The backing container implementations can not handle a automatic redeploy of a same named archive and will in some cases silently ignore the call. This is a programming error that cause confusion.

If redeploy support is requested as a feature, a proper API/SPI should be put in place.

@Deployment(name = "X")
   return ShrinkWrap.create(JavaArchive.class, "test.jar")

@Deployment(name = "Y")
   return ShrinkWrap.create(JavaArchive.class, "test.jar")

This will cause "java.lang.IllegalArgumentException: Can not add multiple org.jboss.shrinkwrap.api.Archive archive deployments with the same archive name test.jar that target the same target DEFAULT"

@Deployment(name = "X") @TargetsContainer("X")
   return ShrinkWrap.create(JavaArchive.class, "test.jar")

@Deployment(name = "Y") @TargetsContainer("Y")
   return ShrinkWrap.create(JavaArchive.class, "test.jar")