rails_console_ai 0.22.0 → 0.23.0

data/lib/rails_console_ai/conversation_engine.rb

@@ -3,9 +3,10 @@ module RailsConsoleAi
     attr_reader :history, :total_input_tokens, :total_output_tokens,
                 :interactive_session_id, :session_name
 
-    RECENT_OUTPUTS_TO_KEEP = 2
     LARGE_OUTPUT_THRESHOLD = 10_000      # chars — truncate tool results larger than this immediately
     LARGE_OUTPUT_PREVIEW_CHARS = 8_000   # chars — how much of the output the LLM sees upfront
+    LOOP_WARN_THRESHOLD = 3              # same tool+args repeated → inject warning
+    LOOP_BREAK_THRESHOLD = 5             # same tool+args repeated → break loop
 
     def initialize(binding_context:, channel:, slack_thread_ts: nil, slack_channel_name: nil)
       @binding_context = binding_context
@@ -30,6 +31,7 @@ module RailsConsoleAi
       @last_interactive_executed = false
       @compact_warned = false
       @prior_duration_ms = 0
+      @expanded_output_ids = Set.new
     end
 
     # --- Public API for channels ---
@@ -47,7 +49,7 @@ module RailsConsoleAi
           conversation << { role: :assistant, content: @_last_result_text }
           conversation << { role: :user, content: error_msg }
 
-          @channel.display_dim("  Attempting to fix...")
+          @channel.display_dim("  Ran into an issue, trying a different approach...")
           exec_result, code, executed = one_shot_round(conversation)
         end
 
@@ -112,7 +114,7 @@ module RailsConsoleAi
 
       status = send_and_execute
       if status == :error
-        @channel.display_dim("  Attempting to fix...")
+        @channel.display_dim("  Ran into an issue, trying a different approach...")
         send_and_execute
       end
     end
@@ -235,7 +237,7 @@ module RailsConsoleAi
     end
 
     def execute_direct(raw_code)
-      exec_result = @executor.execute(raw_code)
+      exec_result = @executor.execute_unsafe(raw_code)
 
       output_parts = []
       output_parts << "Output:\n#{@executor.last_output.strip}" if @executor.last_output && !@executor.last_output.strip.empty?
@@ -244,12 +246,11 @@ module RailsConsoleAi
       result_str = output_parts.join("\n\n")
 
       context_msg = "User directly executed code: `#{raw_code}`"
+      output_id = @executor.store_output(result_str)
       if result_str.length > LARGE_OUTPUT_THRESHOLD
-        output_id = @executor.store_output(result_str)
         preview = result_str[0, LARGE_OUTPUT_PREVIEW_CHARS]
         context_msg += "\n#{preview}\n\n[Output truncated at #{LARGE_OUTPUT_PREVIEW_CHARS} of #{result_str.length} chars — use recall_output tool with id #{output_id} to retrieve the full output]"
       elsif !output_parts.empty?
-        output_id = @executor.store_output(result_str)
         context_msg += "\n#{result_str}"
       end
       @history << { role: :user, content: context_msg, output_id: output_id }
@@ -263,7 +264,7 @@ module RailsConsoleAi
 
     def send_and_execute
       begin
-        result, tool_messages = send_query(nil, conversation: @history)
+        result, tool_messages, last_llm_stats = send_query(nil, conversation: @history)
       rescue Providers::ProviderError => e
         if e.message.include?("prompt is too long") && @history.length >= 6
           @channel.display_warning("  Context limit reached. Run /compact to reduce context size, then try again.")
@@ -284,7 +285,15 @@ module RailsConsoleAi
       log_interactive_turn
 
       @history.concat(tool_messages) if tool_messages && !tool_messages.empty?
-      @history << { role: :assistant, content: result.text }
+      # Only add the final assistant text when the LLM gave a final response (end_turn).
+      # For tool_use results, the assistant message is already in tool_messages via
+      # format_assistant_message, so adding result.text again would duplicate it —
+      # and if the text is empty, Bedrock rejects the empty content array.
+      unless result.tool_use?
+        entry = { role: :assistant, content: result.text }
+        entry[:llm_stats] = last_llm_stats if last_llm_stats
+        @history << entry
+      end
 
       return :no_code unless code && !code.strip.empty?
       return :cancelled if @channel.cancelled?
@@ -413,15 +422,23 @@ module RailsConsoleAi
         return
       end
 
