diff --git a/lib/bolt/transport/docker/connection.rb b/lib/bolt/transport/docker/connection.rb
index 47440503e6..6921685a1a 100644
--- a/lib/bolt/transport/docker/connection.rb
+++ b/lib/bolt/transport/docker/connection.rb
@@ -79,6 +79,7 @@ def execute(*command, options)
         end
 
         def write_remote_file(source, destination)
+          @logger.debug { "Uploading #{source}, to #{destination}" }
           _, stdout_str, status = execute_local_docker_command('cp', [source, "#{container_id}:#{destination}"])
           raise "Error writing file to container #{@container_id}: #{stdout_str}" unless status.exitstatus.zero?
         rescue StandardError => e
@@ -86,6 +87,7 @@ def write_remote_file(source, destination)
         end
 
         def write_remote_directory(source, destination)
+          @logger.debug { "Uploading #{source}, to #{destination}" }
           _, stdout_str, status = execute_local_docker_command('cp', [source, "#{container_id}:#{destination}"])
           raise "Error writing directory to container #{@container_id}: #{stdout_str}" unless status.exitstatus.zero?
         rescue StandardError => e
diff --git a/lib/bolt/transport/local/shell.rb b/lib/bolt/transport/local/shell.rb
index c2d6d7c45c..1a2807e68f 100644
--- a/lib/bolt/transport/local/shell.rb
+++ b/lib/bolt/transport/local/shell.rb
@@ -73,6 +73,7 @@ def handle_sudo_errors(err, pid)
         end
 
         def copy_file(source, dest)
+          @logger.debug { "Uploading #{source}, to #{dest}" }
           if source.is_a?(StringIO)
             File.open("tempfile", "w") { |f| f.write(source.read) }
             execute(['mv', 'tempfile', dest])
diff --git a/lib/bolt/transport/local_windows.rb b/lib/bolt/transport/local_windows.rb
index 0012290712..91030855cd 100644
--- a/lib/bolt/transport/local_windows.rb
+++ b/lib/bolt/transport/local_windows.rb
@@ -47,6 +47,7 @@ def in_tmpdir(base)
       private :in_tmpdir
 
       def copy_file(source, destination)
+        logger.debug { "Uploading #{source}, to #{destination}" }
         FileUtils.cp_r(source, destination, remove_destination: true)
       rescue StandardError => e
         raise Bolt::Node::FileError.new(e.message, 'WRITE_ERROR')
diff --git a/lib/bolt/transport/ssh/connection.rb b/lib/bolt/transport/ssh/connection.rb
index 1cba98b251..8599713032 100644
--- a/lib/bolt/transport/ssh/connection.rb
+++ b/lib/bolt/transport/ssh/connection.rb
@@ -261,6 +261,8 @@ def execute(command, sudoable: false, **options)
         end
 
         def copy_file(source, destination)
+          # Do not log wrapper script content
+          @logger.debug { "Uploading #{source}, to #{destination}" } unless source.is_a(StringIO)
           @session.scp.upload!(source, destination, recursive: true)
         rescue StandardError => e
           raise Bolt::Node::FileError.new(e.message, 'WRITE_ERROR')
diff --git a/lib/bolt/transport/winrm/connection.rb b/lib/bolt/transport/winrm/connection.rb
index c81332a915..b7b0d2ca4c 100644
--- a/lib/bolt/transport/winrm/connection.rb
+++ b/lib/bolt/transport/winrm/connection.rb
@@ -148,6 +148,7 @@ def mkdirs(dirs)
         end
 
         def write_remote_file(source, destination)
+          @logger.debug { "Uploading #{source}, to #{destination}" }
           if target.options['file-protocol'] == 'smb'
             write_remote_file_smb(source, destination)
           else