Home > Jamf Pro, Mac administration, macOS, Scripting, Secure Token, Security > Mad, bad and possibly dangerous – a cautionary tale of software installation

Mad, bad and possibly dangerous – a cautionary tale of software installation

In my career, I’ve run across a lot of terrible installers in a variety of forms. The one I ran across today though is noteworthy enough that I want to point it out because of the following reasons:

  1. It’s an installer application. I have opinions on those.
  2. It’s for a security product where, as part of the installation, you need to provide the username and password for an account on the Mac which has:
    • Administrator privileges
    • Secure Token

Note: I have no interest in talking to the vendor’s legal department, so I will not be identifying the vendor or product by name in this post. Instead, I will refer to the product and vendor in this post as “ComputerBoat” and leave discovery of the company’s identity to interested researchers.

For more details, please see below the jump.

To install ComputerBoat, you will need the following:

  1. The ComputerBoat installer application.
  2. A configuration file for the ComputerBoat software.
  3. The username and password of an account with the following characteristics:
    • Administrator privileges
    • Secure Token

Once you have those, you can run the following command to install ComputerBoat:

Why it necessary to provide the username and password of an account with admin and secure token? So this product can set up its own account with admin privileges and a Secure Token!

Why is it necessary for this product to set up its own account with admin privileges and a Secure Token? I have no idea. Even if it is absolutely necessary for that service account to exist, there is no sane reason why an application’s service account needs a Secure Token. In my opinion, there are only three reasons why a service account may need to have Secure Token.

  1. To add the service account to the list of FileVault-enabled users.
  2. To enable the service account to create other accounts which have Secure Tokens themselves.
  3. To enable the service account to rotate FileVault recovery keys.

All of those reasons have serious security implications. Even more serious security implications are brought up by the fact that this vendor thought requesting the username and password of an account with admin and secure token was an acceptable part of an installation workflow. To further illustrate this, here’s a sample script which the vendor provided for installation using Jamf Pro:

Here, the installation workflow is as follows:

  1. Use curl to download a compressed copy of the ComputerBoat installer’s configuration file in .zip format.
  2. Use ditto to unzip the dowloaded configuration file into a defined location on your Mac.
  3. Use ditto to unzip the downloaded installer into the same defined location on this Mac.
  4. Run a directory listing of the defined location.
  5. Remove extended attributes from the uncompressed ComputerBoat installer application.
  6. Using credentials for an admin account with Secure Token, install the ComputerBoat software and set up a new account with a Secure Token to act as the application’s service account.
  7. Checks to see if it can run a command to get the newly-installed application’s version number.
    • A. If the version number comes back, the install succeeded. 
    • B. If nothing comes back, the installation is reported as having failed.

The only defense I can think of for the vendor is that it says “Sample” in the description. That may imply that the vendor built this as a proof of concept and may be trying to subtly encourage their customer base to develop better solutions for deploying the ComputerBoat software on Macs. On the other hand, I received this script on the customer end of the transaction. That meant that someone at the vendor thought this was good enough to give to a customer. Either way, it’s not a good look.

Why is this script problematic?

Security problems

  1. You need to supply the username and password on an account on the Mac with admin privileges and Secure Token using a method that other processes on the computer can read. This leaves open the possibility that a malicious process will see and steal that username and password for its own ends.
  2. The script is set to run in debug mode, thanks to the set -x setting near the top of the script. While this may be helpful in figuring out why the installation process isn’t working, the verbose output provided by debug mode will include the username and password of the account on the Mac with admin privileges and Secure Token.


Installation problems

1. Without supplying the username and password on an account on the Mac with admin privileges and Secure Token, the installation process does not work.

If you’re deploying this security application to your fleet of Macs, that means that the vendor has made the following assumptions:

  • You have an account with admin privileges and Secure Token on all of your Macs which share the same username and password.
  • You’re OK with providing these credentials in plaintext, either embedded in the script or provided by a Jamf Pro script parameter in a policy.

2. Without providing a separate server to host the ComputerBoat installer’s configuration file, the installation process does not work.

