VMware VCNS/NSX Edge Gateway SSLVPN and El Capitan 10.11.1

It is sad that most of my blog posts are related to an SSLVPN client and not my area of expertise, storage.  The previous SSLVPN client post is by far the most popular post on my blog, so here is to another post that will hopefully help someone.  My previous post on the SSLVPN client can be found here.

I had previously been running the NAclient from Edge version 6.1.3 on OS X 10.11 without issue, however the installation will no longer work due to security controls put into place by Apple.  There is a trend here, the previous problem with getting the NAclient installed onto OS X 10.10 (Yosemite) was also due to failure to meet Apple security guidelines, they didn’t implement code signing (amongst using deprecated methods of configuring/starting services).

If you attempt to install the NAclient on a current version of Apple OS X 10.11.1 you will see a lovely error like this one:  “This package is incompatible with this version of OS X and may fail to install.”


And if you select to Install Anyway it will just fail with the error: “The installation failed.  The installer encountered an error that cause the installation to fail.  Contact the software manufacturer for assistance.”Install_VMware_SSL_VPN-Plus_Client_Installer

It took some digging to figure out what is going on, and I used one of my favorite tools (Pacifist) to open the actual installer package to see where the installation files are written.


I also remember reading about Apple’s System Integrity Protection locking down access to secure system file locations, including /usr, /System, and others.

In researching this I found Apple’s developer guidelines for System Integrity Protection, and it clearly states that /usr is off limits.


Source: Apple System Integrity Protection Guide

Now that the root problem is found, I sought a work around.  Previously we had to disable the check for kext signing, though that didn’t permanently solve the issue because the dependent services wouldn’t work after reboot due to use of deprecated methods.  This time I was able to find that you can manage the System Integrity Protection using the command csrutil:


In order to manage System Integrity Protection you must reboot your system into Recovery Mode, you can do this by holding down Command+R on system startup.  You should boot to a OS X Utilities menu.  Click Utilities and select to open Terminal.

Within terminal you simply need to run ‘csrutil disable’ and then reboot the system, the easiest way to do this is with a single command line of ‘csrutil disable; reboot’.


Once the system is booted up you can  now successfully install the NAclient, test that it works.  At this point you can repeat the process and run ‘csrutil enable; reboot’ to turn System Integrity Protection back on…which I strongly encourage.  It is disappointing that we have to disable security controls to install a security tool, however at least we only have to have it disabled upon install.  Any actual package upgrades would require you to repeat this process, but lets face it…VMware hasn’t released an update to this client since the last time I reported a bug in it 😉

Happy VPN’ing.

—– Follow up 11/24/2015 —-

It is becoming obvious that VMware doesn’t take client support for SSLVPN seriously, I will be investigating options to migrate our environments off of SSLVPN within the Edge Gateway.  It is entirely idiotic that you must deploy an entire new version (that isn’t even released yet) in order to fix a simple client installer bug.  That means you have to wait for the new version of the NSX stack to be qualified and supported by GSS with any of your other software components (e.g. vCloud Director), which isn’t an immediate process.  This leaves customers exposed for a long period of time, it increases operational burden for support teams and in general is a horrible way of delivering client software.

Client software should be released and maintained independently of the entire NSX Manager/Edge Gateway bundle.  Requiring every customer to do a massive upgrade of their entire environment just to fix a bug (that they should have known about months ago and should have been included in a 6.1.x release!) in client software is not acceptable.

— Edit 11/30/2015 —

An additional challenge here is if you disable the work around (have System Integrity Protection enabled), as you should, it will result in the client breaking if you run an installer again (say to add another VPN profile).  If you need to add another VPN destination you really should just edit the config file /opt/sslvpn-plus/naclient/naclient.conf directly with the editor of your choice.

— Update 12/16/2015 —

The work around allows the naclient to function on OS X 10.11.2 as well.  If you have the client installed prior to installing 10.11.2 update it will remain working, the work around will also preserve the ability to install after 10.11.2.

VMware vCloud Network & Security Edge – SSLVPN and Mountain Lion Troubles

October 12 2016 Update – Yosemite & El Capitan:

Wow, its been 3 years since posting this thing and it still gets quite a few hits.  The problem did get worse with Yosemite due to required code signing, however VMware corrected the problem with the naclient that was bundled in NSX 6.1.3.  If you have the naclient installed before upgrading to El Capitan it also works, in my limited testing.  I have heard that trying to install it on El Capitan may encounter issues due to a similar version table as noted below, I have not had a chance to test it on clean install and only tested for Yosemite to El Capitan upgrades.



The addition of client oriented VPN to the vCNS “Edge” (formerly vShield Edge) is a big win, however anyone that attempts to use the product on the current shipping version of Mac OS X will find that it fails to install.  We are using the SSLVPN heavily for a project and encountered this, I decided to dig into the details.

