Tiny Deathstars of Foulness

Server comes with a command called RoomsAdminTool located at /Applications/ This tool can list available rooms using a -l flag:

RoomsAdminTool -l

You can also create new rooms, using the following format, where krypted is the name of the room, the persistent option means the room is, er, persistent. The description option indicates a description used for the room.

RoomsAdminTool -n krypted -c persistent yes description "This room is for friends of krypted only”

To then delete the room, use the -d option:

RoomsAdminTool -n krypted -d

Add the -v to do it all verbosely. There are lots of other options as well, as follows (from the man page): Valid Configuration Keys and Values:
descriptionstringA short description for the room
passwordstringDefine a password for room entry. An empty string implies no password required.
membersOnlyyes | noOnly room members are allowed to enter the room.
subjectLockedyes | noAre non-moderators and non-admins prevented from setting the room subject
logFormatDisabled | Text | XHTMLDisable room logging, or enable it using Text or XHTML.
maxUsersinteger; 0 for unlimitedSet the maximum allowed occupants for the room.
moderatedyes | no Make the room "moderated".
nonAnonymousyes | noIf "yes", only moderators/owners can discover occupants' real JIDs.
persistentyes | noPersistent rooms stay open until they are explicitly destroyed and their configuration survives service restarts, unlike non-persistent rooms.
privateMessagesAllowedyes | no Whether or not occupants can exchange private messages within the room.
roomPublicyes | no Defines whether the room be discovered by anyone
subjectstringSet a room subject/topic
usersCanInviteyes | no Defines whether occupants can invite other users to enter the room
addOwnervalid JabberIDMake the specified user a room owner (ex.: Rooms can have multiple owners.
removeOwnervalid JabberIDRemove the specified user from the room owner list
addAdminvalid JabberIDMake the specified user a room admin
removeAdminvalid JabberIDRemove the specified user from the room admin list
addMembervalid JabberIDMake the specified user a room member
removeMembervalid JabberIDRemove the specified user from the room member list
addOutcastvalid JabberIDMake the specified user a room outcast (banned from public rooms)
removeOutcastvalid JabberIDRemove the specified user from the room outcast list
Ultimately, if you’d like to do Student Information System (SIS) integration, or wait for an AD/OD group and then programmatically generate rooms, this is how you’d do it. Also, it’s worth noting that Messages (and so Jabber if you’re running your own server) is a very basic instant messaging tool. There are more modern ways of interacting with others these days, including Slack and Confluence. Additionally, the Messages app can just use the phone number of people to let address books become a way of managing groups you’d like to message. These do not require a dedicated server, but most strategies will require a monthly fee that’s typically per-user.

September 9th, 2017

Posted In: Mac OS X Server

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I’ve worked with a lot of organizations switching between Mobile Device Management (MDM) solutions in my career. And I’ve seen the migration projects go both really, really well, and really, really poorly. In most cases, the migration is somewhat painful no matter what you do. But in this (my first) article on the JAMF blog, I try and organize my thoughts around a few things to look out for when migrating between MDMs/MAMs, and some context/experience around those. Screen Shot 2016-06-23 at 11.45.32 AM

June 23rd, 2016

Posted In: Articles and Books, iPhone, JAMF, Mac OS X

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Under the hood on iOS is a hard place to get; especially without bricking or jailbreaking a device. There are a few tools that can provide insight into what’s on a device, and about the device, though. One is an app called SysSecInfo, available at Once installed, you’ll see how much CPU and memory are in use, and not in use, on your device. IMG_9319 Scroll down and tap on Process List to see a list of each process running on the device. IMG_9961 Tap Details towards the bottom of the screen to see more information about the OS build running on the device. IMG_9320   Overall, a handle little tool, with lots of information about devices, including how to derive whether the device has been jailbroken (although note that for each method of jailbreak detection, there’s a method for defeating detection).

