Fix - Issues when Installing SSMS on an Offline Virtual Machine

I recently had to install SQL Server Management Studio (SSMS) offline on a virtual machine. The machine was running Windows Server 2022.

I struggled for many hours, and came to the conclusion that this should not be as difficult as it was. I hope this information helps someone else.

I followed the instructions provided for offline installation from here: Create an Offline Installation of SQL Server Management Studio . Erin Stellato did a good job in that article and that almost could have worked but there were a few issues.

VS Installer Silently Closing

I started by using the command:

vs_setup.exe --layout

That downloads the required files for an offline install. Importantly, if you then move these files to the offline location, it won’t just install. Erin had a note on that page about the installer silently closing if you didn’t have the certificates installed. I missed that part when I first read it. I’ve suggested that the page needs a troubleshooting section with the issue as a header, as it doesn’t currently win the SEO battle.

But even after I did install them from the certificates folder, it still was closing silently. I ended up writing a program that followed the certificate chains that were required, and it wasn’t just those three that were needed. I found that these three certificates were also needed:

SSMS Install Missing Certificates

I’m not sure what the official source of those is, but I found them somewhere and installed them. And once I installed those, the setup would continue to run.

ISO and long file names

Next issue I ran into was the use of very long file names. I needed to create an ISO image with the installation files, so I could attach it to the VM for installation.

I started by creating a program that would copy the downloaded files into an ISO image.

After creating it, and attaching it, the install was failing in all sorts of weird ways. But when I checked the logs, there were files apparently missing. But I checked they were there in my source.

That took me a while to work out.

The issue is that the ISO standard doesn’t support file names longer than 256 characters. And the installer for VS/SSMS has files with names longer than 256 characters.

So I needed to change that plan. Zip files can hold longer names, so what I did was to zip the folder and put the zip into the ISO image rather than the files.

And then it was working.