Apple Updates Notarization Requirements

Notarization is a big topic amongst Mac Admins, as we start to prepare to release macOS 10.15 Catalina to our fleets. Distributing tools, and allowing users to setup their own environments, is a huge part of the Mac Admin life. Today, Apple released some new guidance concerning the requirements for notarization of software packages.

To make this transition easier and to protect users on macOS Catalina who continue to use older versions of software, we’ve adjusted the notarization prerequisites until January 2020.

You can now notarize Mac software that:
• Doesn’t have the Hardened Runtime capability enabled.
• Has components not signed with your Developer ID.
• Doesn’t include a secure timestamp with your code-signing signature.
• Was built with an older SDK.
• Includes the entitlement with the value set to any variation of true.

Make sure to submit all versions of your software. While Xcode 10 or later is still required to submit, you don’t need to rebuild or re-sign your software before submission.

Apple Developer News

This represents a substantial change over the existing guidelines. This is a positive development, in my eyes, which allows more developers to submit their packages, disk images and zip files for notarization in their current form, and to work over a longer term to get the Hardened Runtime enabled, as well as find replacements for third-party pre-compiled frameworks that are submitted with another developer’s signature embedded.

This does still mean you need to get notarized packages, zips and disk images for your environment if you intend to have 3rd party non-AppStorer software installed directly by end users. If you are installing tools via Munki’s LaunchDaemons or Jamf’s framework, this doesn’t apply yet.

Like the Return of an Old Friend: NetNewsWire 5.0

In the early days of Web 2.0, in the short time after the dot com crash, there arose a common standard for syndicating your blog across the web, into RSS Readers. Google Reader was a big damn deal in those days, but before Google Reader hit the market, there was NetNewsWire.

Brent Simmons’ app was the RSS Reader for the Mac for a good long time, and an app that I lived and died by. In the days where Twitter (blessedly) did not yet exist, getting your news meant going to a website manually, like some kind of animal. NetNewsWire could read the secret code that held these sites together and produce a feed of articles that you could pay attention to directly, without having to remember which sites you needed to see.

In the post-social world, where suddenly everything got dumped out to the feeds full of our friends’ quick thoughts and longer form rants, RSS began to die a bit. Google saw that Reader was cannibalizing their own ads, and rapidly pushed it to the ash-heap of history, and in-so-doing, wrecked a whole lot of models for publishing. Suddenly, we were back to depending on people to go to browser-based reading habits, which came with a ton of terrible ads, tracking that was just full of garbage, or a social existence defined by the hellscape that Twitter and Facebook have become.

All this set the table for the return of NetNewsWire, which exited beta last week, and returned to my dock shortly thereafter. The base metaphor of NetNewsWire (NNW) is unchanged: feeds, grouped according to your choices, contain stories, which can view feed by feed, or in a timeline. Anything that can be served up as RSS can be shunted over into NNW’s hopper to await your attention.

For the last few years, I have used the #blog-feed channel on the Mac Admins Slack as my version of a professional RSS reader. I’m moving all those feeds to NetNewsWire so I can better track what I’ve read and what I haven’t. Now I’ve got a great view into what I’m up to date on, and what I’m yet to cover.

A view into my RSS feeds

This is about to be heavy season for Mac Admins, if it’s not already. We’re in the waning days of the beta period before macOS Catalina 10.15 drops and iOS 13 is released. We’ve got a lot of work ahead of us. How about helping yourself with a whole list of helpful feeds that are there to keep you up to date?

Enter the Mac Admin Blogs OPML Repo.

Download the OPML File, Open NetNewsWire, File > Import Subscriptions.

And there ya go!

The repo is public on Github, so feel free to contribute those blogs I missed.

And congratulations, Brent Simmons! NNW 5.0 is a return to RSS for me, and I couldn’t be more excited to be reading more from my friends.

Notarization Follow-Up and Video

The Loyal Order of the Notaries

This summer, I gave a talk at the Mac Admins Conference at Penn State, focused on Notarization, called The Loyal Order of Notaries. It was a lot of work to put together the talk, and I spent more time on it than I have any talk I’ve ever given. I am proud of the work, but there’s a problem.

I Got Something Very Wrong

46 minutes into the talk I said: “this is good news: whitelisting the Team ID affects the notarization restriction.”

This is not correct.

Whitelisting the Team ID in a Kernel Extensions payload from a User-Accepted MDM does not affect the notarization requirements in the Catalina betas at this time. What I said in the talk was based on my conversations with colleagues and friends, and an conversation I’d had with a member of Apple’s staff, and on my initial results with the first beta of Catalina.

My conclusions were based on the question I asked in that inteview: Will there be a way to whitelist Developer IDs for notarization the same way there is for Kernel Extension loading? The answer was an unequivocal yes.

