If you’re interested in Mac Security, the next edition of my Enterprise Mac Security book is now shipping. You can get it here http://www.amazon.com/Enterprise-Mac-Security-OS/dp/148421711X. The book is shipping from 3rd party sellers, but should ship directly from Amazon soon at the regular price. I don’t usually know exactly when, but it should also appear for Kindle and on the Apple Books store as well. Hope you enjoy!
krypted January 12th, 2016
I was super-bummed that I missed the MacAdmins conference at Penn State University. But, all is not lost as MacAdmins will be held July 8-10 in 2015 at the Penn Stater Conference Center and I’ll be able to see all those awesome people there next year!
In the meantime, something fun and new is the 2014 MacAdmins Playlist to maybe get exposed to some new stuff: http://spoti.fi/VTdxLX.
As an aside, here’s a fun pic of @derflounder and I (and others) doing a round table from a few years ago on the Penn State site:
krypted July 15th, 2014
Learn some stuff! For Free!
There are so many resources available for learning these days that it’s hard to keep track of it all, or to find the things that are actually worth doing. So I decided to make a list of some of my favorites:
krypted May 20th, 2014
Posted In: Articles and Books
My traditional interpretation of Apple’s vision on how iOS devices are used is that everyone has an AppleID. That AppleID enables them to access their apps from any iOS device they own or Mac that they own. That AppleID enables them to access mail, contacts, calendars and even files through iCloud. That AppleID also allows users to remotely wipe their device through Find iPhone and track their friends iOS devices (as in social networking via breadcrumb tracking) through Find Friends. All of this “Just Works” in a consumer sense. And it even allows for a little sharing of content across devices you own. However, larger organizations need more. They need centralized management, content distribution and most other things you find that you rely on traditional desktop computers for.
Over the years, Apple has added tools for centralized control of devices. This started with ActiveSync compatibility and early forms of Mobile Device Management and has grown into a pretty robust, albeit disconnected, set of tools. Of these, Apple Configurator is the latest. Apple Configurator was released about a week ago and since, I’ve been trying to figure where it fits into the solutions architecture that surrounds iOS integrations. There are a number of other tools already available that can aid in the deployment and management of iOS devices, and Configurator is a great addition.
To me, there are 3 classes of management tools for iOS. These were roughly broken up into Over the Air (OTA), cradled (USB) and content management. Apple Configurator ends up fitting into all of these scenarios in some way. Let’s start by looking at the traditional uses of these three and then look at how they are impacted by Apple Configurator.
Mobile Device Management
Over the Air tools, such as Profile Manager, allow for Mobile Device Management (MDM) without cradling, or syncing a devices. These tools allow you to configure policies via profiles. There is also a bit of App pushing built into most MDM solutions. Apple’s Profile Manager can push applications written in-house, but no content from the App Store. 3rd party solutions, such as JAMF’s Casper Suite, Absolute Manage MDM, AirWatch and about 15 others are able to push apps from the App Store as well, leveraging the Volume Purchasing Program (VPP) to issue apps to devices. However, when an app is pushed through one of these tools, the app becomes associated with the AppleID for the user who owns the device.
Note: While we use the term push, the user has to accept all App installations on the device.
For large environments, MDM is a must as it allows for centralized command and control. Pushing apps is one aspect of such control. Policies enforceable through MDM include disabling cameras, configuring passcode policies on devices (not pushing passcodes), disabling YouTube, silencing Siri, unstreaming photos, disabling iCloud Backup, forcing encrypted backups, disabling location services, controlling certificates, blocking pop-ups, controlling cookies, disabling access to the iTunes and App Stores, and controlling what kind of media can be accessed on devices.
Additionally, MDM can be used to push SSIDs for wireless networks (and their passwords/802.1x configuration information), setup mail, setup Exchange ActiveSync, configure VPN connections, configure access shared calendars (iCal shared files, CalDAV and Exchange), configure access to shared contacts (LDAP, CardDAV, Exchange and Exchange Global Address Lists), deploy Web Clips and manage certificates (either with cert files or via SCEP). In short, whether you’re using the practically free Profile Manager from Apple, Mobile Iron, Casper, AirWatch, FileWave or one of the many other tools, there are a lot of things that MDM can configure on devices.
Reporting can also play a major role in how MDM tools are used. iOS Apps are owned by AppleIDs, not devices. MDM does not manage AppleIDs, but you can trigger fields in MDM databases to report back unauthorized AppleIDs being used. Reporting can also identify when devices join non-approved wireless networks (which cannot be blocked through MDM), identify devices that have been jailbroken (a major security concern for many organizations) and report on device use.