-      trimmed = trim_old_outputs(@history)
-      stdout.puts "\e[36m  Conversation (#{trimmed.length} messages, as sent to LLM):\e[0m"
-      trimmed.each_with_index do |msg, i|
-        role = msg[:role].to_s
-        content = msg[:content].to_s
-        label = role == 'user' ? "\e[33m[user]\e[0m" : "\e[36m[assistant]\e[0m"
-        stdout.puts "#{label} #{content}"
-        stdout.puts if i < trimmed.length - 1
-      end
+      messages = trim_large_outputs(@history)
+      system_prompt = context
+      require 'rails_console_ai/tools/registry'
+      tools = Tools::Registry.new(executor: @executor, channel: @channel) rescue nil
+      opts = { io: stdout, prefix: "  ", d: "\e[2m", r: "\e[0m" }
+      conversation_summary(messages, system_prompt, tools, **opts)
+      conversation_messages(messages, **opts)
+    end
+
+    def display_conversation_to(io)
+      messages = trim_large_outputs(@history)
+      system_prompt = context
+      require 'rails_console_ai/tools/registry'
+      tools = Tools::Registry.new(executor: @executor, channel: @channel) rescue nil
+      opts = { io: io, prefix: "", d: "", r: "" }
+      conversation_summary(messages, system_prompt, tools, **opts)
+      conversation_messages(messages, **opts)
     end
 
     def context
@@ -710,8 +727,8 @@ module RailsConsoleAi
 
         EXPLORATION STRATEGY — be efficient to avoid timeouts:
         1. Start with list_models to see all models and their associations
-        2. Pick the 5-8 CORE models and call describe_model on those only
-        3. Call describe_table on only 3-5 key tables (skip tables whose models already told you enough)
+        2. Pick the 5-8 CORE models and call describe_model on those only (it includes columns, indexes, associations, validations)
+        3. Call describe_table only for tables that have NO corresponding model (join tables, legacy tables, etc.)
         4. Use search_code sparingly — only for specific patterns you suspect (sharding, STI, concerns)
         5. Use read_file only when you need to understand a specific pattern (read small sections, not whole files)
         6. Do NOT exhaustively describe every table or model — focus on what's important
@@ -751,7 +768,7 @@ module RailsConsoleAi
                    [{ role: :user, content: query }]
                  end
 
-      messages = trim_old_outputs(messages) if conversation
+      messages = trim_large_outputs(messages) if conversation
 
       send_query_with_tools(messages)
     end
@@ -769,6 +786,7 @@ module RailsConsoleAi
       last_tool_names = []
 
       exhausted = false
+      tool_call_counts = Hash.new(0)
 
       max_rounds.times do |round|
         if @channel.cancelled?
@@ -787,9 +805,9 @@ module RailsConsoleAi
           @channel.display_dim("  #{llm_status(round, messages, total_input, last_thinking, last_tool_names)}")
         end
 
-        # Trim old tool outputs between rounds to prevent context explosion.
+        # Trim large tool outputs between rounds to prevent context explosion.
         # The LLM can still retrieve omitted outputs via recall_output.
-        messages = trim_old_outputs(messages) if round > 0
+        messages = trim_large_outputs(messages) if round > 0
 
         if RailsConsoleAi.configuration.debug
           debug_pre_call(round, messages, active_system_prompt, tools, total_input, total_output)
@@ -816,6 +834,7 @@ module RailsConsoleAi
         last_thinking = (result.text && !result.text.strip.empty?) ? result.text.strip : nil
 
         assistant_msg = provider.format_assistant_message(result)
+        assistant_msg[:llm_stats] = format_llm_stats(result)
         messages << assistant_msg
         new_messages << assistant_msg
 
