I have a fairly complicated Jenkins job that builds, unit tests and packages a web application. Depending on the situation, I would like to do different things once this job
If I understood it correct you should be able to do this by following these Steps:
Do the same for the high-risk job
Now you should have the following Setup:
And that's what you wanted to achieve. Isn't it?
Do you use Ant for your builds?
If so, it's possible to do conditional building in ant by having a set of environment variables your build scripts can use to conditionally build. In Jenkins, your build will then be building all of the projects, but your actual build will decide whether it builds or just short-circuits.
Have you looked at the Conditional Build Plugin? (https://wiki.jenkins.io/display/JENKINS/Conditional+BuildStep+Plugin)
I think it can do what you're looking for.
If you want a conditional post-build step, there is a plugin for that:
https://wiki.jenkins-ci.org/display/JENKINS/Post+build+task
It will search the console log for a RegEx you specify, and if found, will execute a custom script. You can configure fairly complex criteria, and you can configure multiple sets of criteria each executing different post build tasks.
It doesn't provide you with the usual "build step" actions, so you've got to write your own script there. You can trigger execution of the same job with different parameters, or another job with some parameters, in standard ways that jenkins supports (for example using curl)
Yet another alternative is Jenkins text finder plugin:
https://wiki.jenkins-ci.org/display/JENKINS/Text-finder+Plugin
This is a post-build step that allows to forcefully mark a build as "unstable" if a RegEx is found in console text (or even some file in workspace). So, in your build steps, depending on your conditions, echo a unique line into console log, and then do a RegEx for that line. You can then use "Trigger parameterized buids" and set the condition as "unstable". This has an added benefit of visually marking the build different (with a yellow ball), however you only have 1 conditional option with this method, and from your OP, looks like you need 2.
Try a combination of these 2 methods:
The simplest approach I found is to trigger other jobs remotely, so that you can use Conditional Build Plugin or any other plugins to build other jobs conditionally.
I think the way to do it is to add an intermediate job that you put in the post-build step and pass to it all the parameters your downstream jobs could possibly need, and then within that job place conditional builds for the real downstream jobs.