VMWare Fusion won't install VMWare Tools on Mac OS X Server 10.6

[pb_vmw]

The summary of my problem is in the title.

I am running a Mac OS X Server 10.6 virtual machine using the latest version of VMWare Fusion (11.5.1) under macOS Mojave 10.14.6 (18G95). Each time that I try to install VMWare Tools in this machine the installation fails. The details of the error message are seen in the attached screenshot.

Is there anything I can do about it? I tried the suggestion to repeat the installation but this makes no difference whatsoever.

Thanks!

[dempson]

As a data point, I updated VMware Tools in my existing 10.6 Server VM using VMware Fusion 11.5.1 on Mojave 10.14.6 (18G2022), and it ran through without error. I was also able to uninstall then reinstall VMware Tools. As it happens, that VM's tools were slightly out of date: they got updated from "10.0.12.334 (build-4448496)" to "10.0.12.2027 (build-11054227)".

In case it matters: is your guest 10.6 Server fully up to date? Mine is running 10.6.8 with the final security update (shows as build 10K549, but that does not indicate whether the security update was installed because Snow Leopard's security updates didn't change the build number).

You can probably get more information about why the error is occurring by looking at the installer log. While the error indication is shown, click on View > Installer Log, which opens another window. It has a pop-up menu to select the level of detail (default is "Show Errors Only"; I normally pick "Show All Logs" to see as much context as possible).

[pb_vmw]

This is interesting. I managed to take a screenshot of the error details which I attach here (obviously copy-paste do not work). It says essentially that the VMWare Tools package cannot be trusted (there is something like an expired certificate, if I interpret correctly what I see). I tried the VMWare Tools installation in a fresh Snow Leopard Server installation and I get the same error.

[pb_vmw]

> In case it matters: is your guest 10.6 Server fully up to date? Mine is running 10.6.8 with the final security update (shows as build 10K549, but that does not indicate whether the security update was

> installed because Snow Leopard's security updates didn't change the build number).

Yes, it is the same build as in yours. But now its internet access suddenly is interrupted. I compared the network settings with the freshly created Snow Leopard Server VM and I saw that they are the same. Besides I changed nothing. I don't understand why the old VM stopped all internet connections by its own while the new one, with the same settings, works (as it should of course).

[dariusd · Accepted solution]

The Mac OS X installer is somewhat unusual in that it seems to expect that digitally-signed code is only valid until the expiry of the code-signing certificate used for the digital signature.

You might need to work around the problem by setting your virtual machine's clock back a few months/years and then install the package.  If you already have Mac OS X Server installed, you should be able to use the Date & Time pane in System Preferences to disable automatic time sync and manually set the clock back far enough for the installation to proceed.  Remember to set the clock back to the current date and time and/or re-enable time sync if desired.

Thanks,

--

Darius

[dempson]

Looking back through my VM's /var/log/install.log I see these lines corresponding to your screen shot:

Dec 28 10:43:45 Snow-Leopard-VM Installer[1700]: IFPKInstallElement (1 packages)

Dec 28 10:43:45 Snow-Leopard-VM Installer[1700]: PackageKit: allowing untrusted file://localhost/Volumes/VMware%20Tools/Install%20VMware%20Tools.app/Contents/Resources/VMware%20Tools.pkg#files.pkg under guise of unsigned

Dec 28 10:43:45 Snow-Leopard-VM installd[1825]: PackageKit: ----- Begin install -----

Looking more closely at that "VMware Tools.pkg" file with Suspicious Package, it has an expired certificate (10 October 2018). For some reason, my Snow Leopard VM's Installer is ignoring the fact that certificate has expired and treating it as unsigned, but yours is apparently refusing to proceed.

One of the updates for Snow Leopard was "Apple Software Installer Update 1.0". The description claims it only affects installation of Apple software updates, but it does include an updated version of /System/Library/PrivateFrameworks/PackageKit.framework. Did that update get installed on your Snow Leopard system after 10.6.8?

If I do a Get Info on my PackageKit.framework, it is version 1.1.4, which matches the version in the Apple Software Installer Update manual download.

As dariusd suggests, you can probably work around the issue by disconnecting your VM's clock from the host and setting it manually far enough back (possibly before 10 October 2018).

[pb_vmw]

Thank you so much! Indeed, setting date and time a few years back solved the problem.