is no network issue here (I've also tested there being no network issue on these devices by temporarily tethering them to my phone to go outside of our school's firewall—same issue).

So I really have no idea what's going on here. My MDM has all of the log information and all of my tests and insists it's not a problem on their end, but it's not the network, and it's not the image (again, a freshly created never-booted image).

Workaround

So, as yet, I don't have a solution for this. Maybe I'm the only one experiencing this. I've asked around on the Mac Admins Slack, contacted my MDM directly, contacted our Apple rep directly, done a ton of Google searches. Seems a bit weird that it's just us with a never-booted image having issues on and off network.

There is good news, though. I don't have to do Setup Assistant for every single computer or do (much worse) a factory reset on each machine to DEP-enroll it (and, yes, we have a whole deployed fleet already that needs to be DEP-enrolled).

I found that if I take the ConfigurationURL from the activation record dictionary and just put that in Safari, it will download and try to install the MDM profile in a DEP way (not just in a non-DEP way).

So the only real missing piece is the actual notification that pops up. Notifications aren't blocked (again, on a never-booted AutoDMG-created image, why would they without some custom script explicitly doing so).

Update (18/02/08): At least one other person, using another MDM, has not found this to work. Safari just loads a blank page and doesn't download and install the enrollment profile. I'm using Mosyle, and this works for Mosyle at least, as of this writing.

Automating

If that works for you (putting the ConfigurationURL in Safari and installing the profile via System Preferences), you can try also automating the workaround by having the .mobileconfig delivered as a payload to /tmp and then running a script like this as a postinstall script:

#!/bin/bash

# Install profile
/usr/bin/profiles -I -F "$3"/tmp/NAMEOFDEPPROFILE.mobileconfig
Had to run the separate profiles command because Munki will not support managing enrollment profiles.

Other Considerations

You don't have to use Safari to go to the ConfigurationURL, but it's handy to do so, because Safari, after downloading the enrollment profile, will just launch up System Preferences and try to install the profile. If you use another browser (e.g., Chrome), it will just download the profile, and you'll have to open it to get it to launch System Preferences to prompt for an install.

Yes, you can also just enroll in the MDM without using DEP, but Apple—with High Sierra's APFS default and the iMac Pro's secure boot—is moving more toward making macOS like iOS, so it's possible that DEP-enrolled devices may be treated differently or have different functionality from non-DEP-enrolled (but still MDM'ed) devices. Probably safest to do a DEP-enroll into the MDM.

Deploying Munki with Mosyle MDM

Acknowledgements: This is a slightly modified workflow based on one proposed by Taz on MacAdmins Slack. Thanks, Taz!

You can use Mosyle to install Munki.


Switch to the macOS platform (if you're not already in there).


Then, click on Management.


Scroll down to and then click on Custom Commands.


Click Add new profile.


Name it whatever you want (e.g., Install Munki), and then put in a modified version of this code:

#!/bin/bash

# Name of .pkg
munkitools='munkitools-3.1.0.3430.pkg'

# Desired hash output
desired_hash='MD5 (munkitools-3.1.0.3430.pkg) = 0afbe2fbe7cb81ff531834cba82f3a75'

# Go to the /tmp directory
/usr/bin/cd /tmp

# Download the latest Munki tools .pkg
/usr/bin/curl -L -O https://github.com/munki/munki/releases/download/v3.1.0/"$munkitools"

# Make sure the hosting server hasn't been compromised and/or the download isn't corrupted
md5_test=$(/sbin/md5 $munkitools)

if [[ "$md5_test" == "$desired_hash" ]]; then

# Install the Munki tools .pkg
/usr/sbin/installer -allowUntrusted -pkg /tmp/munkitools-3.1.0.3430.pkg -target /

# Add in basic auth info
/usr/bin/defaults write "$3"/private/var/root/Library/Preferences/ManagedInstalls AdditionalHttpHeaders -array "Authorization: Basic BASICAUTHCODE"

fi

Assign this profile to whatever devices or groups you want, and then click Save.

Any other Munki preferences (e.g., SoftwareRepoURL) you'll want to deploy in a .mobileconfig profile. More details in Importing custom .mobileconfig profiles into Mosyle MDM.

P.S. I haven't done extensive testing on this, but you may be able to deploy Munki as a .pkg and not as a custom command that downloads the .pkg. You'll have to host it somewhere yourself (and Mosyle does not like the redirect URLs, so you'll legit have to host it), but you may want to try Management > Management Profiles > Install App > Add new profile. Then, under Installation source, pick Enterprise app, and then put in the URL of the hosted Munki installer .pkg.

To change the icon, just get a .png of whatever icon you want. Here's an example of how to generate that:

sips -s format png /Applications/Managed\ Software\ Center.app/Contents/Resources/Managed\ Software\ Center.icns --out MSC.png

Only caveat is that that won't work for scripting basic authentication.

Dealing with third-party kernel extensions in macOS 10.13 (High Sierra)

If you upgrade to macOS High Sierra, third-party kernel extensions you had previously installed will be fine.

But if you didn't already have those installed and want to install them, you'll get an error like this:

There isn't a way to script that away—the user must actually click Allow.

Probably the most practical way to deal with this for large deployments is to make sure your client machines are all enrolled in an MDM.

The MDM doesn't have to do anything to the client or push any special profiles. The clients just have to be enrolled. If they're enrolled, there won't be a prompt to allow installation of third-party kexts.

Importing custom .mobileconfig profiles into Mosyle MDM

Acknowledgements: Full credit to Tom Case on the MacAdmins Slack for this tip.

It's not immediately obvious that you can import custom .mobileconfig profiles into Mosyle MDM, but apparently you can if you go to Management > Certificates > (click on profile or add new one) > Select the file.

Those can be any .mobileconfig files—they do not have to be actual certificates.

Fixing a broken MDM on OS X Server with Profile Manager

If you're getting errors like Websites are turned off. An administrator can turn them on using the Server application or the configuration for your ipad could not be downloaded invalid profile, try Reset Apache In OS X Server To Factory Defaults and then turn Websites and Profile Manager back on.

Profile Manager iOS Restrictions Restrict Profile Manager Itself!

Don't know how many Mac admins out there are actually using Server.app's Profile Manager for MDM, but I found a weird little quirk to it that's weirder than the other weird quirks about it.

iosrestrictionsprofilemanager If you disallow renaming the device by unchecking the box in iOS Restrictions, it doesn't just restrict users on the iPad from renaming the device—it also restricts Profile Manager itself from renaming the device!

So if you have some renaming you want to do on supervised devices using Profile Manager, you may want to uncheck that box. Very odd...