I assumed that the method for this was the same payload. That has turned out not to be the case in my testing thus far.

So What Now?

I don’t know.

That’s not a very satisfying answer, I recognize. I wish I had a better one.

Here’s what I do know: merely providing a kernel extensions whitelisting of the Team ID of a Developer is insufficient to prevent warnings for packages and disk images signed with that Developer Certificate.

I feel like I blew it.

I had tested this with my Catalina machine, but I realized that the package I was testing with was signed, and with a Developer ID I’d whitelisted, but it wasn’t a unique path or package. I had already installed that package once before, before I’d whitelisted the Developer ID. The LaunchServices Database had a record of the package and the path from where it had come from. It had already exited quarantine, and thus wasn’t passing through the Gatekeeper checks that the talk described, despite having been uninstalled.

How Do I Deal With Non-Notarized Materials?

Catalina’s requirements for notarization on signed packages, signed disk images and unsigned zip files are enforced by Gatekeeper processes, which depend on file quarantine flags. If a package, disk image or zip file arrives via browser download, USB file transfer, or AirDrop transaction, it comes with a quarantine flag. Escaping quarantine means passing a notarization check (online or offline), and a code-signing check, and a check for malicious code as defined by MRT and XProtect.

Or, you can deliver the payload through a non-quarantine method, like curl, or the jamf binary.

These methods are not quarantine aware, and while they do carry some additional ACLs, they do not appear to prevent the installation of packages by Apple-signed Installer, or mount of the image by Apple-signed Disk Utility. That means that tools like Munki or Jamf can continue to deploy software that is not notarized to enterprise machines.

One other consequence of these changes is that it’s not just packages software programs that are affected. During testing, I found a package that is properly signed that delivers Motion and Final Cut Pro templates that also triggered the quarantine warning. They were signed for distribution, but not notarized. They still flagged the quarantine check because they were distributing files. I packaged a sent of fonts for delivery to /Library/Fonts, signed the package, uploaded it to Slack for a colleague to test, and sure enough, quarantined:

If you’re planning for your co-workers to be able to open packages, zip files or disk images that aren’t notarized, you’re going to need to prepare them to right-click on the file, click Open, and then accept the warning that follows.

This isn’t ideal.

This will mean that anything you intend to deliver to Catalina computers will need to either arrive without a Quarantine flag, or be installed by a tool that can receive updates without a Quarantine flag and install them directly.

I apologize to the folks in the room at Penn State, to the organizers of the Mac Admins conference, and to anybody who will see the video. I got it wrong. But I’ll own what’s mine, and we’ll learn more together in the future.

Go For The Moon

Last night, we braved the crowds and the heat to go down to watch Go For The Moon, a multimedia spectacular in front of the Smithsonian Castle. The experience was like nothing I’ve ever seen, or could imagine. Using the Washington Monument as a canvas, along with a pair of split screens framing the obelisk, the incredible team at the National Air & Space Museum and 59 Productions made magic.

Projecting a life-sized Saturn V rocket launch on the Washington Monument, and eventually the arrival of Eagle on the Moon, along with the Rice University speech and the achievement of the Apollo programs, the audience is left to sit in awe for 17 minutes as the video plays out. The score, by Jeff Beal, provides additional encouragement.

The Rice University speech, famous for it’s “We choose to go to the Moon… because it will be hard” also has an incredible section on ethical leadership in technological pursuits:

“For space science, like nuclear science and all technology, has no conscience of its own. Whether it will become a force for good or ill depends on man, and only if the United States occupies a position of pre-eminence can we help decide whether this new ocean will be a sea of peace or a new terrifying theater of war. I do not say the we should or will go unprotected against the hostile misuse of space any more than we go unprotected against the hostile use of land or sea, but I do say that space can be explored and mastered without feeding the fires of war, without repeating the mistakes that man has made in extending his writ around this globe of ours.”

Pres. John F. Kennedy, Rice University, September 12, 1962.

President Kennedy said what so many miss: the application of science and technology has no direct conscience of its own, but rather it is the product of people, in their designs, intents, applications, choices, audiences, marketing, and execution of it. The parallels between the strife of the 1960s and the 2010s was clear last night down on the Mall. We were reminded that Apollo happened amid the unjust Vietnam War, amid the unjust fight against the Civil Rights Act, amid the countercultural rebellion against post-war norms.

“We came in peace for all mankind,” reads the plaque on the leg of Eagle, where it remains today. We are capable of doing incredible things as a nation, and NASA is the embodiment of those goals of exploration, of science, of application of technology. It’s just a part of the funding of science that we do as a nation, as part of our pursuit of the future. We need to do more science, not less. We need to do more exploring, not less.

