Tag Archives: deployment

Articles and Books Mac OS X Server

Chapter 3 Of My Next Book Available

The next chapter of my next book is again available free for TidBits readers at http://tidbits.com/article/14799:

This article is a pre-release chapter in the upcoming “Take Control of OS X Server,” by Charles Edge, scheduled for public release later in 2014. Apart from “Chapter 1: Introducing OS X Server,” and “Chapter 2: Choosing Server Hardware,” these chapters are available only to TidBITS members; see “‘Take Control of OS X Server’ Streaming in TidBITS” for details.

Hope you enjoy! And thanks again to Adam and Tanya for their awesome editorial!

Mac OS X Mac OS X Server Mac Security Mass Deployment public speaking

MacSysAdmin 2014!

Well, it’s that time of the year when one of my favorite conferences opens up registration! Come one, come all to MacSysAdmin for good times, good people and lots of fun Macinnerdiness! I hope to see you there! The official page is up at http://www.macsysadmin.se.
Screen Shot 2014-04-13 at 8.02.49 PM

Mac OS X Mass Deployment

Enable Safari Status Bar Using Defaults

Nice and easy one today. By default, the Safari status bar is disabled at the bottom of a Safari screen. To enable:

defaults write com.apple.Safari ShowStatusBar -boolean YES

iPhone Mac OS X Mac OS X Server

Apple ID Bulk Importer

Some iOS and/or OS X deployments require us to create a boatload of Apple IDs. This could be to redeem VPP codes, to do iOS backups, to configure Messages, now giving the ability for OS X Server users to password reset for themselves, etc. I have sat and manually created Apple IDs for a number of clients. I’ve created dozens at a single sitting and there are some serious annoyances and challenges with doing so manually. For example, you’re gonna’ fat finger something. If you type 10 things in for 50 accounts then it’s hard to imagine you’re not gonna’ mess something up in one of those 500 fields. It’s also time consuming and well, just annoying.
AppIcon

Then, along came a script. That script allowed us to create loads of IDs on the fly. Now, we have a very nice GUI tool called the Apple ID Automation Builder that can be used to batch create a number of Apple IDs on the fly. Brought to us by Greg Moore and hosted by enterpriseios.com, this is one of those rare finds that is a serious time saver and very valuable when you need it in your bat belt. Great little tool, well worth the money and I look forward to providing Greg with plenty of accolades should we ever meet!

iPhone Mac OS X Mass Deployment

JAMF Nation User Conference 2012

JAMF has announced the 2012 rendition of their National User Conference. Having been to two of these, I can say that if you use any JAMF products that it is a great event to attend. It is a lot of very specific information about integrating, mass deploying, mass managing, mass document distributing and mass 3rd partying for Apple products.

The National User Conference will be held October 23-25 2012, 8:00 am – 5:00 pm in beautiful Minneapolis, Minnesota (where all the cool kids live). The venue is one of the best conference spots I’ve seen in the Guthrie theater, overlooking the stone arch bridge. In previous years, there have been announcements, new versions, people discussing their specific integrations, etc. I would also think that if you use another product that you might find the conference helpful, as you get to see whether the grass really is greener on the other side!

Anyway, I recommend coming out to Minneapolis for this one if you can. And if you do, let me know!

Mass Deployment

Deploying and Managing Firefox Part 2: Working with Munki

A special thanks to Nick McSpadden for his third submission to krypted.com. With all the new changes in OS X/Server I haven’t even had time to write as many in such a span!!!

This is a follow up post to the Firefox Management guide.

Knowing how to use the CCK to manage Firefox, the next big question is: how do we get this into Munki? It’s unfortunately not as cut and paste as we’d hope, because, with all things, Firefox tends to make us do a bit of work to get what we want from it.

Importing Firefox 10.0.10 ESR (current version as of writing time) into Munki is easy. You can add whatever other stuff you need to the pkginfo, but it tends to take care of itself.