@@ -844,12 +863,13 @@ module RailsConsoleAi
             next
           end
 
+          # Display any pending LLM text before executing the tool
+          if last_thinking
+            last_thinking.split("\n").each { |line| @channel.display_dim("  #{line}") }
+            last_thinking = nil
+          end
+
           if tc[:name] == 'ask_user' || tc[:name] == 'execute_plan'
-            # Display any pending LLM text before prompting the user
-            if last_thinking
-              last_thinking.split("\n").each { |line| @channel.display_dim("  #{line}") }
-              last_thinking = nil
-            end
             tool_result = tools.execute(tc[:name], tc[:arguments])
           else
             args_display = format_tool_args(tc[:name], tc[:arguments])
@@ -868,20 +888,35 @@ module RailsConsoleAi
 
           tool_msg = provider.format_tool_result(tc[:id], tool_result)
           full_text = tool_result.to_s
+          output_id = @executor.store_output(full_text)
+          tool_msg[:output_id] = output_id
           if full_text.length > LARGE_OUTPUT_THRESHOLD
-            output_id = @executor.store_output(full_text)
-            tool_msg[:output_id] = output_id
             truncated = full_text[0, LARGE_OUTPUT_PREVIEW_CHARS]
             truncated += "\n\n[Output truncated at #{LARGE_OUTPUT_PREVIEW_CHARS} of #{full_text.length} chars — use recall_output tool with id #{output_id} to retrieve the full output]"
             tool_msg = provider.format_tool_result(tc[:id], truncated)
             tool_msg[:output_id] = output_id
-          elsif full_text.length > 200
-            tool_msg[:output_id] = @executor.store_output(full_text)
           end
+          tool_msg[:do_not_trim] = true if %w[recall_memory recall_memories activate_skill
+                                                describe_model describe_table list_models list_tables].include?(tc[:name])
           messages << tool_msg
           new_messages << tool_msg
         end
 
+        # Loop detection: track repeated identical tool calls
+        result.tool_calls.each do |tc|
+          key = "#{tc[:name]}:#{tc[:arguments].to_json}"
+          tool_call_counts[key] += 1
+
+          if tool_call_counts[key] >= LOOP_BREAK_THRESHOLD
+            @channel.display_dim("  Loop detected: #{tc[:name]} called #{tool_call_counts[key]} times with same args — stopping.")
+            exhausted = true
+          elsif tool_call_counts[key] >= LOOP_WARN_THRESHOLD
+            @channel.display_dim("  Warning: #{tc[:name]} called #{tool_call_counts[key]} times with same args — consider a different approach.")
+            messages << { role: :user, content: "You are repeating the same tool call (#{tc[:name]}) with the same arguments. This is not making progress. Try a different approach or provide your answer now." }
+          end
+        end
+        break if exhausted
+
         # If the user declined execution, don't call the LLM again —
         # just return to the prompt so they can correct their request.
         break if @executor.last_cancelled?
@@ -889,10 +924,6 @@ module RailsConsoleAi
         exhausted = true if round == max_rounds - 1
       end
 
-      # Re-truncate any outputs that were expanded for the LLM — the LLM has
-      # seen them and responded, so collapse back to save context on future calls.
-      re_truncate_expanded(messages)
-
       if exhausted
         $stdout.puts "\e[33m  Hit tool round limit (#{max_rounds}). Forcing final answer. Increase with: RailsConsoleAi.configure { |c| c.max_tool_rounds = 200 }\e[0m"
         messages << { role: :user, content: "You've used all available tool rounds. Please provide your best answer now based on what you've learned so far." }
@@ -901,13 +932,14 @@ module RailsConsoleAi
         total_output += result.output_tokens || 0
       end
 
+      last_llm_stats = result ? format_llm_stats(result) : nil
       final_result = Providers::ChatResult.new(
         text: result ? result.text : '',
         input_tokens: total_input,
         output_tokens: total_output,
         stop_reason: result ? result.stop_reason : :end_turn
       )
-      [final_result, new_messages]
+      [final_result, new_messages, last_llm_stats]
     end
 
     def track_usage(result)
@@ -928,6 +960,9 @@ module RailsConsoleAi
 
       parts = []
       parts << "in: #{input}" if input
+      cache_r = result.cache_read_input_tokens || 0
+      cache_w = result.cache_write_input_tokens || 0
+      parts << "cache r: #{cache_r} w: #{cache_w}" if cache_r > 0 || cache_w > 0
       parts << "out: #{output}" if output
       parts << "total: #{result.total_tokens}"
 