Within the OSX system logs you will find lots of useless errors, ultimately you want to get to the installer errors themselves.  If you open Console.app and look at the /var/log/install.log (or do so from CLI) you will see this error:

installd[4110]: PackageKit: —– Begin install —–
installd[4110]: PackageKit: request=PKInstallRequest <1 packages, destination=/>
installd[4110]: PackageKit: packages=(
“PKJaguarPackage <file://localhost/Volumes/BigFast/Downloads/naclient.pkg>”
installd[4110]: PackageKit: Extracting file://localhost/Volumes/BigFast/Downloads/naclient.pkg (destination=/var/folders/zz/zyxvpxvq6csfxvn_n0000000000000/Cleanup At Startup/PKInstallSandboxManager/1.sandbox/Root, uid=0)
installd[4110]: PackageKit: prevent user idle system sleep
installd[4110]: PackageKit: suspending backupd
installd[4110]: PackageKit: opt/sslvpn-plus/naclient/naclient.app relocated to Applications/naclient.app
installd[4110]: PackageKit: Executing script “./preinstall” in /Volumes/BigFast/Downloads/naclient.pkg/Contents/Resources
install_monitor[4115]: Temporarily excluding: /Applications, /Library, /System, /bin, /private, /sbin, /usr
install_monitor[4115]: Re-included: /Applications, /Library, /System, /bin, /private, /sbin, /usr
installd[4110]: PackageKit: releasing backupd
installd[4110]: PackageKit: allow user idle system sleep
installd[4110]: PackageKit: Install Failed: Error Domain=PKInstallErrorDomain Code=112 “An error occurred while running scripts from the package “naclient.pkg”.” UserInfo=0x7fc30b425a80 {NSFilePath=./preinstall, NSURL=file://localhost/Volumes/BigFast/Downloads/naclient.pkg, PKInstallPackageIdentifier=com.vmware.sslvpn, NSLocalizedDescription=An error occurred while running scripts from the package “naclient.pkg”.} {
NSFilePath = “./preinstall”;
NSLocalizedDescription = “An error occurred while running scripts from the package \U201cnaclient.pkg\U201d.”;
NSURL = “file://localhost/Volumes/BigFast/Downloads/naclient.pkg”;
PKInstallPackageIdentifier = “com.vmware.sslvpn”;
Installer[4097]: install:didFailWithError:Error Domain=PKInstallErrorDomain Code=112 “An error occurred while running scripts from the package “naclient.pkg”.” UserInfo=0x7f9c8536ce10 {NSFilePath=./preinstall, NSURL=file://localhost/Volumes/BigFast/Downloads/naclient.pkg, PKInstallPackageIdentifier=com.vmware.sslvpn, NSLocalizedDescription=An error occurred while running scripts from the package “naclient.pkg”.}
Installer[4097]: Install failed: The Installer encountered an error that caused the installation to fail. Contact the software manufacturer for assistance.
Installer[4097]: IFDInstallController 83028370 state = 7
Installer[4097]: Displaying ‘Install Failed’ UI.
Installer[4097]: ‘Install Failed’ UI displayed message:’The Installer encountered an error that caused the installation to fail. Contact the software manufacturer for assistance.’.
installd[4110]: installd: Exiting.

This error is really not useful, but by looking within the installer package itself I could see that it is using /tmp/naclient_install.log for the install scripts themselves.  Within this log there is a bit more clue as to why it failed:

/tmp/naclient.pkg/Contents/Resources/preinstall: kernel version mismatch
/Volumes/BigFast/Downloads/naclient.pkg/Contents/Resources/preinstall: kernel version mismatch
/Volumes/BigFast/Downloads/naclient.pkg/Contents/Resources/preinstall: kernel version mismatch

In order to fix this you need to define the Mountain Lion kernel as being valid.  To do this, instead of installing the SSL VPN client from the web interface select to download the zipped file.

Extract the contents of the file and you will have a “naclient.pkg” file.  Like many “files” on OSX, this is actually just a special directory…you can either access the contents via CLI or right-click (or Ctrl-Click) and select to “Show Package Contents”.

If we look at the installation scripts themselves (with the arrows above) we find that the scripts are running a uname command to determine OS version:  uname -r | cut -d. -f1

We can also see that they were nice enough to support all the way back to Panther (released in 2003) but that there is no definition for Mountain Lion.

If we execute this command on Mountain Lion the response is “12”, however “12” is not defined as a valid kernel version.  The reality is that Mountain Lion is close enough for most apps to be considered “Lion”, so we will add this definition just the same as for Lion itself.

We will edit the 4 files that are indicated with the arrows, these are shell scripts and you can edit them with your text editor of choice, all 4 files need to be edited exactly the same just adding a definition for Mountain Lion.

Save your changes to all four files including “postinstall”, “postupgrade”, “preinstall”, and “preupgrade”.

Browse up the directory structure until you see the naclient.pkg and run the installer again.

***** Yosemite Update ******

Any of you that have upgraded to Yosemite may find that you cannot connect to the VPN afterword, it fails to establish a connection with an error somewhat like this:


In order to fix this here are the steps I took (PROCEED AT YOUR OWN RISK):

  1. Unistall NAclient:  sudo /opt/sslvpn-plus/naclient/uninstall.sh
  2. Enabled developer mode for Kext insertion:  sudo nvram boot-args=”kext-dev-mode=1″
  3. Rebooted
  4. Installed the NAclient again

I owe thanks to @jakerobinson for this as he actually found the solution.

***** Yosemite Update 01-07-2014 ******

Unfortunately it is not possible to get the naclient to run in any reliable fashion on Yosemite.  I have spent a lot of time on this and ended up using a Mavericks VM in Fusion to get the client to work for the day job.

naclient is dependent up on some kexts to load at system boot, however the method invoked to start these has been deprecated for multiple major releases of OS X and were removed in Yosemite.  The problem extends beyond the lack of signing, it is another example of VMware failing to support OS X even as the company issues Apple systems to a large number of employees and all new systems come with Yosemite pre-installed.

I will try to find time to write up my work around, it uses a VM but allows me to use that VM as a very heavy VPN client but I am able to use my (limited) apps in Yosemite as I normally would.

***** El Capitan 10.11.1+ Update 11-19-2015 ******

Rather than keep adding content to this post, I created  new blog post with the work around for OS X El Capitan and it can be found here.