Importing the CCK into Firefox is where this gets fun. Luckily, some very smart people have figured this out, thanks to the MacEnterprise mailing list. See the conversation here: https://groups.google.com/d/topic/macenterprise/YUqrm96QSFo/discussion. Credit goes to Nate Walck for the script and Greg Neagle for the advice.

If you are deploying the CCK into the internal Firefox application distribution directory, then you may notice that a vanilla install of Firefox does not have the Firefox.app/Contents/MacOS/distribution/bundles/ directories. We’ll have to create them as part of the install process.

If you want to put the Firefox CCK files somewhere other than inside Firefox, you’d need to change the add-on scopes for Firefox to load it. This isn’t really ideal either, because it requires micromanaging the Firefox install, which means that every time you import a new Firefox update, you have to do a lot of manual labor to make sure all these preferences get included.

One solution is to repackage Firefox with the CCK itself and deploy that as one. It works just fine, but it’s a lot of work – especially with Firefox’s release schedule. You’d have to rebundle it for Munki every six weeks. Pox on that, I say. But editing Firefox preferences is also undesirable for the extra work it generates.

Greg’s suggestion: a symlink! Throw the CCK anywhere, such as /Library/Application Support/FirefoxCCK/, and then create a symlink into Firefox’s bundles directory.  In this post, I’ll be using the example CCK configuration named “test-sacredsf-cck@extensions.sacredsf.org” as in my last post.

There are a few pieces to this we need to incorporate:

  1. A postinstall script for Firefox that guarantees the establishment of the symbolic link between the CCK location and the internal Firefox bundles directory.
  2. A package for the CCK itself that drops the items in the location you want, with the appropriate installs key to ensure it reinstalls if deleted.
  3. The CCK package should also establish a symbolic link to itself if one does not already exist.
  4. A guaranteed reinstall of Firefox, should it be deleted, that also incorporates the re-establishment of the symbolic link.

We can accomplish part of this in a postinstall script for Firefox in Munki:

#!/bin/bash
mkdir -p -m 755 /Applications/Firefox.app/Contents/MacOS/distribution/bundles/
mkdir -p -m 755 /Library/Application Support/FirefoxCCK/
if [ ! -L /Applications/Firefox.app/Contents/MacOS/distribution/bundles/test-sacredsf-cck@extensions.sacredsf.org ];
then
 ln -s /Library/Application Support/FirefoxCCK/test-sacredsf-cck@extensions.sacredsf.org /Applications/Firefox.app/Contents/MacOS/distribution/bundles/
fi

The if statement above is potentially unnecessary, since it’s unlikely there would be a situation in which Firefox would install but somehow the internal contents of /Contents/MacOS/distribution/bundles/ is preserved, but I figure the extra check won’t hurt.

You can also set this same script to be a postinstall_script for the CCK package, so that if you ever have to add more addons to Firefox, you can guarantee that the symbolic link will be established.

To guarantee the sanctity of our CCK, we’d have to add an installs item to check that the unpacked CCK exists. We check the CCK’s path, and that the CCK’s md5 matches the expected one (so that we can guarantee it hasn’t been changed). The CCK’s existence and its md5 should be installs keys for the CCK itself.  In this case, I do not explicitly call for an installs check on the symlink itself, on the basis that it’s extremely unlikely someone will delete the symbolic link but not Firefox.app.  Unless the user has administrative privilege, they can’t delete either of them anyway.  If your users have administrative privileges, then it doesn’t really make sense to manage Firefox for them.

The installs keys for Firefox:

<key>installs</key>
<array>
 <dict>
  <key>CFBundleIdentifier</key>
  <string>org.mozilla.firefox</string>
  <key>CFBundleName</key>
  <string>Firefox</string>
  <key>CFBundleShortVersionString</key>
  <string>10.0.10</string>
  <key>minosversion</key>
  <string>10.5</string>
  <key>path</key>
  <string>/Applications/Firefox.app</string>
  <key>type</key>
  <string>application</string>
 </dict>
</array>

The installs keys for the CCK package (obviously you’ll need to change your checksum accordingly):