@@ -989,8 +1024,11 @@ module RailsConsoleAi
       when 'list_files'      then args['directory'] ? "(\"#{args['directory']}\")" : ''
       when 'save_memory'     then "(\"#{args['name']}\")"
       when 'delete_memory'   then "(\"#{args['name']}\")"
+      when 'recall_memory'   then "(\"#{args['name']}\")"
       when 'recall_memories' then args['query'] ? "(\"#{args['query']}\")" : ''
       when 'activate_skill' then "(\"#{args['name']}\")"
+      when 'save_skill'     then "(\"#{args['name']}\")"
+      when 'delete_skill'   then "(\"#{args['name']}\")"
       when 'recall_output'   then "(#{args['id']})"
       when 'execute_plan'
         steps = args['steps']
@@ -1013,8 +1051,10 @@ module RailsConsoleAi
         "#{result.scan(/^\s{2}\S/).length} columns"
       when 'describe_model'
         parts = []
+        col_count = result.scan(/^\s{2}\S+:\S+/).length
         assoc_count = result.scan(/^\s{2}(has_many|has_one|belongs_to|has_and_belongs_to_many)/).length
         val_count = result.scan(/^\s{2}(presence|uniqueness|format|length|numericality|inclusion|exclusion|confirmation|acceptance)/).length
+        parts << "#{col_count} columns" if col_count > 0
         parts << "#{assoc_count} associations" if assoc_count > 0
         parts << "#{val_count} validations" if val_count > 0
         parts.empty? ? truncate(result, 80) : parts.join(', ')
@@ -1034,9 +1074,27 @@ module RailsConsoleAi
         (result.start_with?('Memory saved') || result.start_with?('Memory updated')) ? result : truncate(result, 80)
       when 'delete_memory'
         result.start_with?('Memory deleted') ? result : truncate(result, 80)
+      when 'save_skill'
+        (result.start_with?('Skill created') || result.start_with?('Skill updated')) ? result : truncate(result, 80)
+      when 'delete_skill'
+        result.start_with?('Skill deleted') ? result : truncate(result, 80)
+      when 'recall_memory'
+        if result.start_with?('No memory found')
+          result
+        else
+          name = result[/\A\*\*(.+?)\*\*/, 1]
+          name ? "loaded: #{name}" : truncate(result, 80)
+        end
       when 'recall_memories'
-        chunks = result.split("\n\n")
-        chunks.length > 1 ? "#{chunks.length} memories found" : truncate(result, 80)
+        chunks = result.split("\n\n---\n\n")
+        names = chunks.map { |c| c[/\A\*\*(.+?)\*\*/, 1] }.compact
+        if names.length > 1
+          "#{names.length} memories found: #{names.join(', ')}"
+        elsif names.length == 1
+          "1 memory found: #{names.first}"
+        else
+          truncate(result, 80)
+        end
       when 'execute_plan'
         steps_done = result.scan(/^Step \d+/).length
         steps_done > 0 ? "#{steps_done} steps executed" : truncate(result, 80)
@@ -1062,36 +1120,103 @@ module RailsConsoleAi
       status
     end
 
+    # Provider-agnostic block detection helpers.
+    # Anthropic uses string keys: { 'type' => 'tool_result', ... }
+    # Bedrock uses symbol keys:   { tool_result: { ... } }
+    def tool_result_block?(block)
+      return false unless block.is_a?(Hash)
+      block['type'] == 'tool_result' || block.key?(:tool_result)
+    end
+
+    def tool_use_block?(block)
+      return false unless block.is_a?(Hash)
+      block['type'] == 'tool_use' || block.key?(:tool_use)
+    end
+
+    def tool_result_content(block)
+      if block['type'] == 'tool_result'
+        block['content'].to_s
+      elsif block.key?(:tool_result)
+        content = block[:tool_result][:content]
+        content.is_a?(Array) ? content.map { |c| c[:text].to_s }.join : content.to_s
+      else
+        ''
+      end
+    end
+
+    def tool_use_name(block)
+      if block['type'] == 'tool_use'
+        block['name']
+      elsif block.key?(:tool_use)
+        block[:tool_use][:name]
+      end
+    end
+
     def debug_pre_call(round, messages, system_prompt, tools, total_input, total_output)
       d = "\e[35m"
       r = "\e[0m"
+      $stderr.puts "#{d}[debug] ── LLM call ##{round + 1} ──#{r}"
+      conversation_summary(messages, system_prompt, tools, io: $stderr, prefix: "[debug]   ", d: d, r: r)
+      if total_input > 0 || total_output > 0
+        $stderr.puts "#{d}[debug]   tokens so far: in: #{format_tokens(total_input)} | out: #{format_tokens(total_output)}#{r}"
+      end
+      conversation_messages(messages, io: $stderr, prefix: "[debug]   ", d: d, r: r, show_pending: true)
+    end
 
