How to monitor and log manual installation

I need to investigate the installation of a product that consists out of several setup.exe files, MSI installers and related prerequisites. My thoughts are; I perform the installation manually and another piece of software monitors and logs what is installed and when it is installed. So I can figure out the sequence the software is installed so I can package it.

Deployment / Installation: The better way to do this would be to install the MSI files in the correct sequence once you have extracted them all from the setup.exe files. You can then install all required components via a distribution system, or even just via a batch file.

Even without extraction you can install the different components via a batch file or a distribution system such as SCCM - if you figure out what switches to use for the setup.exe to run them reliably in silent mode (which is not always that easy - and sometimes impossible, and generally always somewhat unreliable - which is why we tend to convert legacy setup.exe files to MSI format - or App-V). Check this answer for a description of how to run various setup.exe files in silent mode (towards bottom). They are not created the same, and they support very different switches depending on what tools they were made with (WiX Burn, Installshield, Wise, Advanced Installer, PACE Suite, Wise, Inno Setup, NSIS, etc... See more on these tools below). MSI tools (includes the free, open source WiX toolkit). Non-MSI tools.

To get a rough idea of what has been installed by running your deployment operation, you could check the list of installed product in Add / Remove Programs before and after installation. Products can be installed without showing up here - which I am sure you are aware of. Working out the exact details can take quite a while. You can also check event logs and see what new shortcuts were created on the start menu, if any. You can also compare the disks (installation folders) of a clean and a deployed virtual machine. There are many tricks and ways to get an idea of what was installed. The best is often to run in interactive mode and see what each installation screen tells you about what is being installed. Also look for documentation embedded in the setups or in installation folders after installation.

Overall - if you ask me - I would say: Get on the phone and call the software vendor and ask for their documentation on the deployment of their software. They should be able to provide both documentation, examples and basic help on what is necessary to run their software solution. And the good, real-world advice that they just didn't get time to add to their documentation - or was acquired after it was written. The real solutions. If they can't, why not question the whole software solution? I have wanted to throw out dysfunctional software many times, based on their poor deployment strategies. A massive cost for clients to deal with, and sometimes impossible to fix in reliable ways.

Extract Setup.exe: I have an "organically evolved" answer here on the issue of setup.exe extraction - in other words getting the MSI files (if any) out of the wrapper setup.exe files. When I say organic, I mean that the answer has been updated so many times that it has become a structured mess, but it is still OK information if you take the time to read it (I think): Extract MSI from EXE.

Capture / Repackaging: It is possible to "capture" the installation of legacy setup.exe files and convert them to MSI format, or App-V which many corporations use as their deployment format these days. They usually use repackaging tools (list from installsite.org) to do this, and they are available as commercial tools like AdminStudio (from Installshield now Flexera), Advanced Installer Architect, PACE Suite, etc... There used to be several free capture tools out there, but they tend to disappear over time as they don't get maintained. MSI files should generally not be repackaged - it is very ill-advised to try to do so - they are almost always possible to run reliably in silent mode, barring a few relatively common design flaws (that can usually be resolved with acceptable efforts by trained packagers). If your organization uses App-V, though, then this is often what they do - repackage MSI installations - and other types of installations.