<key>installs</key>
 <array>
 <dict>
 <key>path</key>
 <string>/Library/Application Support/FirefoxCCK/test-sacredsf-cck@extensions.sacredsf.org</string>
 <key>type</key>
 <string>file</string>
 </dict>
 <dict>
 <key>md5checksum</key>
 <string>8c994a5e24ebee8f8227f5d2e37b97dc</string>
 <key>path</key>
 <string>/Library/Application Support/FirefoxCCK/test-sacredsf-cck@extensions.sacredsf.org/cck.config</string>
 <key>type</key>
 <string>file</string>
 </dict>
 </array>

We do it this way to guarantee that the CCK is always linked to the correct place in Firefox, even if Firefox is updated, or installed separately. Since Firefox always creates the symlink as part of its install, we don’t have to worry about it breaking if the user deletes Firefox, or Firefox gets updated to a new version (which won’t have the directories or symlink inside it by default).

The CCK will only get reinstalled if it’s missing from the /Library/Application Support/ folder (or wherever you initially stashed it).

This way, as long as the CCK is listed as an update-for for Firefox, you’ll always guarantee that the correct Firefox management is installed.  The only thing you need to remember to do is copy the postinstall_scripts to each new version of the Firefox and CCK pkginfos (although the CCK pkginfo will need a new checksum if you make changes).

Mass Deployment

Deploying and Managing Google Chrome: The Rough Guide

The following is a post from the most excellent Nick McSpadden. It is very well written and I am proud that it is the first article published on this site using the new submissions page. Looks like it’s time to change the banner from my Notes from the Underground, er, I mean, Field, to just Notes from the Field!

Greetings!

This is a sort of follow-up to my guide on managing Firefox, this time focusing on managing Google Chrome. I’m working on current Chrome version 18 (which just today got updated to 19), and I don’t know for sure how far back this will work, but I think anything higher than v16 properly supports the MCX policies.

The good news about Google Chrome is that it supports MCX! Unlike Firefox, which requires specific and somewhat obtuse procedures for managing it (including depending upon an add-on that is independently maintained by a hard working individual), the most important parts of Chrome management can be done with already-existing MCX controls.

First let me start off with a link to a very helpful set of information: http://www.chromium.org/administrators
That link covers just about everything you’ll need to know about Chrome policies and management, though some of it is buried. I discovered (much to my chagrin) that the Chromium site is much more thoroughly documented that Google’s official “Chrome for Administrators” site.

Some important notes about Chrome MCX: all Chrome policies are required to be set to “Always.” They’re like Profiles from Profile Managers – there’s no middle ground. Even if you set it to “Once” or “Often,” Chrome will treat the policy as permanent and prevent the user from changing it. Any policy being managed by MCX in Chrome will be grayed out to user interaction (and there will be a message in the “Options” window about how some settings are being managed by the administrator). So you’re going to have to “Always” manage these settings whether you like it or not.

The good news is, there’s an alternative, the Master Preferences. The downside is that the Master Preferences is a “once” option, and doesn’t prevent the user from changing it. It’s a good way to provide default settings without restricting the users’ ability to personalize it later on. More on that later.

So, following the Mac Quick Start Guide: (http://www.chromium.org/administrators/mac-quick-start)

1. Inside a fresh copy of Google Chrome is a nice fresh copy of the manifest. Access it here: /Applications/Google Chrome.app/Contents/Resources/com.google.Chrome.manifest/Contents/Resources/com.google.Chrome.manifest

2. Load this manifest into WGM

3. Here’s the full description of all policies in the Chrome manifest: http://www.chromium.org/administrators/policy-list-3

4. There are some particularly important settings that will be relevant to most. Here’s what my plist looks like for a lab computer (no individual users):

  • AutoFillEnabled – False (disables the ability to store autofill information)
  • BookmarkBarEnabled – True (forces the bookmark bar to show up on all tabs, all the time)
  • HideWebStorePromo – True (prevents the web store from trying to sell you things, but does not disable the web store)
  • HomePageIsNewTabPage – False (if you don’t disable this, the homepage will be set to the default Chrome tab page, which opens up the “Most Visited/Apps” switcher)
  • HomepageLocation – URL (even if you set this, if HomePageIsNewTabPage is set to true, this URL gets ignored)
  • PasswordManagerEnabled – False (for lab machines, I don’t want them saving passwords, intentionally or accidentally)
  • RestoreOnStartup – 0 (0 forces it to open the homepage URL on startup)
  • SyncDisabled – True (same reason as Password Manager – I don’t want these personalized at any time).

