diff --git a/spec/support/shared/contexts/metasploit/framework/spec/constants/cleaner.rb b/spec/support/shared/contexts/metasploit/framework/spec/constants/cleaner.rb
index 345552c8d6190..767c604625540 100644
--- a/spec/support/shared/contexts/metasploit/framework/spec/constants/cleaner.rb
+++ b/spec/support/shared/contexts/metasploit/framework/spec/constants/cleaner.rb
@@ -1,6 +1,8 @@
 # Use in a context to clean up the constants that are created by the module loader.
 RSpec.shared_context 'Metasploit::Framework::Spec::Constants cleaner' do
   after(:example) do
+    $stderr.puts "cleaning constants"
     Metasploit::Framework::Spec::Constants.clean
+    $stderr.puts "constants cleaned"
   end
-end
\ No newline at end of file
+end
diff --git a/spec/support/shared/contexts/msf/framework/threads/cleaner.rb b/spec/support/shared/contexts/msf/framework/threads/cleaner.rb
index 758fd0988bd48..b2c6c62acf2a1 100644
--- a/spec/support/shared/contexts/msf/framework/threads/cleaner.rb
+++ b/spec/support/shared/contexts/msf/framework/threads/cleaner.rb
@@ -1,5 +1,6 @@
 RSpec.shared_context 'Msf::Framework#threads cleaner' do |options = {}|
   after(:example) do |example|
+    $stderr.puts "starting to kill threads"
     if options.fetch(:verify_cleanup_required, true) && !framework.threads?
       fail RuntimeError.new(
                "framework.threads was never initialized. There are no threads to clean up. " \
@@ -11,14 +12,24 @@
     # explicitly kill threads so that they don't exhaust connection pool
     thread_manager = framework.threads
 
+    $stderr.puts "starting to kill threads"
     thread_manager.each do |thread|
+      puts "-----------------------------------------------------"
+      thread_deets = "thread=#{thread} - name=#{thread[:tm_name]} --- backtrace=#{thread.backtrace ? thread.backtrace.join("\n") : 'no backtrace'} ---"
+      $stderr.puts "killing thread #{thread_deets}"
       thread.kill
+      $stderr.puts "Waiting to join"
       # ensure killed thread is cleaned up by VM
       thread.join
+      $stderr.puts "Joined on thread"
+      $stderr.puts
     end
 
+    $stderr.puts "Killing thread manager monitor"
     thread_manager.monitor.kill
     # ensure killed thread is cleaned up by VM
+    $stderr.puts "Joining killed thread monitor"
     thread_manager.monitor.join
+    $stderr.puts "successfully joined thread monitor"
   end
 end
diff --git a/spec/support/shared/contexts/msf/simple/framework.rb b/spec/support/shared/contexts/msf/simple/framework.rb
index 8d7bc31e8868f..6a0982fce09bf 100644
--- a/spec/support/shared/contexts/msf/simple/framework.rb
+++ b/spec/support/shared/contexts/msf/simple/framework.rb
@@ -23,6 +23,8 @@
   end
 
   after(:example) do
+    $stderr.puts "before cleaning framework path"
     FileUtils.rm_rf(dummy_pathname)
+    $stderr.puts "after cleaning framework path"
   end
 end