+    def conversation_summary(messages, system_prompt, tools, io:, prefix:, d:, r:)
       user_msgs = 0; assistant_msgs = 0; tool_result_msgs = 0; tool_use_msgs = 0
-      output_msgs = 0; omitted_msgs = 0
+      output_msgs = 0; omitted_msgs = 0; expanded_msgs = 0
       total_content_chars = system_prompt.to_s.length
 
       messages.each do |msg|
         content_str = msg[:content].is_a?(Array) ? msg[:content].to_s : msg[:content].to_s
         total_content_chars += content_str.length
+        is_expanded = msg[:expanded] || (msg[:output_id] && @expanded_output_ids.include?(msg[:output_id]))
 
         role = msg[:role].to_s
         if role == 'tool'
           tool_result_msgs += 1
         elsif msg[:content].is_a?(Array)
+          has_tool_block = false
           msg[:content].each do |block|
             next unless block.is_a?(Hash)
-            if block['type'] == 'tool_result'
+            if tool_result_block?(block)
               tool_result_msgs += 1
-              omitted_msgs += 1 if block['content'].to_s.include?('Output omitted')
-            elsif block['type'] == 'tool_use'
+              has_tool_block = true
+              if is_expanded
+                expanded_msgs += 1
+              elsif tool_result_content(block).include?('Output omitted')
+                omitted_msgs += 1
+              end
+            elsif tool_use_block?(block)
               tool_use_msgs += 1
+              has_tool_block = true
+            end
+          end
+          unless has_tool_block
+            if role == 'user'
+              user_msgs += 1
+              if content_str.include?('Code was executed') || content_str.include?('directly executed code')
+                output_msgs += 1
+                if is_expanded
+                  expanded_msgs += 1
+                elsif content_str.include?('Output omitted')
+                  omitted_msgs += 1
+                end
+              end
+            elsif role == 'assistant'
+              assistant_msgs += 1
             end
           end
         elsif role == 'user'
           user_msgs += 1
           if content_str.include?('Code was executed') || content_str.include?('directly executed code')
             output_msgs += 1
-            omitted_msgs += 1 if content_str.include?('Output omitted')
+            if is_expanded
+              expanded_msgs += 1
+            elsif content_str.include?('Output omitted')
+              omitted_msgs += 1
+            end
           end
         elsif role == 'assistant'
           assistant_msgs += 1
@@ -1100,15 +1225,108 @@ module RailsConsoleAi
 