That gives you a basic setup for most things you’ll need to worry about. If you deploy this, you’ll notice a few problems, though. The first time you launch Chrome, it gives you an undismissable dialogue box asking you if you want to make Chrome the default or submit other info. That’s bad. The above manifest also provides no way to control the auto update mechanism, if that’s something you want to do.

This is where the Master Preferences file comes in – http://www.chromium.org/administrators/configuring-other-preferences. By specifying a Master Preferences file, we can load up default preferences for user accounts *when they are created.* Note that the Master Preferences file has absolutely no effect on already existing Chrome profiles – only upon new-user generation does Chrome load this file. It literally copies and pastes the settings in here into the appropriate places in ~/Library/Application Support/Google/Chrome/Default/Preferences.

On Mac OS X, the Master Preferences file must be located at:
/Library/Google/Google Chrome Master Preferences
(yes, really – the file must be named “Google Chrome Master Preferences” with no extension), and must obviously be readable by any user who can launch Chrome (i.e. use 644 permissions).

The Master Preferences file is a JSON file that can contain any of the preferences normally used by Chrome. If you want the full list of all possible preferences, load up a default Chrome profile and take a look at the Preferences file I mentioned at the path above. It has everything you’d ever want (and a lot of stuff you probably don’t). To save you some time, here are some important ones you’ll want to use specifically for deploying Chrome:

{
"homepage_is_newtabpage" : false,
"browser" : {
"show_home_button" : true,
"check_default_browser" : false
},
"bookmark_bar" : {
"show_on_all_tabs" : true
},
"distribution" : {
"skip_first_run_ui" : true,
"show_welcome_page" : false,
"import_bookmarks" : false,
"import_bookmarks_from_file" : "/Library/Google/chrome_bookmarks.html",
"make_chrome_default" : false
},
"sync_promo" : {
"user_skipped" : true
}
}

The chromium.org page I linked above goes into a bit more detail about this, but I want to give a quick note about the interaction between preferences and MCX. MCX always wins. Any policy managed by the MCX and also specified in the Master Prefs will always go the MCX policy. In the example above, if I had set “homepage_is_newtabpage” to true, it would still be false because MCX sets it to false, and that policy is always enforced.

The really import part is the “distribution” section. “skip_first_run_ui” will get rid of that annoying dialog box that comes up when you first launch Chrome. The “import_bookmarks” option asks the user through a UI dialog box if the user wishes to import bookmarks from another browser. Obviously, we want to suppress that. There’s an option instead to silently import bookmarks from an HTML file. You can create this bookmarks HTML file by setting up the bookmarks the way you want, and then Exporting them in the Bookmark Manager. I place that bookmarks file in /Library/Google/ because it’s already used, but you can put it anywhere. There is, however, a known bug that has now been assigned a milestone and a solver in Chromium’s bug list – the “import_bookmarks_from_file” is actually ignored if the “skip_first_run_ui” is set to true. So right now, you can’t silently import your bookmarks in.

The “sync_promo” item doesn’t seem to be necessary if you disable Sync in the MCX settings above, but since MCX policy always wins over Master Prefs, there’s no penalty or downside to including it.

Note that your JSON syntax has to be perfect for this to work. Any incorrect comma placements, and it simply ignores your master prefs file. If you find that your Master Prefs isn’t loading up as expected, run Chrome from the Terminal with the debug log turned on to see what’s happening:
/Applications/Google Chrome.app/Contents/MacOS/Google Chrome –enable-logging –v=1
This places a file called “chrome_debug.log” in ~/Library/Application Support/Google/Chrome/Default/ (i.e. default user data directory). The first line will tell you exactly what went wrong with your Master Prefs file.

