Improved challenge prompt and instructions

config.py

@@ -14,7 +14,7 @@ import os
 # These values are used in server responses and for tracking releases
 # IMPORTANT: This is the single source of truth for version and author info
 # Semantic versioning: MAJOR.MINOR.PATCH
-__version__ = "5.8.0"
+__version__ = "5.8.1"
 # Last update date in ISO format
 __updated__ = "2025-06-30"
 # Primary maintainer

tests/test_challenge.py

@@ -25,8 +25,8 @@ class TestChallengeTool:
         """Test that tool metadata matches requirements"""
         assert self.tool.get_name() == "challenge"
         assert "CRITICAL CHALLENGE PROMPT" in self.tool.get_description()
-        assert "challenge it thoughtfully" in self.tool.get_description()
+        assert "critical examination" in self.tool.get_description()
-        assert "agreeing by default" in self.tool.get_description()
+        assert "default agreement" in self.tool.get_description()
         assert self.tool.get_default_temperature() == 0.2  # TEMPERATURE_ANALYTICAL
 
     def test_requires_model(self):
@@ -100,11 +100,11 @@ class TestChallengeTool:
 
         # Check that the challenge prompt contains critical thinking instructions
         challenge_prompt = response_data["challenge_prompt"]
-        assert "CHALLENGE THIS STATEMENT - Do not automatically agree" in challenge_prompt
+        assert "CRITICAL REASSESSMENT – Do not automatically agree" in challenge_prompt
-        assert "Is this actually correct? Check carefully" in challenge_prompt
+        assert "Carefully evaluate the statement above" in challenge_prompt
         assert response_data["original_statement"] in challenge_prompt
-        assert "you must say so" in challenge_prompt
+        assert "flaws, gaps, or misleading points" in challenge_prompt
-        assert "Provide your honest assessment, not automatic agreement" in challenge_prompt
+        assert "thoughtful analysis" in challenge_prompt
 
     @pytest.mark.asyncio
     async def test_execute_error_handling(self):
@@ -124,11 +124,11 @@ class TestChallengeTool:
         wrapped = self.tool._wrap_prompt_for_challenge(original_prompt)
 
         # Check structure
-        assert "CHALLENGE THIS STATEMENT - Do not automatically agree" in wrapped
+        assert "CRITICAL REASSESSMENT – Do not automatically agree" in wrapped
-        assert "Is this actually correct? Check carefully" in wrapped
+        assert "Carefully evaluate the statement above" in wrapped
         assert f'"{original_prompt}"' in wrapped
-        assert "you must say so" in wrapped
+        assert "flaws, gaps, or misleading points" in wrapped
-        assert "Provide your honest assessment, not automatic agreement" in wrapped
+        assert "thoughtful analysis" in wrapped
 
     def test_multiple_prompts(self):
         """Test that tool handles various types of prompts correctly"""
@@ -146,7 +146,7 @@ class TestChallengeTool:
 
             # Each wrapped prompt should contain the original
             assert prompt in wrapped
-            assert "CHALLENGE THIS STATEMENT" in wrapped
+            assert "CRITICAL REASSESSMENT" in wrapped
 
     def test_tool_fields(self):
         """Test tool-specific field definitions"""
@@ -155,7 +155,7 @@ class TestChallengeTool:
         assert "prompt" in fields
         assert fields["prompt"]["type"] == "string"
         assert "statement" in fields["prompt"]["description"]
-        assert "challenge" in fields["prompt"]["description"]
+        assert "critically evaluate" in fields["prompt"]["description"]
 
     def test_required_fields_list(self):
         """Test required fields list"""

tools/challenge.py

@@ -23,8 +23,10 @@ from .simple.base import SimpleTool
 # Field descriptions for the Challenge tool
 CHALLENGE_FIELD_DESCRIPTIONS = {
     "prompt": (
-        "The statement, question, or assertion the user wants to challenge critically. "
+        "The original statement, question, or assertion the user intends to critically evaluate. "
-        "This may be a claim, suggestion, or idea that requires thoughtful reconsideration, not automatic agreement."
+        "This may be a claim, suggestion, or idea that requires thoughtful analysis, not automatic agreement. "
+        "MANDATORY: Do NOT rephrase or paraphrase. Submit the statement EXACTLY AS PROVIDED, as it will be used "
+        "verbatim in a new prompt."
     ),
 }
 
@@ -53,11 +55,11 @@ class ChallengeTool(SimpleTool):
 
     def get_description(self) -> str:
         return (
-            "CRITICAL CHALLENGE PROMPT – Use this to frame your statement in a way that prompts "
+            "CRITICAL CHALLENGE PROMPT – Use this to explicitly frame your input for critical examination. "
-            "the CLI agent to challenge it thoughtfully instead of agreeing by default. Ideal for "
+            "Instead of default agreement, the CLI agent will be instructed to analyze, question, and, if needed, "
-            "challenging assumptions, validating ideas, and seeking honest, analytical feedback as part of an ongoing "
+            "disagree with your statement. Ideal for validating assumptions, pressure-testing ideas, and eliciting "
-            "task. The tool wraps your input with instructions explicitly telling the agent to think critically "
+            "honest feedback during complex workflows. The tool ensures your input is wrapped with clear guidance "
-            "and disagree if warranted."
+            "to encourage thoughtful scrutiny."
         )
 
     def get_system_prompt(self) -> str:
@@ -133,8 +135,9 @@ class ChallengeTool(SimpleTool):
                 "challenge_prompt": wrapped_prompt,
                 "instructions": (
                     "Present the challenge_prompt to yourself and follow its instructions. "
-                    "Challenge the statement critically before forming your response. "
+                    "Reassess the statement carefully and critically before responding. "
-                    "If you disagree after careful reconsideration, explain why."
+                    "If, after reflection, you find reasons to disagree or qualify it, explain your reasoning. "
+                    "Likewise, if you find reasons to agree, articulate them clearly and justify your agreement."
                 ),
             }
 
@@ -165,11 +168,12 @@ class ChallengeTool(SimpleTool):
             The statement wrapped in challenge instructions
         """
         return (
-            f"CHALLENGE THIS STATEMENT - Do not automatically agree:\n\n"
+            f"CRITICAL REASSESSMENT – Do not automatically agree:\n\n"
             f'"{prompt}"\n\n'
-            f"Is this actually correct? Check carefully. If it's wrong, incomplete, misleading or incorrect, "
+            f"Carefully evaluate the statement above. Is it accurate, complete, and well-reasoned? "
-            f"you must say so. Provide your honest assessment, not automatic agreement. If you "
+            f"Investigate if needed before replying, and stay focused. If you identify flaws, gaps, or misleading "
-            f"feel there is merit in what the user is saying, explain WHY you agree."
+            f"points, explain them clearly. Likewise, if you find the reasoning sound, explain why it holds up. "
+            f"Respond with thoughtful analysis—stay to the point and avoid reflexive agreement."
         )
 
     # Required method implementations from SimpleTool