I have previously suggested a worst case behaving JVM for test purposes on the memory model list but the idea didn't seem popular.
So how to gain "worst case JVM behaviour" , with existing technology i.e how can I test the scenario in the question and get it to fail EVERY time. You could try to find the setup with the weakest memory model possible but that's unlikely to be perfect.
What I have often considered is using a distributed JVM something similar to how I believe Terracotta works under the cover so your application now runs on multiple JVM's (either remote or local) (threads in the same application run in different instances). In this setup inter JVM thread communication takes place at memory barriers e.g. the synchronized keywords you are missing in bugged code for instance (it conforms to the Java Memory Model) and the application is configured i.e. you say this class thread runs here . No code change required to your tests just configuration, any well ordered java application should run out of the box, however this setup would be very intolerant of a badly ordered application (normally a problem ... now an asset i.e. the Memory model exhibits very weak but legal behavior). In the example above loading the code onto a cluster, if two threads run on different nodes setValue has no effect visible to the other thread unless the code was changed and synchronized, volatile etc etc were used, then the code works as intended.
Now your test for the example above (configured correctly) would fail every time without correct "happens before ordering" which is potentially very useful for tests. The flaw in the plan for complete coverage you would need a potentially a node per application thread (can be same machine or multiple in a cluster) or multiple test runs. If you have 1000's of threads then that could be prohibitive though hopefully they would be pooled and scaled down for E2E test scenarios or run it in a cloud. If nothing else this kind of setup might be useful in demonstrating the issue.
inter thread communication across JVMs