We need the next velcro, the next teflon, the next LED bulb, the next micro computer, and programs like NASA’s Apollo can build those things, in concert with the National Science Foundation. We can do incredible things when we make science and technology into public goods. Engineering and exploration in the pursuit of the furtherance of humanity is a worthy goal for us all.

And we need it now, more than ever.

We took Charlie with us, last night, to see the rocket go up. We’ve been watching From The Earth To The Moon this week, and I know while he was with my parents they talked a lot about the original moon landing in 1969. Like his father, and his grandfather, he thrust his fist in the air as the rocket went up.

I’m sure there are those who see the rocket programs and exploration of space as secondary or tertiary to the other problems of our present. I can understand that. But what will save our planet in the next century is science. It’s certainly not sticking our head in the sand and hoping for divine intervention that isn’t coming. We have to participate in our own rescue. As we bake in record heat — more of a braise, here in DC this weekend — it’s more and more clear that our climate is changing, and with it our future habitability. Kim Stanley Robinson’s science fiction novels of the last decade are fairly bleak and fairly clear: if we’re getting through this, we’re doing it here, not living anywhere else. I think he’s got a point.

If there’s an Apollo program for Charlie’s generation, it may not be about Mars, or the Moon, or Titan or Enceladus. It might be here. But we have to keep going, keep pressing the boundaries of human space, pressing what we’re capable of.

In 50 years, I plan to be back out on the Mall with him for Apollo 100, helping him remember what came before, and what we have yet to accomplish.

Slide from talk, titled The Loyal Order of Notaries

Mac Admins Talk: The Loyal Order of Notaries

The Notarization of binaries with Apple Notary Service is a fascinating topic worth exploring, and in this year’s talk at Mac Admins, I delved deep into the subject. The current version of macOS now requires all kernel extensions not just to be signed by their authors, but to be notarized by the Apple Notary Service. Beginning with macOS 10.15 Catalina, all software will need to be notarized, as well.

This represents a bit of a change over the past, and it will require software developers not just to submit their software for notarization, but to staple the resultant ticket to their binary. Doing this isn’t terribly complicated, but why does this have to happen? What’s the mechanism for getting something notarized? How can we work around this, if circumstances require it?

This post is designed to be both the repository for the slides from this talk, as well as useful links and documentation associated with the materials discussed in the talk. I will not be including my presenters notes.


Please read this important follow-up before reading the resources that follow.

Slides & Downloads

Here are the slides associated with the talk.

Download (PDF)

Online Resources

Apple: Safely open apps on your Mac, a Gatekeeper Guide
Apple: Your Apps and the Future of macOS Security, a WWDC Video from 2018
Apple: Advances in macOS Security, a WWDC Video from 2019
Howard Oakley: Notarization Category on Eclectic Light, a collection of blog posts on notarization
Apple, Gatekeeper and Developer ID, a WWDC transcript from 2012
Rich Trouton: Clearing the quarantine extended attribute, a blog post on xattr and quarantine bits.
Howard Oakley: More about the quarantine extended attribute, a blog post on xattr and quarantine bits.
Mothers Ruin: Suspicious Package, a tool for reviewing packages and apps

Thank Yous

My sincerest thanks to #notarization on the Mac Admins Slack, to people like Joel Rennich, Robert Hammen, Rich Trouton, Armin Briegel, Jennifer Unger, Dr. Emily Kausalik-Whittle, Some Little Birdies, and anyone else I inflicted my questions and draft slides on. I also want to thank Apple for their wealth of new documentation tools, and the WWDC video archives.

Tom Bridge standing in front of Harbour Bridge and Sydney Opera House

Wrap-Up Documentation from the Fundamentals of Wi-Fi: Physics Always Wins

I’m incredibly grateful to AUC and Tony Gray for their invitation to Chris Dawe and I to present our workshop, Fundamentals of Wi-Fi: Physics Always Wins. While we’re not making our full slides available for this talk, we did want to provide some external-facing documentation for our talk that gives you some of the key materials that we used while making this talk.

How to Reach Us

Tom Bridge
Slack: tbridge
Github: tbridge

Chris Dawe
Slack: ctdawe

Books & Printed Material

Sometimes, you need to start with printed materials.

CWNA 107 Study Guide

The Wireless LAN Professionals organization is the certifying authority for professional WLAN Engineers, and their mission includes training and certification. the CWNA 107 Study Guide (and the now discontinued Sybex volume for the 106 exam that preceded it) is an excellent resource to understanding much of the Wireless sphere.

Online Resources

General References:

WLAN Pros Resources Page (Includes WLPC Sessions)

Certified Wireless Network Professionals

The home of vendor-independent technical certification for Wi-Fi

Revolution Wi-Fi

Andrew von Nagy’s site is home to comprehensive discussion and analysis of developments in Wi-Fi technology. Andrew is also the creator of a Capacity Planning tool that will provide guidance on access point needs based on a description of your fleet.