       tool_count = tools.respond_to?(:definitions) ? tools.definitions.length : 0
 
-      $stderr.puts "#{d}[debug] ── LLM call ##{round + 1} ──#{r}"
-      $stderr.puts "#{d}[debug]   system prompt: #{format_tokens(system_prompt.to_s.length)} chars#{r}"
-      $stderr.puts "#{d}[debug]   messages: #{messages.length} (#{user_msgs} user, #{assistant_msgs} assistant, #{tool_result_msgs} tool results, #{tool_use_msgs} tool calls)#{r}"
-      $stderr.puts "#{d}[debug]   execution outputs: #{output_msgs} (#{omitted_msgs} omitted)#{r}" if output_msgs > 0 || omitted_msgs > 0
-      $stderr.puts "#{d}[debug]   tools provided: #{tool_count}#{r}"
-      $stderr.puts "#{d}[debug]   est. content size: #{format_tokens(total_content_chars)} chars#{r}"
-      if total_input > 0 || total_output > 0
-        $stderr.puts "#{d}[debug]   tokens so far: in: #{format_tokens(total_input)} | out: #{format_tokens(total_output)}#{r}"
+      io.puts "#{d}#{prefix}system prompt: #{format_tokens(system_prompt.to_s.length)} chars#{r}"
+      io.puts "#{d}#{prefix}messages: #{messages.length} (#{user_msgs} user, #{assistant_msgs} assistant, #{tool_result_msgs} tool results, #{tool_use_msgs} tool calls)#{r}"
+      if output_msgs > 0 || omitted_msgs > 0 || expanded_msgs > 0
+        detail_parts = []
+        detail_parts << "#{omitted_msgs} omitted" if omitted_msgs > 0
+        detail_parts << "#{expanded_msgs} expanded" if expanded_msgs > 0
+        io.puts "#{d}#{prefix}execution outputs: #{output_msgs} (#{detail_parts.join(', ')})#{r}"
       end
+      io.puts "#{d}#{prefix}tools provided: #{tool_count}#{r}"
+      io.puts "#{d}#{prefix}est. content size: #{format_tokens(total_content_chars)} chars#{r}"
+    end
+
+    def conversation_messages(messages, io:, prefix:, d:, r:, show_pending: false)
+      io.puts "#{d}#{prefix}conversation:#{r}"
+      llm_call = 0
+      messages.each_with_index do |msg, i|
+        role = msg[:role].to_s
+        parts = []
+        display_role = role
+        is_assistant = role == 'assistant' || (msg[:content].is_a?(Array) && msg[:content].any? { |b| b.is_a?(Hash) && tool_use_block?(b) })
+
+        if is_assistant
+          llm_call += 1
+          stats = msg[:llm_stats] ? " → #{msg[:llm_stats]}" : ""
+          io.puts "#{d}#{prefix}  ── LLM call ##{llm_call}#{stats} ──#{r}"
+        end
+
+        if role == 'tool'
+          display_role = 'tool_result'
+          text = msg[:content].to_s
+          flags = debug_output_flags(text, msg)
+          flag_str = flags.any? ? ", #{flags.join(', ')}" : ""
+          parts << "#{text.length} chars#{flag_str}"
+        elsif msg[:content].is_a?(Array)
+          has_tool_result = false
+          has_tool_use = false
+          msg[:content].each do |block|
+            next unless block.is_a?(Hash)
+            if tool_result_block?(block)
+              has_tool_result = true
+              content = tool_result_content(block)
+              flags = debug_output_flags(content, msg)
+              flag_str = flags.any? ? ", #{flags.join(', ')}" : ""
+              parts << "#{content.length} chars#{flag_str}"
+            elsif tool_use_block?(block)
+              has_tool_use = true
+              parts << "tool_use: #{tool_use_name(block)}"
+            elsif block['type'] == 'text' || block.key?(:text)
+              text = block['text'] || block[:text]
+              parts << "text(#{text.to_s.length} chars)" if text.to_s.length > 0
+            end
+          end
+          display_role = 'tool_result' if has_tool_result && !has_tool_use
+          display_role = 'assistant' if has_tool_use && !has_tool_result
+        else
+          text = msg[:content].to_s
+          preview = text.length > 60 ? text[0, 57] + "..." : text
+          preview = preview.gsub("\n", "\\n")
+          flags = debug_output_flags(text, msg)
+          flag_str = flags.any? ? " (#{flags.join(', ')})" : ""
+          parts << "\"#{preview}\" #{text.length} chars#{flag_str}"
+        end
+
+        io.puts "#{d}#{prefix}  ##{i} #{display_role}: [#{parts.join(', ')}]#{r}"
+      end
+      if show_pending
+        llm_call += 1
+        io.puts "#{d}#{prefix}  ── LLM call ##{llm_call} (pending) ──#{r}"
+      end
+    end
+
+    def format_llm_stats(result)
+      parts = ["in: #{format_tokens(result.input_tokens || 0)}"]
+      parts << "out: #{format_tokens(result.output_tokens || 0)}"
+      cache_r = result.cache_read_input_tokens || 0
+      cache_w = result.cache_write_input_tokens || 0
+      parts << "cache r: #{format_tokens(cache_r)} w: #{format_tokens(cache_w)}" if cache_r > 0 || cache_w > 0
+      model = effective_model
+      pricing = Configuration::PRICING[model]
+      if pricing
+        cost = ((result.input_tokens || 0) * pricing[:input]) + ((result.output_tokens || 0) * pricing[:output])
+        if (cache_r > 0 || cache_w > 0) && pricing[:cache_read]
+          cost -= cache_r * pricing[:input]
+          cost += cache_r * pricing[:cache_read]
+          cost += cache_w * (pricing[:cache_write] - pricing[:input])
+        end
+        parts << "~$#{'%.4f' % cost}"
+      end
+      parts.join(' | ')
+    end
+
+    def debug_output_flags(content_text, msg)
+      flags = []
+      flags << "output ##{msg[:output_id]}" if msg[:output_id]
+      if msg[:expanded] || (msg[:output_id] && @expanded_output_ids.include?(msg[:output_id]))
+        flags << "expanded"
+      elsif content_text.include?('Output omitted')
+        flags << "omitted"
+      elsif (m = content_text.match(/Output truncated at (\S+) of (\S+) chars/))
+        flags << "truncated #{m[2]}→#{m[1]}"
+      end
+      flags
     end
 
