diff --git a/lib/helpers/gem_exec.rb b/lib/helpers/gem_exec.rb
index fdff62859..5fdc77a61 100644
--- a/lib/helpers/gem_exec.rb
+++ b/lib/helpers/gem_exec.rb
@@ -37,12 +37,20 @@ class GemExec
     end
 
     Dir.chdir(working_dir)
-    output_hash = {:output => '', :status => 0}
+    output_hash = {:output => '', :status => 0, :exception => nil}
     begin
-      output_hash[:output] = ProcessHelper.process("#{gem_path} #{arguments}", {:timeout => (60*40)})
+      output_hash[:output] = ProcessHelper.process("#{gem_path} #{arguments}", {:timeout => (30),
+                                                                                include_output_in_exception: true})
     rescue Exception => ex
-      output_hash[:output] = ex.to_s.split('Command output: ')[1]
       output_hash[:status] = 1
+      output_hash[:exception] = ex
+      if ex.type == ProcessHelper::UnexpectedExitStatusError
+        output_hash[:output] = ex.to_s.split('Command output: ')[1]
+      elsif ex.type == ProcessHelper::TimeoutError
+        output_hash[:output] = ex.to_s.split('Command output prior to timeout: ')[1]
+      else
+        output_hash[:output] = nil
+      end
     end
     output_hash
   end
diff --git a/secgen.rb b/secgen.rb
index 02914542a..f39470c86 100644
--- a/secgen.rb
+++ b/secgen.rb
@@ -149,7 +149,7 @@ def build_vms(project_dir, options)
     else
       if retry_count > 0
         # Identify which VMs failed
-        if vagrant_output[:output] != nil
+        if vagrant_output[:exception].type == ProcessHelper::UnexpectedExitStatusError
           split = vagrant_output[:output].split('==>')
           failures = []
           split.each do |line|
@@ -177,7 +177,8 @@ def build_vms(project_dir, options)
           GemExec.exe('vagrant', project_dir, 'destroy')
         end
       else
-        Print.err 'Error creating VMs, exiting SecGen.'
+        Print.err 'Error provisioning VMs, destroying VMs and exiting SecGen.'
+        GemExec.exe('vagrant', project_dir, 'destroy')
         exit 1
       end
     end