Because devices can fall outside of our control, MDM also plays an important role in being able to wipe and lock devices. While some of these types of features are available via Exchange, not all people use ActiveSync. Users and administrators alike can wipe, lock and de-enroll devices at will, potentially crippling what any device with an Enrollment Profile can do.
There are really 3 kinds of MDM tools: those that can push apps, those that can’t and Apple’s Profile Manager. The reason I put Profile Manager into its own class, is that it can push some kinds of apps, it’s cheap ($49.99 one time as opposed to per device per month or per device per year billing) and it’s great for some things. But Profile Manager should be used in very specific environments unless the price is the only decision making factor behind a tool. In larger environments, choosing a MDM solution is one of the most important aspects of managing mobile devices and the iOS platform is no different in that manner than other mobile platforms.
MDM has some limitations, though. A good MDM solution can manage the infrastructure side of device configuration. However, content requires a completely separate tool. Additonally, MDM is a completely opt-in experience. If a user wants, they can remove their device from the MDM solution at any time. Rather than a limitation, think about the opt-in experience this way: if a user removes themselves from MDM then all content that was given to them via MDM is then taken away, except that which they have moved to the local device. Therefore, if an administrator pushes an Exchange configuration then all content from that Exchange profile is forbidden fruit, removed alongside the de-enrollment.
MDM also works with Lion. Policies, centralized management, etc can be integrated with Lion. You can’t do app distribution per se, but you can push out a policy to change where the dock is on the screen, add a printer to a Mac and configure a login hook through a Profile Manager-based policy. Many of the MDM providers have begun adding functionality to their tools to allow for Mac management as well as iOS and I would expect that to become the standard in years to come. iOS is a single-user device and OS X is a multi-user device, which completes that paradigm, but Apple has made it no secret that policy-based management for Mac OS X is moving to the realm MDM (even if that is enforced through a traditional lens of directory services based policy-based management).
One of the unique aspects of the iOS platform is that it doesn’t have a file system that is exposed to users. There’s no /Volumes, no C: drive and no home folders. The devices don’t log into a server, because there’s no way to interpret a server connection. The file system that is exposed to iOS devices is through the lens of each application. Sandbox is a technology that limits each application’s access in terms of memory, hard drive, etc. Each application can only communicate with resources outside of itself if there is an API to do so, APIs mostly reserved for Apple (e.g. photos, contacts, etc). Therefore, when you discuss content management from the perspective of building a large iOS solution, you’re talking about apps.
The apps used for content management come in a few flavors. There are those that allow you to edit content and then there are those that allow you to read content. One way to look at this is through Safari. Sharepoint, WebDAV and various document management portals allow users to access data through the Safari browser on an iOS device. Safari will let you view various file types. But to edit the data, you would need to send it to an app, or copy it to the clipboard and access it in an app. Pages is an example of an app that can browse a file tree via WebDAV and edit content. However, planning how each type of file is accessed and what type of editing can be done on each file type or what type of resources need to be accessible can be difficult (e.g. there are a number of transitions in Keynote presentations that do not work in iOS).
Then there’s iTunes. iTunes allows you to backup and restore devices, update devices, etc. iTunes allows you to drop content into each application. If you look into the ~/Library/Mobile Documents, you can drop content, edit default documents and other tasks that can be done through a command line, then perform a cradled sync to an app. If networking is built into an app then you don’t have to plug a device into a computer. If an app can leverage iCloud, SMB or AFP then you can access data over the air. If you are trying to replace computers with iOS devices (a la post-PC) then you would need to plan each business task that needs to be performed and make sure not only that there is an app for that (or an app you build for that) but also make sure that you can round trip data from a shared repository and back to the network storage that the data resides on.
You can also access many of the benefits of MDM without having an OTA element. This can be done with iPhone Configuration Utility. iPhone Configuration Utility can configure the same policies available through Profile Manager but relies on either a cradled or email/web server/manual way of getting policies onto devices and updating. MDM automates this, but iPhone Configuration Utility is free and can be used as well. Additionally, profiles can be exported from Profile Manager and installed in the email/web server/manual way that iPhone Configuration Utility profiles are installed.
This is all probably starting to seem terribly complicated. Let’s simplify it:
Basically, there’s a few holes here. First, AppleIDs cannot be centrally managed. Second, you need to use gift cards or the Volume Purchasing Program (VPP) to distribute apps, and Third, even when you push an app to an AppleID, the app follows the AppleID to their next organization (which causes many organizations to treat apps like consumables). Fourth, synchronizing content is done primarily through iTunes, which only syncs a device at a time, making preparation of large numbers of systems terribly complicated.