June 8th, 2016

Posted In: iPhone

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As with many a wearable that tracks movement, running and the such, the Apple Watch comes with… Badges. Wait, no, they’re called Trophies. No, crap, sorry, they’re called Achievements. You could just call them gamification incentives. Either way, they’re nice, they’re modern, and to me they’re a little bit more meaningful than some of the others that I’ve seen out there. As with the Fitbit, there aren’t a ton of Achievements to be had (for example, as compared to the Fuelband, which has dozens and dozens of them). There is a unique twist with the Apple Watch Achievements in that many are deferred until you’ve used the device for a few days, a few workouts or a few weeks. This way, you get a little bit of a baseline before you start breaking your own records. One of the smarter innovations, albeit a minor one – shows how much thought was put into minor details on these devices. Another interesting twist is that it primarily uses active calories, rather than just looking at all calories expended. Another twist I like a lot. So here’s how they work. Use the Activity app on the watch to track your progress. IMG_3576 When you hit an achievement, the watch tells you. IMG_3604 Use the Activity app on your iPhone to see the status of your achievements. Pretty simple. IMG_3630 Here’s a list of all of them, straight out of the Activity app:
  • First Running Workout: Awarded on your first run using the Workout app on your Apple Watch.
  • Workout Record: Awarded after the 5th calorie-based sessions with the Workout app when you hit a new record.
  • 7-Workout Week: Earned after doing at least 7 fifteen minute workouts in a single week.
  • New Record: Set a new personal record for most calories burned in a day after your first 10 days using the Apple Watch.
  • New Award: Set a new personal record for most exercise in a day after your first 10 days using the Apple Watch.
  • Move Goal 200%: If you double your daily move goal, you get this cool achievement. (awarded once)
  • Move Goal 300%: If you triple your daily move goal, you get this swanky badge, er, I mean achievement. (awarded once)
  • Move Goal 400%: If you quadruple your daily move goal, you get this award and simultaneously prove that your move goal is way too low!
  • New Move Goal: Earn your Move Goal for the first time. The easiest achievement to hit. Just hit your goal once!
  • Perfect Week (Exercise): Hit your exercise goal concurrently, every day from Monday to Sunday.
  • Perfect Week (Stand): By default, your stand goal is to stand for 10 minutes an hour for 12 hours in a day.
  • Perfect Week (Move): Hit that move goal every day from Monday to Sunday.
  • Perfect Week (All Activity): Hit all three goals from Monday to Sunday. And keep in mind. These four goals are not 7 days concurrently, but those 7.
  •  Perfect Month: Hit your goal every day from the 1st through the end of a month. Not 30 concurrent, but every day in a month.
  • Longest Move Streak: Make a new streak for concurrently hitting your move goal.
  • 100 Move Goals: Pretty cool to hit your move goal 100 times!
  • 365 Move Goals: This is similar to the Every Damn Day Trophy with a FuelBand. Except that you don’t have to hit your goal concurrently, just a total of 365 times. But you should totally go for concurrency.
  • 500 Move Goals: You get this bad boy when you hit your move goal total 500 times.
  • 1000 Move Goals: We probably won’t see anyone with this achievement for a long time. But this one means that you have hit your move goal 1000 times. Not concurrently, just total.
I’ll make this into a page accessible in a nav bar, available at here. I also have lists of FitBit and Nike badges, if you’d like to see how the three platforms stack up.