Now, there’s still one more problem here: new tabs open up to the default Chrome “New Apps / Most Visited” switcher page (called the newtab page). Unfortunately for us, there’s no way to change this behavior present in the UI. The good news is, this behavior annoys plenty of other users, and there are a million extensions you can use to get rid of it. More good news, is that you can silently include extensions in your MCX manifest!

So simply add this to your MCX settings above (forgive the pseudo XML here, just to indicate type of key):
<array> <string>lcncmkcnkcdbbanbjakcencbaoegdjlp;https://clients2.google.com/service/update2/crx</string> </array>

This silently forces the install of an extension called “Empty New Tab Page,” and specifies an update URL for it (required, since Chrome autoupdates its extensions too if they come from the Chrome Web Store / Extensions pages). The extension does what you think it does – you get a blank page. There are other extensions for customizing the new tab pages, or anything else, so as long as you get the extension ID (it’s the long block of letters in the beginning), you can load whatever you want in here.

There you go! I’ve tested this using Local MCX on my 10.6 and 10.7 machines, and it works perfectly (deployed through Munki as well). On the whole, Chrome is a bit easier to manage and deploy than Firefox, just because it doesn’t require modifying the app itself to do this. Also, the Master Preferences file works for any instance of Google Chrome – even if the users install a copy somewhere other than /Applications. This also does work for Chromium, the open-source version of Chrome.

Hope this helps someone.

Mass Deployment

Deploying and Managing Firefox: The Rough Guide

Another Great Article Submitted From Nick McSpadden:

After working with this for a bit, I’ve come up with a step by step installation process for Firefox 10 ESR + CCK deployment on Mac OS.

Firefox CCK Guide – Part I
Most of the information about add-ons that you’ll need is in Mike Kaply’s blog:

http://mike.kaply.com/2012/02/09/integrating-add-ons-into-firefox/

1) Install CCK Wizard in Firefox 10 ESR
2) Run and configure CCK Wizard the way you want
3) Save the CCK data into a “CCK” folder anywhere you’d like.  This folder will contain:

  • cck.config
  • cck.xpi
  • xpi/ directory

4) When done, open up CCK/xpi.config
5) Copy the contents of the id=<name> key – this is the name you provided when configuring the CCK addon.  In my example, it is “test-sacredsf-cck@extensions.sacredsf.org”.
6) Rename “xpi” folder into the ID key from Step 5
7) Inside Firefox, create: Firefox.app/Contents/MacOS/distribution/bundles/
8) Move renamed xpi folder from Step 6 into Firefox.app/Contents/MacOS/distribution/bundles/
9) Launch Firefox, enjoy CCK!

Now, this is means that Firefox needs to be specially packaged and distributed during deployment. While this is easy for first-time deployment, it does mean that future versions of Firefox will also require repackaging. If you want to avoid this, it means you’ll have to change Firefox’s addon scopes. If you’re already repackaging Firefox for the CCK as above, then it isn’t a big deal, use the instructions in Mike Kaply’s blog:

http://mike.kaply.com/2012/02/21/understanding-add-on-scopes/

Firefox Changing Add-On Scopes – Part II
1) Make a text file named whatever you want as long as it ends in .js, such as “scopes.js”
2) Add these two lines to the file:

pref("extensions.autoDisableScopes", 0);
pref("extensions.enableScopes", 15);

3) This file needs to be saved in Firefox.app/Contents/MacOS/defaults/pref/ (the blog suggests it should be defaults/preferences/, but for me /prefs/ was already created)

4) Now user scopes are changed to the settings above.