Enter Apple Configurator, a free tool on the Mac App Store. This tool basically fixes all of the problems that we reference, but does so over USB. This means that Apple Configurator is not necessarily a replacement for MDM. In fact, you can deploy Trust and Entrollment profiles for MDM and automate the MDM enrollment for a device through Configurator. Instead, Apple Configurator is a tool that can either Prepare or Supervise an iOS deployment and do so in a manner that is easy enough that you don’t need a firm background in IT to manage devices on a day-to-day basis.
Here is what Apple Configurator can do:
Apple Configurator has some caveats:
I see a number of uses for Apple Configurator. Some of these use cases include:
These can enhance practically every environment I’ve worked with. But unless it’s a small environment (e.g. the labs), Apple Configurator isn’t a replacement for the tools already in use in most cases. Instead, it just makes things better. Overall, Apple Configurator is a welcome addition to the bat belt that we all have for iOS management and deployment. Now that we’ve looked at the when/where of using it, let’s look at the how.
There are two ways to use Apple Configurator. The first is to Prepare Devices. You would use this mode when you’re going to perform the initial setup and configuration of devices but not when the devices won’t be checking back into the computer running Apple Configurator routinely. Preparation settings do not persist. And while applications can be pushed through Preparation, updates for those applications will be tied to the AppleID that purchased the app.
The second is Supervise. Supervising devices is an option when preparing and allows you to have persistent changes to devices, to layer new settings the next time devices are plugged in, to add applications and the most intriguing aspect of iOS management here is reallocating VPP codes to new devices when a user or device is retired. Supervising devices also allows for assigning a given user to a device and thus pushing data into an application.
Setting Up Apple Configurator
Apple Configurator is installed through the Mac App Store. When installed, you are presented with three options. The first (going from left to right) is to Prepare Devices.
Before we get started, we’re going to add our AppleID. The computer running Apple Configurator needs to be able to connect to the App Store and it needs to have an AppleID associated with it if you’re going to use VPP codes. So let’s set that up before moving on. To do so, from Apple Configurator, click on the Apple Configurator menu and click on Preferences… From the Preferences menu, click on Set for the Apple ID and provide an AppleID (not the VPP Program Facilitator).
Then, when prompted, provide the credentials for your AppleID. If you have any problems with this, try Authorizing the computer in iTunes, if you can’t do one it stands to reason you can’t do the other and it’s either an invalid AppleID or that the computer cannot communicate with Apple’s servers (ports, DNS, Internet connectivity, etc might be the issue).
Also, let’s configure the Lock Screen settings, which is what’s displayed to users when you’re supervising devices. If you have user pictures in Open Directory, this will show each user’s photo at the lock screen (we will discuss device supervision later).
Using Apple Configurator to Prepare Devices
In this example, we’re going to prepare some devices for deployment. Before we do anything, we’re going to do a backup of the iOS device to use for testing. To do so, simply click Prepare Devices to bring up the main Apple Configurator screen and then click in the Restore field.
At the Restore menu, click Back Up…
Then choose the device to backup and click on Create Backup… to bring up the screen to select where to save your backup to (by default it should be your Documents but you can save them anywhere, like /iOSBackups). Click Save to make the first backup.
Notice how fast that went (assuming you didn’t load it up with 10 Gigs of crap)? The reason is that we’re not backing up iOS, just the data. This will become a little more obvious the first time we go to restore a device. In the meantime, if you look at your target directory, you’ll see a file with the name you provided followed by .iosdevicebackup. If you aren’t supervising you would need to delete these from the filesystem to remove them from the menu of available backups. If you are supervising then you’ll have a menu to manage the backups. You can also use the Other option in the selection menu to browse to another location and select another backup (e.g. you’re pulling them from other machines, etc.
Now that we have a backup, let’s do some stuff to the device. Let’s join the wireless network, change the wallpaper, create some contacts, make some notes and in general do some of those things that you might do on a base image of a computer, aside from of course configuring local admin (it’s not a multi-user device), installing anti-virus (to date, AV companies for iOS are snake oil salesmen) and other things you might not do. But as with imaging, if you can do something in Profile Manager or Apple Configurator, let’s reserve doing it there. In fact, I would probably try to set everything in Profile Manager or your MDM provider that you can (if you have one) and use Apple Configurator for as little as possible. That goes with imaging as well, do as much in directory services/managed preferences/profiles as you can and keep the image as simple as possible…
Anyway, once you have the device as you want it, make another backup. This is akin to baking an image with DeployStudio or System Image Utility. We can’t asr them out yet, but we’re in a much better place than we were.
