VMware & Windows 7 | "Install VMware Tools" Greyed Out

1. Where to download Windows 7?

As of Nov. 2024, this archive.org link is available. Considering the purpose of my installation is for testing, so I accept the potential risk of it. It's not Microsoft official link, use with your own risk. Microsoft official link is not available

2. Key steps

1. Use Easy Install method
2. No activation key (My testing period is short, no key needed.)
3. Default settings
4. After installation, turn off "Side Channel Mitigations" if you need.

3. Install VMware Tools

Key points:

1. Should install KB4490628, KB4474419 manually.
   As VMware article 78708 pointed out, Microsoft has changed Windows driver signing to use SHA-2 algorithm exclusively starting December 3, 2019, legacy Windows systems without SHA-2 code signing support will fail driver signature verification.
   

2. Should remove CD/DVD drive and add a new one.
   After Windows 7 guest installation, the .iso of Windows 7 installation image file occupies the guest's CD/DVD drive. So should delete it and add a new one.

Steps:

1. Install KB4490628, KB4474419 in Windows 7:

   Without VMware tools, you can not copy and paste anything from host to guest. These updates should download in guest. But IE is too old to visit most sites. Two options:

   1. IE browser: Tools -> Internet Options -> Advanced -> Security. Enable all SSL and TLS options:
      
      This will prevent "cannot display" error:

      

      But, after SSL and TLS options enabled, each time you visit an HTTPS site, it still will sometimes prompt you:

      

      Just continue to it, if you know it is a good site.

   2. Use IE search Firefox and install:

      

      It looks like only ESR version of Firefox is capable to Windows 7.

   3. Search KB4490628 and KB4474419 separately, find the "Microsoft Update Catalog" Link:

      

   4. Restart Windows 7 guest

2. Remove and add new CD/DVD drive for Windows 7 guest

According to this article on ghacks.net, after Windows 7 installation finished, should shut down Windows 7 guest, remove its CD/DVD drive (mounted Windows 7 .iso file) then add a new one:

1. Shut down the virtual machine.
2. Open VMWare Workstation Player and right-click on the VM. (Don't start the VM)
3. Select the "Settings" option to edit the hardware settings.
4. Highlight the CD/Drive on the left sidebar under the Hardware tab and click on the remove button.
5. Repeat the above step to remove the Floppy Drive. (This step seems unnecessary, but it works for me.)
6. Click on the "Add button" and select "CD/DVD" Drive and select finish. The right pane should now have the option "Use Physical Drive > Auto Detect" enabled. (Previously, it had the Windows ISO selected)
7. Click on "OK" to close the window, and Start the VM as usual.
8. Once it has booted to the desktop, click on the menu at the top left corner and go to "Player > Manage > Install VMWare Tools".

Tools for Windows 7

1. Mounting disk image files tool: Wincdemu (Open source)