     def debug_post_call(round, result, total_input, total_output)
@@ -1135,9 +1353,9 @@ module RailsConsoleAi
         end
         session_cost = (total_input * pricing[:input]) + (total_output * pricing[:output])
         parts << "~$#{'%.4f' % cost}"
-        $stderr.puts "#{d}[debug]   ← response: #{parts.join(' | ')}  (session: ~$#{'%.4f' % session_cost})#{r}"
+        $stderr.puts "\n#{d}[debug]   ← response: #{parts.join(' | ')}  (session: ~$#{'%.4f' % session_cost})#{r}"
       else
-        $stderr.puts "#{d}[debug]   ← response: #{parts.join(' | ')}#{r}"
+        $stderr.puts "\n#{d}[debug]   ← response: #{parts.join(' | ')}#{r}"
       end
 
       if result.tool_use?
@@ -1150,20 +1368,18 @@ module RailsConsoleAi
 
     # --- Conversation context management ---
 
-    def trim_old_outputs(messages)
-      output_indices = messages.each_with_index
-                               .select { |m, _| m[:output_id] }
-                               .map { |_, i| i }
-
-      return messages if output_indices.length <= RECENT_OUTPUTS_TO_KEEP
-
-      trim_indices = output_indices[0..-(RECENT_OUTPUTS_TO_KEEP + 1)]
-      messages.each_with_index.map do |msg, i|
-        if trim_indices.include?(i)
-          trim_message(msg)
-        else
-          msg
+    def trim_large_outputs(messages)
+      messages.map do |msg|
+        next msg unless msg[:output_id] && !msg[:do_not_trim]
+        # Re-expand messages that were expanded in a prior turn but lost content
+        # (because trim_message creates new hashes, disconnecting from @history)
+        if @expanded_output_ids.include?(msg[:output_id]) && !msg[:expanded]
+          expand_message_in_place(msg)
         end
+        next msg if msg[:expanded]
+        stored = @executor.recall_output(msg[:output_id])
+        next msg unless stored && stored.length > LARGE_OUTPUT_THRESHOLD
+        trim_message(msg)
       end
     end
 