  • If you’re deploying this software, the vendor apparently did not think of using Jamf Pro itself as the delivery mechanism for this configuration file. Hopefully you’ve got a separate web server or online file service which allows for anonymous downloading of a file via curl.

3. Without figuring out a way to get the installer into the same location as the downloaded configuration file, the installation process does not work.

  • Overlooked by the installation script is this question: How does the installer get to the location defined in the script as $COMPUTERBOATEPM_INSTALL_TMP ? The script assumes it’ll be there without including any actions to get it there or checking that it is there.

There are further issues with this script, but they fall into the category of quirks rather than actual problems. For example, I can’t figure out the purpose of the following lines:

xattr -d $COMPUTERBOATEPM_INSTALL_TMP/Install\ ComputerBoat\ EPM.app

Neither command seems to do something useful. The first one will list the contents of the directory with the configuration file and the installer application, but then that information isn’t captured or used anywhere. The second removes extended attributes from the ComputerBoat installer application, but the reason for this removal isn’t explained in any way.

You can draw conclusions about a vendor and their product quality by looking at how that vendor makes it possible to install their product. In examining this installation process, especially considering this is for a product intended to improve security in some way, I have drawn the following conclusions:

  1. The vendor has not invested resources in building macOS development or deployment expertise.
  2. The vendor is unwilling or unable to avoid compromising your security with their product’s installation process.
  3. The vendor is not serious about developing or maintaining a quality product for macOS.

When you see installation practices like this, I recommend that you draw your own conclusions on whether this is a vendor or a product you should be using.

  1. June 5, 2020 at 9:58 pm

    all cyber professionals out there that develop installers like this should be put on an ark and left to float in middle of the pacific ocean until the come back with a proper package.

    • Brian Martin
      June 5, 2020 at 10:10 pm


    • June 6, 2020 at 11:13 pm

      There are a lot of security tools that have been “ported over” to the macOS platform, that don’t adhere to Apple’s security guidelines. Why? Because they want to circumvent it all. Oh, and they want to make money, hence the “We support macOS, didn’t you notice we have a bullet item on our marketing material?” Many of these third party existing security tools are still struggling to support 10.15 (with 2-3 months before the release of macOS 10.16). Companies that care about security would do well to *vet* these security tools on macOS instead of blindly agreeing to purchase it because a box was checked on its website.

  2. June 5, 2020 at 10:02 pm

    Thanks for the great article. Articulates to a “T” why I despise deploying this software. Already forwarded along to 5 IT directors I work with.

  3. June 5, 2020 at 10:09 pm

    Thanks for the examination and write-up, der flounder. I must ask: Who doesn’t love a good cybersecurity product that, by installation, diminishes the security of your whole endpoint fleet?

    One would think these peddlers of security snake oil would be all the wiser, however, repeat observation of credential and authentication mishandling for MacOS deployments demonstrates widespread industry negligence.

    Hopefully as time ticks on we will continue to see a growing intersection with  macOS and enterprise security engineering expertise. Sadly though, the burden of building that sort of fusion falls onto the shoulders of the client engineer who reports it. I don’t blame you for not wanting to contact them. Hopefully you can cancel the contract, but too often, that won’t fly either. The client is stuck with the bill, and another piece of dusty “shelfware”.

    On the bright side, if the organization that produced the product also participates in a bug bounty program, you could make some cash for demonstrating exploitation of the misconfiguration. A list of public participating companies is hosted here:


  4. Brian Martin
    June 5, 2020 at 10:10 pm

    You have me beat on problematic Mac software installations this week. I think I know which product you’re talking about based on the clues and simple Googling. I have never used that product myself.

    My annoying one is a certain statistical analysis package by a certain large vendor that we both know of well. It uses an installanywhere application and requires some tomfoolery to get properly installed in Catalina.

  5. June 5, 2020 at 10:37 pm

    Deleting the extended attributes gets rid of any quarantine attributes. That’s the only reason I ever mess with extended attributes.

    There’s a website ComputerBoat.

  6. hkabik
    June 10, 2020 at 3:51 pm

    Their explanation for why they did this is pretty laughable per the ticket we created. They claim that they are working on a new installer to split off this “feature”.

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