diff --git a/converters/npc.cs b/converters/npc.cs
index abfe32f..55bc196 100644
--- a/converters/npc.cs
+++ b/converters/npc.cs
@@ -860,7 +860,7 @@ namespace finder2e_foundry_converter.Converters
                 // Validate against constraints if available
                 if (!string.IsNullOrWhiteSpace(constraints))
                 {
-                    var (isValid, normalizedResponse) = ValidateResponse(trimmed, constraints);
+                    var (isValid, normalizedResponse) = ValidateResponse(trimmed, constraints, promptKey);
                     if (isValid)
                     {
                         Console.WriteLine($"✓ Response is valid: '{normalizedResponse}'");
@@ -972,8 +972,19 @@ namespace finder2e_foundry_converter.Converters
         /// <summary>
         /// Validate a response against constraints and return normalized response
         /// </summary>
-        private (bool isValid, string normalizedResponse) ValidateResponse(string response, string constraints)
+        private (bool isValid, string normalizedResponse) ValidateResponse(string response, string constraints, string promptKey = "")
         {
+            // Strip punctuation characters for validation (except for name and description prompts)
+            var isNameOrDescriptionPrompt = promptKey.Contains("name") || promptKey.Contains("description");
+            var cleanedResponse = response;
+            
+            if (!isNameOrDescriptionPrompt)
+            {
+                // Strip: _ , ; - ' . ! ? "
+                var charsToStrip = "_,;-'.!?\"";
+                cleanedResponse = new string(response.Where(c => !charsToStrip.Contains(c)).ToArray()).Trim();
+            }
+
             var allowed = constraints.Trim();
             var optionsStart = allowed.IndexOf(":");
 
@@ -996,13 +1007,13 @@ namespace finder2e_foundry_converter.Converters
             if (options.Count > 0)
             {
                 // Check exact match
-                if (options.Any(o => string.Equals(o, response, StringComparison.OrdinalIgnoreCase)))
+                if (options.Any(o => string.Equals(o, cleanedResponse, StringComparison.OrdinalIgnoreCase)))
                 {
-                    return (true, response);
+                    return (true, cleanedResponse);
                 }
 
                 // Try first word match
-                var firstWord = response.Split(new[] { ' ', '\t', '\r', '\n' }, StringSplitOptions.RemoveEmptyEntries).FirstOrDefault() ?? string.Empty;
+                var firstWord = cleanedResponse.Split(new[] { ' ', '\t', '\r', '\n' }, StringSplitOptions.RemoveEmptyEntries).FirstOrDefault() ?? string.Empty;
                 if (options.Any(o => string.Equals(o, firstWord, StringComparison.OrdinalIgnoreCase)))
                 {
                     return (true, firstWord);
@@ -1012,7 +1023,7 @@ namespace finder2e_foundry_converter.Converters
             }
 
             // No options parsed, accept any non-empty response
-            return (!string.IsNullOrWhiteSpace(response), response);
+            return (!string.IsNullOrWhiteSpace(cleanedResponse), cleanedResponse);
         }
     }
 }
diff --git a/llmflow/npc.toml b/llmflow/npc.toml
index 721b160..e8b6fda 100644
--- a/llmflow/npc.toml
+++ b/llmflow/npc.toml
@@ -20,57 +20,57 @@ question = "Based on the character level {level}, what is a fitting name for thi
 constraints = "Respond with only the name."
 
 [ability_score_modifier]
-question = "Based on the description, how would you rate the {modifierTier} ability score modifier for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the ability score modifier for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, Moderate, or Low."
 
 [perception_modifier]
-question = "Based on the description, how would you rate the {modifierTier} perception modifier for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the perception modifier for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, Moderate, Low, or Terrible."
 
 [skill_modifier]
-question = "Based on the description, how would you rate the {modifierTier} skill modifier for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the skill modifier for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, Moderate, or Low."
 
 [ac]
-question = "Based on the description, how would you rate the {modifierTier} armor class (AC) for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the armor class (AC) for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, Moderate, or Low."
 
 [saving_throw]
-question = "Based on the description, how would you rate the {modifierTier} saving throw for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the saving throw for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, Moderate, Low, or Terrible."
 
 [hp]
-question = "Based on the description, how would you rate the {modifierTier} hit points (HP) for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the hit points (HP) for a level {level} character in {system}?"
 constraints = "Respond with only a single word: High, Moderate, or Low."
 
 [resistance_or_weakness]
-question = "Based on the description, does this character have any notable resistances or weaknesses in {system}?"
+question = "Based on the description: {description}. Does this character have any notable resistances or weaknesses in {system}?"
 constraints = "Respond with only a single word: Yes or No."
 
 [strike_attack_bonus]
-question = "Based on the description, how would you rate the {modifierTier} strike attack bonus for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the strike attack bonus for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, Moderate, or Low."
 
 [strike_damage_roll]
-question = "Based on the description, what is the strike damage dice roll for a level {level} character in {system}?"
+question = "Based on the description: {description}. What is the strike damage dice roll for a level {level} character in {system}?"
 constraints = "Respond with only the dice notation (e.g., 1d8+3, 2d6)."
 
 [strike_damage_average]
-question = "Based on the description, what is the average strike damage for a level {level} character in {system}?"
+question = "Based on the description: {description}. What is the average strike damage for a level {level} character in {system}?"
 constraints = "Respond with only the numerical value of the average damage."
 
 [area_damage_roll]
-question = "Based on the description, what is the area damage dice roll for a level {level} character in {system} (unlimited: {unlimited})?"
+question = "Based on the description: {description}. What is the area damage dice roll for a level {level} character in {system} (unlimited: {unlimited})?"
 constraints = "Respond with only the dice notation (e.g., 2d6, 1d10)."
 
 [area_damage_average]
-question = "Based on the description, what is the average area damage for a level {level} character in {system} (unlimited: {unlimited})?"
+question = "Based on the description: {description}. What is the average area damage for a level {level} character in {system} (unlimited: {unlimited})?"
 constraints = "Respond with only the numerical value of the average damage."
 
 [spell_dc]
-question = "Based on the description, how would you rate the {modifierTier} spell DC for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the spell DC for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, or Moderate."
 
 [spell_attack_bonus]
-question = "Based on the description, how would you rate the {modifierTier} spell attack bonus for a level {level} character in {system}?"
+question = "Based on the description: {description}. How would you rate the spell attack bonus for a level {level} character in {system}?"
 constraints = "Respond with only a single word: Extreme, High, or Moderate."