Do Specialized Images have the same machine SIDs? Yes.

Please see Mark Russinovich’s blog post: The Machine SID Duplication Myth (and Why Sysprep Matters)

The more I thought about it, the more I became convinced that machine SID duplication – having multiple computers with the same machine SID – doesn’t pose any problem, security or otherwise. I took my conclusion to the Windows security and deployment teams and no one could come up with a scenario where two systems with the same machine SID, whether in a Workgroup or a Domain, would cause an issue. At that point the decision to retire NewSID became obvious.

I realize that the news that it’s okay to have duplicate machine SIDs comes as a surprise to many, especially since changing SIDs on imaged systems has been a fundamental principle of image deployment since Windows NT’s inception. This blog post debunks the myth with facts by first describing the machine SID, explaining how Windows uses SIDs, and then showing that - with one exception - Windows never exposes a machine SID outside its computer, proving that it’s okay to have systems with the same machine SID.

Kerberos and NTLM authentication failures due to duplicate SIDs - Microsoft Support

Potential impact to Instant Clones from Microsoft Windows update KB5065426 (6001154)

Windows 11-24H2 Update KB5065426 Causes RDP, File Sharing And Printer Connectivity Issues With PVS And MCS Machines