diff --git a/windows/Toolbox.iss b/windows/Toolbox.iss
index 70fd12a7..15162137 100644
--- a/windows/Toolbox.iss
+++ b/windows/Toolbox.iss
@@ -323,6 +323,7 @@ begin
   begin
     WizardForm.StatusLabel.Caption := 'Migrating Boot2Docker VM...'
     WizardForm.FilenameLabel.Caption := 'This will take a minute...'
+    ExecAsOriginalUser(ExpandConstant('{app}\docker-machine.exe'), ExpandConstant('rm -f default > nul 2>&1'), '', SW_HIDE, ewWaitUntilTerminated, ResultCode)
     DelTree(ExpandConstant('{userdocs}\..\.docker\machine\machines\default'), True, True, True);
     ExecAsOriginalUser(ExpandConstant('{app}\migrate.bat'), ExpandConstant('> {localappdata}\Temp\toolbox-migration-logs.txt 2>&1'), '', SW_HIDE, ewWaitUntilTerminated, ResultCode)
     if ResultCode = 0 then
diff --git a/windows/start.sh b/windows/start.sh
index 582af3a6..a9cb0490 100644
--- a/windows/start.sh
+++ b/windows/start.sh
@@ -16,6 +16,7 @@ set -e
 
 if [ $VM_EXISTS_CODE -ne 0 ]; then
   echo "Creating Machine $VM..."
+  $DOCKER_MACHINE rm -f $VM &> /dev/null || :
   rm -rf ~/.docker/machine/machines/$VM
   $DOCKER_MACHINE create -d virtualbox --virtualbox-memory 2048 $VM
 else