The JDWP specification guarantees that the ordering of events and replies will accurately reflect the order of suspends/resumes done by the corresponding commands and events. The current JDWP implementation does not conform in that it takes no special actions to guarantee the order. There is no easy test case to demonstrate this as the guarantee will be broken only with certain timings.
Here is the latest JDWP spec (Mustang/JDK1.6.0):

http://java.sun.com/javase/6/docs/platform/jpda/jdwp/jdwp-protocol.html

> EventRequest Command Set (15)
>
> Set Command (1)

<snip>

> Out Data

<snip>

> byte suspendPolicy What threads are suspended when this event occurs?
> Note that the order of events and command replies
> accurately reflects the order in which threads are
> suspended and resumed. For example, if a VM-wide
> resume is processed before an event occurs which
> suspends the VM, the reply to the resume command
> will be written to the transport before the
> suspending event.