Github user aledsage commented on a diff in the pull request:

    https://github.com/apache/brooklyn-server/pull/110#discussion_r59183890
  
    --- Diff: 
locations/jclouds/src/main/java/org/apache/brooklyn/location/jclouds/JcloudsLocation.java
 ---
    @@ -2742,14 +2743,53 @@ protected LoginCredentials 
waitForWinRmAvailable(final ComputeService computeSer
                 Callable<Boolean> checker = new Callable<Boolean>() {
                     public Boolean call() {
                         for (Map.Entry<WinRmMachineLocation, LoginCredentials> 
entry : machinesToTry.entrySet()) {
    -                        WinRmMachineLocation machine = entry.getKey();
    -                        WinRmToolResponse response = 
machine.executeCommand(
    -                                
ImmutableMap.of(WinRmTool.PROP_EXEC_TRIES.getName(), 1),
    -                                ImmutableList.of("echo testing"));
    -                        boolean success = (response.getStatusCode() == 0);
    -                        if (success) {
    -                            credsSuccessful.set(entry.getValue());
    -                            return true;
    +                        try {
    +                            final WinRmMachineLocation machine = 
entry.getKey();
    +                            WinRmToolResponse response = 
machine.executeCommand(
    +                                    
ImmutableMap.of(WinRmTool.PROP_EXEC_TRIES.getName(), 1),
    +                                    ImmutableList.of("echo testing"));
    +                            boolean success = (response.getStatusCode() == 
0);
    +                            if (success) {
    +                                credsSuccessful.set(entry.getValue());
    +//                                final String pendingRebootStatusScript = 
"C:\\Get-PendingReboot.ps1";
    --- End diff --
    
    Is the reboot because you are testing on vCloud Director, and it is the 
vmware tools that is doing the reboot? My understanding in that situation is 
that the vApp template can include configuration that causes a reboot of the 
VM. Given that situation is not about upgrades, then the Windows OS does not 
know it is going to be rebooted until the vmware tools issues the reboot 
command.
    
    It also wouldn't surprise me if there is a race: when the VM first boots, 
it checks to see if there are any security updates that need applied and 
whether those updates require reboot; but while it is still checking we are 
able to connect to the VM over WinRM so we might check too early.


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