I have seen in a post here that when you want to deployed an exe file octopus is capable to deploying it because it is in a way packed. But the automatic installation of the package setup on the target machine might be a bit tricky.
for instance if a setup need to be installed without user intervention, we should be be able to run the installer in silent mode to avoid user interaction.
Q 1But how to handle unnattended setting parameters which can be pass to the installer like installation path, database connection,…?
Q2 : In case a previous version is already running at the target and we are trying to install the new package, how it is behaving ?
Or more in generla is i better to do such package installation manually and let final user run it ?
This is an interesting question, and really comes down to the software that you are installing. The first thing you will need to do is package your .EXE file in such a way that Octopus can understand it, a good place to start would be a .ZIP file following semver naming conventions which you can then upload to the internal package feed of your Octopus server.
What I would then do is use combination of Octopus variables and a powershell script step which has a package attached to deploy the package and add the required settings parameters.
For your second question, that is very much down to how your application runs. Again I would use the powershell script that we created above, but add checks to see if the application is running then close that process before upgrading to the new version. The most simple way of accomplishing this is by terminating the process of your application, however depending on how it’s designed this may cause undesirable behaviour. This thread will help you get started with a process to cleanly close the application, however this is trickier to accomplish.
I would try and avoid any user intervention if at all possible.
Hopefully that helps, please let me know if you have any further questions,