I can't install VMware Tools on my MacOS 10.9.5 VM

[jbaughccm]

I've created a VM using MacOS 10.9.5.  I am unable to do any sharing, dragging and dropping actions because VMware Tools is not installed.  When I try to install the Tools, I get as far as the "Destination Select" step where I am asked to Select a Destination.  Only three options are available (Install for all users of this computer, Install for me only, and Install on a specific disk...) all of which are grayed out and not selectable.  The message at the bottom of the screen says, "You cannot install VMware Tools in this location. The VMware Tools installer does not allow its software to be installed here."

I'm guessing that VMware Tools is not compatible with MacOS 10.9.5?  Or am I missing something?  I sure would like the ability to drag and drop files between my Mac OS Sonoma desktop and my Mac OS 10.9.5 VM.

John

[scott28tt]

What type of CPU does your Mac have, and what version of Fusion are you using?

[jbaughccm]

My Mac is a 2020 iMac with3.6GHz 10-Core Intel corei9 processor with 64GBRAM running Sonoma 14.0.

Fusion version is 13.0.2

John

[ColoradoMarmot]

Officially Fusion has dropped support for that version of MacOS, but you should still be able to get the tools installed.

Couple of things - First, is this a real installer from Apple?  If not, that's step 1 to fix.  Second, did you use the easy install wizard to create the VM initially?  If not, that's the best option as it'll configure the OS type properly, so you may want to start over.  In either case, make sure the OS type is set properly in the VM Settings (I suspect that's the most likely cause, and it's trying to install the wrong tools).  Also, when you setup the guest make sure it is not a case-sensitive file system.

Next, make sure you're using an administrator account in the guest.  No other type will work properly.

Last, try setting the guest system clock back to 2018 and then running the installer.  The signatures on the code have expired, but I'm not sure if Mavericks is getting hit with that or not.

[jbaughccm]

I installed the VMware version of MacOS 10.9.5 by migrating it from my Parallels .pvm version.  I have an old copy of the "Install OS X Mavericks" installer.  But I never could get it to install.  Every attempt resulted in an error message early in the installation process.  I believe it said that the installer might be corrupted or something to that effect.  I found instructions on the web that said to first set the system clock back to 2018 and then try.  I couldn't get this to work either. I do know that when I installed my VMWare version the installation process did not give me the opportunity to identify the OS version as MacOs 10.9.  I believe it would only let me select OS 10.7. As you point out, this may be the major problem here.

I appreciate your suggestions. But I am a bit of a novice using VMware Fusion.  I have used Parallels for many years, but I'm trying to migrate away from that money hole.

John

[jbaughccm]

The only reason I need to use MacOS 10.9x is that it is the latest version of MacOS that will run my version of FileMaker Pro. I have a large database of FMP files and I can't see the expense and effort to upgrade to a newer version. 

John

[jbaughccm]

I just tried to do an install again using my Mavericks installer.  Same failure error.  See screenshot.

John

[jbaughccm]

You are correct about the OS type being set incorrectly in VMware. As you can see from the image, the file is recognized as "Mac OS X Server 10.6". Apparently that is the OS under which it was created in Parallels?

John

[Technogeezer]

It’s possible that the conversion process set the macOS version to the wrong value. 

[ColoradoMarmot]

Try changing that to 10.9, and then install the tools.

Couple of other thoughts:  I'm not sure if Parallels import is supported for MacOS, but might be worth checking.  And definitely remove the parallels tools from parallels before trying to import.  Building from scratch is always a better option.

Just a head's up though, when you move to apple silicon, you will have to upgrade your filemaker.  There's no MacOS virtualization on M1's, let alone for Intel OS's.

[jbaughccm]

"Just a head's up though, when you move to apple silicon, you will have to upgrade your filemaker.  There's no MacOS virtualization on M1's, let alone for Intel OS's."

I hadn't considered that.  All 4 of my other Macs are Apple Silicon. My iMac is my only hold out.  It will likely be retired or replaced in the near future. So even if I get this working smoothly it will only be a temporary fix.  Maybe I need to consider taking the leap and trying to migrate my legacy FileMaker Pro to the new and improved ( and very expensive) new version.

Thanks.

John

[ColoradoMarmot]

Yeah, it's a 'breaking change' for MacOS software, like when they dropped 32-bit support (most of my game library stopped working).

If it was a windows application, it might run under Windows 11 ARM (it has a rosetta-like option), but I don't know if that's an option in your case.