However, if you want to avoid repackaging Firefox completely every time an update or a change to your CCK configuration comes out, or you want to have different CCK settings for each user on the system, you’ll need to change things up a bit. One way or the other, you’ll need to change the Addon Scopes, because FF10′s defaults lock out the extra directories. If you don’t want to rebundle/repackage Firefox 10, you can use any script to add in the preferences you need into Firefox.app. You can do it simply with echo:

$ echo -e "pref("extensions.autoDisableScopes", 0);npref("extensions.enableScopes", 15);" > /Applications/Firefox.app/Contents/MacOS/defaults/pref/scopes.js

(obviously double check to make sure the .js file can be read by Firefox, although I didn’t have to do anything for it to work)

Doing this allows Firefox to use any of its valid locations for extensions, listed here:

https://developer.mozilla.org/en/Installing_extensions

In other words, you’ll want to move and rename the “xpi” folder from the CCK Guide Step 6 into this location if you want it to affect all users:

/Library/Application Support/Mozilla/Extensions/{ec8030f7-c20a-464f-9b0e-13a3a9e97384}/test-sacredsf-cck@extensions.sacredsf.org

This unpacked folder (from CCK Guide Step 4) contains the xpi contents:

  • plugins/
  • modules/
  • install.rdf
  • defaults/
  • components/
  • chrome.manifest
  • chrome
  • cck.config

…and so forth.

Use this location if you want it to affect individual users only:
~/Library/Application Support/Mozilla/Extensions/{ec8030f7-c20a-464f-9b0e-13a3a9e97384}/
(i.e. /Users/…/Library/…)

To summarize:

I. For an individual user, I’d need to change Firefox’s addon scopes, and I’d need the unpacked xpi contents located here:
~/Library/Application Support/Mozilla/Extensions/{ec8030f7-c20a-464f-9b0e-13a3a9e97384}/

II. For all users, but not packaged within the application itself, I’d need to change Firefox’s addon scopes, and put the unpacked xpi contents here:
/Library/Application Support/Mozilla/Extensions/{ec8030f7-c20a-464f-9b0e-13a3a9e97384}/

III. For all users, who will be unable to disable or even see the add-on, inside the Firefox.app bundle itself, I don’t need to change addon scopes. I just need to put the unpacked xpi contents here:
/Applications/Firefox.app/Contents/MacOS/distribution/bundles/{ec8030f7-c20a-464f-9b0e-13a3a9e97384}/

That’s how you get the CCK configured and installed in its various permutations on Mac OS X. I hope that helps anyone who was struggling or thinking about adopting the Firefox 10 Extended release into their deployment strategy, as the CCK is a great tool for preconfiguring Firefox to suit your enterprise’s needs.

“But wait!” you might say.  “How do I perform an enterprise-level deployment with this method?”  See my post here for details on incorporating this into Munki: http://krypted.com/mass-deployment/deploying-and-managing-firefox-part-2-working-with-munki/.

iPhone Mac OS X Mac OS X Server

Apple Configurator 1.0.1 Released

Apple has released version 1.0.1 of the Apple Configurator tool. To install the first update to Apple’s new tool, go to the App Store on a computer that has Apple Configurator installed, click on Updates and then click on the Update button for Apple Configurator.

The update has a number of new features and fixes. The first is that Enterprise Apps can be installed. Previously, when you went to install internally developed applications, you would get an error that the installation could not proceed. Another great fix is that commas are now escaped when importing application codes from the VPP spreadsheets (a comma in a CSV/comma separated value would kill the ability to import VPP codes before). Another fix is to let you pull redemption codes from unsupervised device (this makes me very happy).

The redemption codes that you buy an app with can also now be used in Configurator, according to the release notes. This worked for me anyway, but I’ve read reports that people had to burn an additional code to use them with Configurator. The remaining redemption codes are now listed properly, as well. Another fix is that Notes and Bookmarks pushed into iBooks and iTunes U are restored properly when supervising devices. The WPA2 passwords had been wonky (according to the content of that payload), so that’s been fixed as well.

Also, a bug I hadn’t noticed, the capacity of an 8GB iPod Touch is now displaying properly…

iPhone Mac OS X Mac OS X Server Mac Security Mass Deployment

Managing iOS Devices with Apple Configurator

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 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.

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/com.apple.configurator/Resources. 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/com.apple.configurator/IPSWs 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!