Capacity Planning Worksheet

Section 1: Wi-Fi and Radio Basics

Attenuation Values for Common Building Materials

History of 802.11 Specification, Justin Berg, George Mason University

Hedy Lamarr and George Antheil’s Patents

When George Antheil Met Hedy Lamarr

How OFDM Subcarriers Work

This piece was what unlocked the importance of OFDM to Wireless connectivity. Learning how it changed Wi-Fi forever helped me understand its importance.

Best 802.11ac Channel Map Ever

Choosing 802.11ac Channels in Australia

Rules of Tens and Threes

802.11ax Brings OFDMA

802.11 Alphabet Soup

Wi-Fi Certified 6

Section 2: Wi-Fi Basic Operations

Understanding 802.11 Management Frames

Explaining the Concept of a TXOP

Modulation & Coding Scheme Lookup Table

Section 3: Network Design

Aerohive High-Density Design Guide

The Dreaded Dragonfly

Mike Albano’s Client Capabilities List

BYO AP on a Stick Kit

Understanding WLAN Capacity, Darrel Derosia, WLPC Phoenix 2017

Watch this video to gain a greater understanding what turns out to be a vast gulf between vendor hardware performance specs and real-world scenarios with a mixed client base.

Divergent Dynamics: Wi-Fi Design and Deployment Methodology

Understanding Airtime Utilization

Section 4: Apple-specific Design Concerns

Apple Deployment Documentation (Appendixes include WiFi Specs for iOS and macOS Devices)
iOS Deployment Guide
macOS Deployment Guide

Apple’s two deployment guides supply Apple’s general recommendations for Wi-Fi networks (which aren’t too far from ours, generally), as well as Wi-Fi specs for Apple’s devices. Oddly, the iPad specs list is currently badly broken.

Enterprise Best Practices for iOS Devices and Mac Computers on Cisco Wireless LAN

Apple Roaming Documents
Apple TechNote: macOS Roaming
Apple TechNote: iOS Roaming

Advanced Roaming Technologies for iOS (discusses 802.11k, 802.11r, and 802.11v and their utility in roaming)

Section 5: Tools & Software

Wi-Fi Explorer (Lite, Regular, Pro)

Wi-Fi Signal




Metageek Channelyzer & Wi-Spy DBx

Ekahau Pro & Ekahau Cloud

Tamograph Site Survey

Section 6: Security

Podcast: Understanding the 4-way Handshake

David Acland’s Talk on Certificates, Signing and Hashes

KRACK Attacks

Analysis of SAE and WPA3

802.1X and EAP Types

10.12.5 and SHA-1 Certs

Waving the Green Flag

I love this time of year. This is where the rubber meets the road for people who manage Macs and iOS devices. Apple’s Worldwide Developer Conference is going on in San Jose, after a kickoff yesterday with a banner keynote and a fascinating state of the union.

Last night, we talked about this in a Flashcast Episode of the Mac Admins Podcast:

This is open season for engineering. This is where I find immense satisfaction in my chosen profession. We have so much to do between now and the release of macOS 10.15 Catalina in the Fall, and there’s a lot that we’re going to have to deal with between now and then. Here’s what my questions are, right now:

  1. What is the practical effect of a read-only system container from the Admin’s perspective? This appears to be a fully-abstracted development in the security story, and that represents a huge win for the security of the platform.
  2. What are the ramifications of modern authentication methods for automated device enrollment? Is this a place where, once we’ve performed a successful authentication, we can use what’s returned from the OIDC endpoint to generate a user account?
  3. What all do I need to know about the deprecation of bash and other scripting tools included with the OS as default? Most organizations are already pushing their own toolchain, how’s this fit into the picture?
  4. What does the gating of fdesetup behind PPPC-style controls mean for things like Crypt?
  5. How are the new Device Management controls going to be used in real-world situations?

There’s a lot more to think about as we get into sessions this week. I’m excited. This appears to be a huge win for the Mac Admins community, and there’s so much in here that I’m excited to get rolling. While I won’t be upgrading my daily driver to Catalina for a bit (it’s okay to laugh at me, I’ll probably be upgraded by Friday), I am looking forward to setting up the lab and getting deep into the guts of the new security and device management features.

As much as things can be broken during development releases, and feature choices can feel like frustration in the moment, as beautifully-crafted workflows that represent the culmination of effort and intention fall apart, this is where the work begins anew. We get new tools. Better tools. I can’t look at System Extensions and the new security endpoint protection frameworks and not see the possbilities.

At times like this, we get to invent our own future.

Let’s get to it, shall we?