Once you have a good backup, let’s leverage Apple Configurator to tell the device erase, update to the latest version of iOS, restore our image, join the SSID of our enrollment network (let’s consider this similar to a supplicant network in 802.1x). Then, let’s add a profile that will throw a Web Clip to our MDM solution and even add a Trust Profile to cut down on the number of taps to enroll (and the confusion of tap here, tap there, etc). From the Prepare screen in Apple Configurator, click on Settings and type the naming convention for your devices (in this case we’re going to call them krypted 1 and up) in the Name field. Then check the box for Number sequentially starting at 1 so it’s going to name them from 1 to 1,000,000 (which is how many iPads my krypted company is going to end up writing off at the testing rate I’m on now). Leave Supervision set to OFF (we’ll look at that later) and set the iOS field to Latest. Then, check the box for Erase all contents and settings and choose your image from the Restore menu.
Now for something that users of iPhone Configuration Utility, Profile Manager and Casper MDM will find familiar, click on the plus sign in the Profiles field and select Create New Profile. Here, we see what is the standard policy sheet (apologies to HIG if that’s not what those are officially called but I’ve not been able to find the right term) and give it a name in the Name field. This is how it will appear in the Profiles section of Apple Configurator. Because you can deploy multiple profiles, I’m just going to configure the SSID and Web Clip and call it MDM Enrollment. Optionally, give it some notes, organization name, etc.
Click on Wi-Fi and then click on the Configure button. Here, enter the SSID of the deployment network (MDMEnroll in this example). We’ll use the Hidden Network field to indicate the SSID is suppressed and we’ll use the network type of WEP and throw the password into the Password field as well. Now, before we move on, notice that there’s a plus and minus sign in the top right of the screen? You can deploy multiple of each, so if you have 10 wireless networks, 4 Email accounts, 9 VPN connections, 29 SSL Certs etc, you could deploy them all easily with multiple entries of each.
Scroll down in the sidebar a little and then click on Web Clips. Click on the Configure button. The Label is how the web clip’s name will appear on the device. We’re going to enter Enroll Here. In the URL field, provide the URL for your MDM server (e.g. When using a Profile Manager server called mdm.krypted.com the URL would be https://mdm.krypted.com/MyDevices). Not to get off topic, but did anyone else notice that Profile Manager in 10.7.3 now requires SSL certs? Anyway, you’ll also choose whether the web clip should be Removable (I think it should if it’s to enroll) and optionally choose an Icon. We’ll skip that (if we were using a 3rd party tool, I’d throw their logo in here; otherwise I usually like to use the company logo. I also like enrollment links to be Full Screen.
Go ahead and click Save and you’ll see MDM Enrollment listed in the Settings. If you notice, you can also click on the profile and then click on the export menu to export the profile or under the plus sign (“+”) you can Import Profile…, which is how we’ll bring in our Trust Profile from Profile Manager. From Profile Manager we already downloaded the Trust Profile. Now we’re going to click on Import Profile… and browse to it on the desktop, clicking on Trust profile.mobileconfig (or whatever name yours may have). Click Open.
We could go a step further and actually enroll the device by exporting the enrollment profile as well, but again, I want each user to provide their username and password so I as an administrator don’t have to go through and attach each device to a user in this scenario. I’ve been looking at importing devices and associating them with users via postgres, but that’s going to be another 3am article, on another night…
Next, check the box for each profile and click on Apps. This is where things start getting kinda’ cool. For this you’re going to need some app ipas. Each app in iTunes is stored as an .ipa file. We’re going to look at two different kinds of apps. The first is a free one and the second is a paid for app, both we’ll pull from iTunes. To do so, open iTunes and click on an app (iBooks in our example) and click on Show in Finder.
Note: Not all app .ipas are called the same thing as the filename. If you Show in Finder from the contextual menu of an app in iTunes it will automatically highlight the correct app in the Finder when it opens a Finder screen.
From the Finder you can either copy the app to the machine running Apple Configurator or if you’re using iTunes on that machine, you can go ahead and drag it to the Apple Configurator apps list. We’re also going to add an App that we used a purchase code from the VPP store to buy. You’ll get an error when you drag the paid app in (or browse to it if you so choose) that indicates the app is paid and in order to deploy it you’ll need to use VPP codes. Once added, you’ll notice it has an error indicator and the number 0 beside it.