@@ -1172,8 +1388,14 @@ module RailsConsoleAi
 
       if msg[:content].is_a?(Array)
         trimmed_content = msg[:content].map do |block|
-          if block.is_a?(Hash) && block['type'] == 'tool_result'
-            block.merge('content' => ref)
+          if block.is_a?(Hash) && tool_result_block?(block)
+            if block.key?(:tool_result)
+              # Bedrock format
+              block.merge(tool_result: block[:tool_result].merge(content: [{ text: ref }]))
+            else
+              # Anthropic format
+              block.merge('content' => ref)
+            end
           else
             block
           end
@@ -1191,40 +1413,40 @@ module RailsConsoleAi
       expanded = []
       messages.each do |msg|
         next unless msg[:output_id] && ids.include?(msg[:output_id])
-        full_output = @executor.recall_output(msg[:output_id])
-        next unless full_output
-        # Save original content so re_truncate_expanded can restore it
-        msg[:pre_expand_content] = msg[:content]
-        # Replace content with full output (handle Anthropic, OpenAI, and user message formats)
-        if msg[:content].is_a?(Array)
-          msg[:content] = msg[:content].map do |block|
-            if block.is_a?(Hash) && block['type'] == 'tool_result'
-              block.merge('content' => full_output)
-            else
-              block
-            end
-          end
-        elsif msg[:role].to_s == 'tool'
-          msg[:content] = full_output
-        else
-          # User messages (e.g., direct execution) — preserve first line, replace rest
-          first_line = msg[:content].to_s.lines.first&.chomp || ''
-          msg[:content] = "#{first_line}\n#{full_output}"
-        end
-        msg[:expanded] = true
+        next unless expand_message_in_place(msg)
         expanded << msg[:output_id]
       end
       expanded
     end
 
-    # Restore messages that were temporarily expanded back to their original
-    # (preview/truncated) content. Called after the LLM has seen the expanded
-    # content and responded.
-    def re_truncate_expanded(messages)
-      messages.each do |msg|
-        next unless msg.delete(:expanded)
-        msg[:content] = msg.delete(:pre_expand_content)
+    def expand_message_in_place(msg)
+      full_output = @executor.recall_output(msg[:output_id])
+      return false unless full_output
+      # Replace content with full output (handle Anthropic, Bedrock, and user message formats)
+      if msg[:content].is_a?(Array)
+        msg[:content] = msg[:content].map do |block|
+          if block.is_a?(Hash) && tool_result_block?(block)
+            if block.key?(:tool_result)
+              # Bedrock format
+              block.merge(tool_result: block[:tool_result].merge(content: [{ text: full_output }]))
+            else
+              # Anthropic format
+              block.merge('content' => full_output)
+            end
+          else
+            block
+          end
+        end
+      elsif msg[:role].to_s == 'tool'
+        msg[:content] = full_output
+      else
+        # User messages (e.g., direct execution) — preserve first line, replace rest
+        first_line = msg[:content].to_s.lines.first&.chomp || ''
+        msg[:content] = "#{first_line}\n#{full_output}"
       end
+      msg[:expanded] = true
+      @expanded_output_ids.add(msg[:output_id])
+      true
     end
 
     def extract_executed_code(history)
@@ -1246,11 +1468,11 @@ module RailsConsoleAi
 
         if msg[:role].to_s == 'assistant' && msg[:content].is_a?(Array)
           msg[:content].each do |block|
-            next unless block.is_a?(Hash) && block['type'] == 'tool_use' && block['name'] == 'execute_plan'
-            input = block['input'] || {}
+            next unless block.is_a?(Hash) && tool_use_block?(block) && tool_use_name(block) == 'execute_plan'
+            input = block['input'] || block.dig(:tool_use, :input) || {}
             steps = input['steps'] || []
 
-            tool_id = block['id']
+            tool_id = block['id'] || block.dig(:tool_use, :tool_use_id)
             result_msg = find_tool_result(history, tool_id)
             next unless result_msg
 
@@ -1274,14 +1496,15 @@ module RailsConsoleAi
 
     def find_tool_result(history, tool_id)
       history.each do |msg|
+        if msg[:role].to_s == 'tool' && msg[:tool_call_id] == tool_id
+          return msg[:content]
+        end
         next unless msg[:content].is_a?(Array)
         msg[:content].each do |block|
           next unless block.is_a?(Hash)
-          if block['type'] == 'tool_result' && block['tool_use_id'] == tool_id
-            return block['content']
-          end
-          if msg[:role].to_s == 'tool' && msg[:tool_call_id] == tool_id
-            return msg[:content]
+          if tool_result_block?(block)
+            block_tool_id = block['tool_use_id'] || block.dig(:tool_result, :tool_use_id)
+            return tool_result_content(block) if block_tool_id == tool_id
           end
         end
       end