May 10th, 2015

Posted In: Apple Watch, Wearable Technology

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New in Lion Server, Profile Manager is the most substantial new service added to Mac OS X Server in recent memory. A lot of engineering has gone into it since the introduction in 10.7.0 and in 10.7.3, Profile Manager represents a service that is ready for actual deployments. I have written a number of articles about Profile Manager, but they all revolved around working with Profile Manager once the service is setup and configured. Therefore, I have decided to document the steps used to take a system out of the box and configure it for Profile Manager. Before we get started, let’s prep the system for the service. This starts with configuring a static IP address and properly configuring a host name for the server. In this example, the IP address will be and the hostname will be We’ll also be using a self-signed certificate, although it’s easy enough to generate a CSR and install it ahead of time. For the purposes of this example, we have installed Server from the App Store (and done nothing else with Server except open it the first time so it downloads all of its components from the web) and configured the static IP address using the Network System Preferences. Next, we’ll set the hostname using scutil. sudo scutil --set HostName Then the ComputerName: sudo scutil --set ComputerName And finally, the LocalHostName: sudo scutil --set LocalHostName mdm Now check changeip: sudo changeip -checkhostname The changeip command should output something similar to the following: Primary address = Current HostName = DNS HostName = The names match. There is nothing to change. dirserv:success = "success" Provided the IP address and hostname are correct, then if you don’t see the success and that the names match, you might have some DNS work to do next, according to whether you will be hosting DNS on this server as well. If you will be hosting your own DNS on the Profile Manager server, then the server’s DNS setting should be set to the IP address of the Server. I have downloaded and installed the Server Admin Tools and then opened Server Admin, connected to the server and configured just the mdm server as a single record in the zone: Provided your DNS looks just like this (your host name not mine) then changeip should work. If you’re hosting DNS on an Active Directory integrated DNS server or some other box then just make sure you have a forward and reverse record for the hostname/IP in question. Now let’s open the Server app from the Applications directory. Here, use the Next Steps drawer at the bottom and verify that the Configure Network section reads that “Your network is configured properly” as can be seen here: Profile Manager is built atop the web service, APNS and Open Directory. Therefore, let’s close the Next Steps drawer, click on the Web service and just hit start. We’re not going to configure anything else with this service in this article so as not to accidentally break Profile Manager. Do not click on anything while waiting for the service to start. While the indicator light can go away early, note that the Web service isn’t fully started until the path to the default website is shown instead of /var/empty (the correct entry, as seen here, should be /Library/Server/Web/Data/Sites/Default). If you touch anything too early then you’re gonna’ mess something up, so while I know it’s difficult to do so, be patient (honestly, it takes less than a minute, wait for it, wait for it, there!). Once the Web service is started and good, click on the View Server Web Site link at the bottom and verify that the Welcome to Lion Server page loads. Provided the Welcome to Lion Server page loads, click on the Profile Manager service. Here, click on the Configure button. At the first screen of the Configure Device Management assistant, click on Next. At the Configure Network Users and Groups screen, click on Next. At the Directory Administrator screen, provide the username and password you’d like the Open Directory administrative account to have (note, this is going to be an Open Directory Master, so this example diradmin account will be used to authenticate to Workgroup Manager if we want to make changes to the Open Directory users, groups, computers or computer groups from there). Once you’re done entering the correct information, click Next. At the Organization Information screen, enter your information (e.g. name of Organization and administrator’s email address). Keep in mind that this information will be in your certificate (and your CSR if you submit that for a non-self-signed certificate) that is used to protect both Profile Manager and Open Directory communications. Click Next. At the Confirm Settings screen, make sure the information that will be used to configure Open Directory is setup correctly. Then click Set Up (as I’ve put a nifty red circle next to – although it probably doesn’t help you find it if it’s the only button, right?). The Open Directory master is then created. Even if you’re tying this thing into something like Active Directory, this is going to be a necessary step. Once Open Directory is setup you will be prompted to provide an SSL Certificate. This can be the certificate provided when Open Directory is initially configured, which is self-signed, or you can select a certificate that you have installed using a CSR from a 3rd party provider. At this point, if you’re using a 3rd party Code Signing certificate you will want to have installed it as well. Choose a certificate from the Certificate: drop-down list and then click on Next. If using a self-signed certificate you will be prompted that the certificate isn’t signed by a 3rd party. Click Next if this is satisfactory. You will then be prompted to enter the credentials for an Apple Push Notification Service (APNS) certificate. This can be any valid AppleID. It is best to use an institutional AppleID (e.g. rather than a private one (e.g. Once you have entered a valid AppleID username and password, click Next. Provided everything is working, you’ll then be prompted that the system meets the Profile Manager requirements. Click on the Finish button to complete the assistant. When the assistant closes, you will be back at the Profile Manager screen in the Server application. Here, check the box for Sign Configuration Profiles. The Code Signing Certificate screen then appears. Here, choose the certificate from the Certificate field. Unless you’re using a 3rd party certificate there should only be one certificate in the list. Choose it and then click on OK. If you are using a 3rd party certificate then you can import it here, using the Import… selection. Now that everything you need is in place, click on the ON button to start the service and wait for it to finish starting. Once started, click on the Open Profile Manager link and the login page will open. Adminsitrators can login to Profile Manager to setup profiles and manage devices. The URL for this (for is Use the Everyone profile to automatically configure profiles for services installed on the server if you want them deployed to all users. Use custom created profiles for everything else. To enroll devices for management, use the URL (replacing the hostname with your own). Click on the Profiles tab to From Profiles, you’ll need to install a Trust profile in order for the client to enroll. Tap or click on the Install button for the Trust Profile and complete the installation process. Click back on the Devices tab. From here, click or tap on the Enroll button and complete the enrollment process on the client (following the defaults will suffice). Once enrolled, you can wipe or lock the device from the My Devices portal. Management profiles from the MDM server are then used. Devices can then opt out from management at any time. Saving these two profiles to a Mac OS X computer then allows you to automatically enroll devices into Profile Manager using Apple Configurator.