Click on the numerical indicator beside the app name and you’ll be able to import redemption codes. These are emailed to you when you buy apps through the Volume Purchasing Program. BTW, no drag and drop in this screen, use the Important Redemption Codes button to browse to the XLS files.
Using Apple Configurator to Supervise Devices
Now, supervising devices may seem more complicated, but it isn’t. Back at the Prepare screen, we set Supervision to OFF. Change the iOS field to No Change. Now, let’s turn it ON. When you do so, the iOS field automatically switches to Latest. This means that supervision is going to require updates (which is fine in my book as updates have yet to break a single app for me). Get all the same settings the same as they were previously.
Once you enable Supervision, click on Prepare in Apple Configurator and connect a device again. The device will then be imaged as with the same settings that you’ve given it from before. However, once it’s done, you’ll be able to click on the Supervise tab and see devices (Note: You supervise devices rather than users).
The subsequent Starts and Stops will now allow you to enable and disable profiles and apps on the fly, as well as restore backups, update devices and as you can see in this screen, reclaim those valuable VPP codes!
Do a Get Info on a device and you’ll also see a bevy of information about that device.
You can also click on Assign, once you’ve enabled Supervision. Assigning devices requires directory services. When you click on Assign, click on the plus sign (“+”) to add the first user. Type the first few letters of the users name and they should appear in the list. Click on them and they’ll be added. You can then use the right panel to assign content to the apps that you assign to that user’s devices.
Once added, the user will by default have no device. To assign a device to a user, use the Check Out box at the bottom of the screen and then match the users with the devices you want them to have.
The final piece of this application is to assign content to users. As I mentioned earlier in this article, the file system of an iOS device is through the lens of the applications that the device has installed. Therefore, we’ll be associating files to applications. DRMd content is not distributed through Apple Configurator. So iBooks, etc, aren’t applicable. The various third party applications can open and therefore host file types that they support, as with iTunes. From the Assign pane of Apple Configurator, click on a user and then click on the plus sign (“+”) to add documents. At the Choose A Target Application screen, choose the application you’ll be loading content into.
When you click Choose, you’ll then be able to select files to use with that application.
Then just dock the iOS device, sync and viola you’ve got content distribution over USB all handled. You can also add groups of devices and groups of users and distribute content to groups of users rather than to one at a time.
Apple Configurator is really a great tool when used in the right scenarios. In learning how it works and interacts I actually learned a lot about both iOS and Mac OS X that I didn’t know before. I hope I did the tool justice with how easy it is to use. This is a fairly long article and it’s probably more complicated than it needs to be in parts, but that’s more my method of trying to figure out what it’s doing than the tool being complicated. It’s not hard to figure out at all. I am sure I could teach any non-technical iOS admin to use it in less than an hour.
My wish list includes logs and OTA. You can’t use iPhone Configuration Utility while you’re using Apple Configurator and therefore, you can’s see up-to-the second logs about things like key bags to figure out why this isn’t working or that. This makes it kinda’ difficult to figure out why a profile doesn’t get installed with an image if you’re not using an AppleID with the tool or other weird little things like that. I’d love to see a little more logging. Obviously, if you could run this thing Over the Air then it would be nerd nirvana. I guess the OTA isn’t as much as wish list for this tool, but features that could be imported into Profile Manager and other tools.
One of the more important aspects is the impact on AppleID use and app ownership. I started this off by saying “My traditional interpretation of Apple’s vision on how iOS devices are used is that everyone has an AppleID.” Well, when using this tool an AppleID is no longer necessary for app deployment.
Overall, we have a new, powerful tool in our arsenal that makes up the iOS administration ecosystem. I hope that I’ve managed to dispel a few rumors with this article and look at some great uses for where this tool should and should not be used. I also hope that no matter what, if you manage iOS devices, that you’ll take a look at it. I expect you’ll find it useful in some part of your management toolkit!
krypted March 15th, 2012
Tags: 802.1x, ActiveSync, AFP, API, Apple, Apple Configurator, AppleID, applications, apps, carddav, company, content management, cradle, deployment, devices, distribution, DRM, DUNS, education, encrypted backups, Exchange, iCloud, ios, iPad, iPhone, iphone configuration utility, ipod touch, itunes, LDAP, lock, management, mdm, mobile device management, mobility, ota, over the air, Prepare, reporting, restore, revoke apps, Safari, SCEP, schools, serial number, sharepoint, SMB, Supervise Devices, Trust Profile, UDID, volume purchasing program, vpn, vpp, Web Clip, webdav, wipe, Wireless