diff --git a/lib/roast/workflow/base_workflow.rb b/lib/roast/workflow/base_workflow.rb
index 5c69818..eeb48c8 100644
--- a/lib/roast/workflow/base_workflow.rb
+++ b/lib/roast/workflow/base_workflow.rb
@@ -34,7 +34,11 @@ def initialize(file = nil, name: nil, context_path: nil, resource: nil, session_
         @session_name = session_name || @name
         @session_timestamp = nil
         @configuration = configuration
-        transcript << { system: read_sidecar_prompt }
+        read_sidecar_prompt.then do |prompt|
+          next unless prompt
+
+          transcript << { system: prompt }
+        end
         Roast::Tools.setup_interrupt_handler(transcript)
         Roast::Tools.setup_exit_handler(self)
       end
diff --git a/lib/roast/workflow/session_manager.rb b/lib/roast/workflow/session_manager.rb
index 9978045..8ab8b8c 100644
--- a/lib/roast/workflow/session_manager.rb
+++ b/lib/roast/workflow/session_manager.rb
@@ -7,6 +7,8 @@ module Roast
   module Workflow
     # Manages session creation, timestamping, and directory management
     class SessionManager
+      TARGETLESS_FILE_PATH = "notarget"
+
       def initialize
         @session_mutex = Mutex.new
         @session_timestamps = {}
@@ -66,6 +68,7 @@ def create_new_session(workflow_id)
       private
 
       def workflow_directory(session_name, file_path)
+        file_path ||= TARGETLESS_FILE_PATH
         workflow_dir_name = session_name.parameterize.underscore
         file_id = Digest::MD5.hexdigest(file_path)
         file_basename = File.basename(file_path).parameterize.underscore