March 21st, 2012

Posted In: iPhone, Mac OS X, Mac OS X Server, Mac Security, Mass Deployment

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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). Content 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). Cradling Devices 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:
  • OTA policies and custom app deployment: MDM
  • OTA content distribution: Apps
  • Cradled policies and custom app deployment: iPhone Configuration Utility (free)
  • Cradled content and app distribution: iTunes (free)
  • OTA App distribution: AppleID/iCloud
  • Backup and restore: iCloud or iTunes
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. Apple Configurator 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:
  • Update iOS devices to the latest version of iOS.
  • Rename devices using a numbered scheme (e.g. iPad 1, iPad 2, etc).
  • Erase (wipe) iOS devices.
  • Backup and Restore iOS devices.
  • Deploy profiles/policies (e.g. no Siri for you, disable cameras, setup wireless, etc) to iOS devices.
  • Export profiles.
  • Activate devices (after all a restore of a freshly activated device is an activation).
  • Push any kind of app to devices.
  • Track Volume Purchase Program (VPP) codes used on devices.
  • Revoke VPP codes used on “Supervised” devices (more on supervision later).
  • Assign users from directory services to devices.
  • Load non-DRM’d content to apps on devices.
  • Can work with up to 30 devices simultaneously (think big USB hubs or carts on wheels here).
Apple Configurator has some caveats:
  • Paid apps need to use VPP codes to DRM apps. These VPP codes are purchased through a centralized program for an entire organization. To enter the VPP, you need to be a business with a DUNS number or an educational institution. You also basically need to be in the United States.
  • Free apps can be deployed but the AppleID is in the IPA, meaning that to do an OTA update through App Store requires entering the password for the Apple ID the app was purchased with.
  • In order to push apps through Apple Configurator, the system running Configurator needs access to Apple’s servers and Apple Configurator needs an AppleID associated with it that is not the VPP facilitator if you are leveraging any paid apps.
  • You can use Apple Configurator “off-line” or without an AppleID to Prepare devices with Profiles, just not to
  • If you push Trust and Enrollment profiles to automatically join Profile Manager (or another MDM vendor) the device isn’t associated with a user unless the MDM has been prepped to designate each UDID or Serial Number to a given user.
  • Apple Configurator doesn’t work with Video or Music due to different DRM limitations.
  • If you accidentally plug in your iPhone to a machine you’re using Apple Configurator on it and you’ve chosen to Erase in the application, then it will wipe your phone along with the 30 iPads you’re wiping. It’s awesome and scary like that (yes, I’ve accidentally wiped my phone).
I see a number of uses for Apple Configurator. Some of these use cases include:
  • Company and education labs: manage devices end-to-end (no MDM, iTunes iPhone Configuration Utility or other tools needed), managed by the lab manager.
  • One-to-One environments (schools): Manage the distribution of infrastructure settings (mail, wireless networks, etc) for devices as well as Trust Profiles to make it faster to enroll in MDM environments and Web Clips to manage the links for enrollment.
  • Device distribution: Pre-load applications (that can’t be updated unless they’re cradled again), renaming, profiles, activation, iOS software updates, etc.
  • Backup and Restore only stations where you don’t interfere with later iTunes use.
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.
Apple Configurator

Apple Configurator

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).
Configuring AppleIDs with Apple Configurator

Configuring AppleIDs with Apple Configurator

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).
Configuring AppleIDs with Apple Configurator

Configuring AppleIDs with Apple Configurator

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).
Configuring Lock Screen Settings In Apple Configurator

Configuring Lock Screen Settings In Apple Configurator

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.

Apple Configurator's Prepare Devices Screen

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.
Saving Backups in Apple Configurator

Saving Backups in Apple Configurator

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.
Preparing Devices in Apple Configurator

Preparing Devices in Apple Configurator

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.
Naming Your Profile in Apple Configurator

Naming Your Profile in Apple Configurator

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.
Adding Wireless Networks with Apple Configurator

Adding Wireless Networks with Apple Configurator

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 the URL would be 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.
Importing a Trust Profile Into Apple Configurator

Importing a Trust Profile Into Apple Configurator

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.
Show Apps in iTunes

Show Apps in iTunes

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.
Install Apps in Apple Configurator

Install Apps in Apple Configurator

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.
Adding VPP Codes in Apple Configurator

Adding VPP Codes in Apple Configurator

Once the codes are imported, you’re ready to configure a device.
App Indicator Counts

App Indicator Counts In Apple Configurator

When you import an application, you are creating a file with a GUID in /Users/admin/Library/Application Support/ These files represent applications that have been prepared for distribution. When importing, it will take as long as it takes to copy from the source to that directory. The entry in that directory is roughly the same size as the app. Therefore, you likely don’t want to copy every app you have in there, just the ones you plan to distribute.
Now for the dangerous part. Make sure you don’t have any devices plugged into the computer. I love to start with a device at the activation screen. That thing requires so many taps I jump at any 0 touch deploy type of options I can get my hands on to skip it (not that you’re going to get 0 touch if you have profiles). The reason we want to make sure there aren’t any devices plugged in is that they’ll be wiped if they are… Provided there aren’t any, click on the Prepare button and any devices plugged in wills tart configuring immediately. The application count will go down for VPP apps as each device is configured. It can do 30 in parallel.
Imaging Devices in Apple Configurator

Imaging Devices in Apple Configurator

You’ll see a green checkmark when each device is done. When you’re ready to stop configuring devices, click on Stop. The only other way to do any in parallel is through Xcode Organizer’s restore feature, but that was never very stable for this type of purpose and this is a much more object oriented approach to device imaging. The caveat for these apps is that the password for the AppleID is needed to update them, so this is not a means to deploy paid apps to BYOD or self-managed types of devices (IMHO). Also, the iOS version for devices is downloaded at this point from Apple. If you notice that the first time each type of device is imaged that it takes awhile, this is why. The second time this step is skipped (another reason we need Internet access on our Apple Configurator computer). These are located in /Users/admin/Library/Application Support/ and if you need to run a beta version of iOS you can do so by dropping their ipsw versions in here manually, but I haven’t gotten device supervision to work when doing so.
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.
Supervising Devices in Apple Configurator

Supervising Devices in Apple Configurator

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).
Device Supervision in Apple Configurator

Device Supervision in Apple Configurator

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.
Get Info on Devices in Apple Configurator

Get Info on Devices in Apple Configurator

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.
Pushing Content in Apple Configuration Utility

Pushing Content in Apple Configuration Utility

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.
Checking Devices Out To Users

Checking Devices Out To Users

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.
Choosing An App For Content

Choosing An App For Content

When you click Choose, you’ll then be able to select files to use with that application.
Selecting Content

Selecting Content

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. Conclusion 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!

March 15th, 2012

Posted In: iPhone, Mac OS X, Mac OS X Server, Mac Security, Mass Deployment

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