diff --git a/assets/sprites/portraits/ana_portrait.png b/assets/sprites/portraits/ana_portrait.png
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diff --git a/assets/sprites/portraits/arborist_portrait.png b/assets/sprites/portraits/arborist_portrait.png
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diff --git a/assets/sprites/portraits/gronk_portrait.png b/assets/sprites/portraits/gronk_portrait.png
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diff --git a/assets/sprites/portraits/ivan_portrait.png b/assets/sprites/portraits/ivan_portrait.png
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diff --git a/assets/sprites/portraits/kai_portrait.png b/assets/sprites/portraits/kai_portrait.png
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diff --git a/assets/sprites/portraits/kustos_portrait.png b/assets/sprites/portraits/kustos_portrait.png
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diff --git a/assets/sprites/portraits/pek_portrait.png b/assets/sprites/portraits/pek_portrait.png
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diff --git a/assets/sprites/portraits/tehnik_portrait.png b/assets/sprites/portraits/tehnik_portrait.png
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diff --git a/assets/sprites/portraits/zombi_skavt_portrait.png b/assets/sprites/portraits/zombi_skavt_portrait.png
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diff --git a/assets/sprites/portraits/zupan_portrait.png b/assets/sprites/portraits/zupan_portrait.png
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diff --git a/scripts/generate_dialogue_portraits.py b/scripts/generate_dialogue_portraits.py
new file mode 100644
index 000000000..182c5b634
--- /dev/null
+++ b/scripts/generate_dialogue_portraits.py
@@ -0,0 +1,63 @@
+#!/usr/bin/env python3
+"""
+Generate dialogue portraits (64x64px face crops) from master references
+"""
+from PIL import Image
+import os
+
+# Character reference mappings
+CHARACTERS = {
+    'kai_portrait.png': 'references/main_characters/kai/master_reference_nobg.png',
+    'ana_portrait.png': 'references/main_characters/ana/master_reference_nobg.png',
+    'gronk_portrait.png': 'references/main_characters/gronk/master_reference_nobg.png',
+    'ivan_portrait.png': 'references/npcs/ivan_kovac/master_reference_nobg.png',
+    'zombi_skavt_portrait.png': 'references/companions/zombie_scout/master_reference_nobg.png',
+    'pek_portrait.png': 'references/npcs/pek/master_reference.png',
+    'tehnik_portrait.png': 'references/npcs/tehnik/master_reference.png',
+    'kustos_portrait.png': 'references/npcs/kustos/master_reference.png',
+    'zupan_portrait.png': 'references/npcs/mayor/master_reference.png',
+    'arborist_portrait.png': 'references/npcs/arborist/master_reference.png',
+}
+
+def create_portrait(input_path, output_path, size=64):
+    """Crop top portion (head) from master reference and resize to portrait size"""
+    if not os.path.exists(input_path):
+        print(f"⚠️  SKIP: {input_path} not found")
+        return
+    
+    img = Image.open(input_path)
+    width, height = img.size
+    
+    # Crop top 40% (head area) - assuming chibi proportions
+    crop_height = int(height * 0.4)
+    head_crop = img.crop((0, 0, width, crop_height))
+    
+    # Resize to 64x64 maintaining aspect ratio
+    head_crop.thumbnail((size, size), Image.Resampling.LANCZOS)
+    
+    # Create new 64x64 image with transparency
+    portrait = Image.new('RGBA', (size, size), (0, 0, 0, 0))
+    
+    # Center the cropped head
+    offset = ((size - head_crop.width) // 2, (size - head_crop.height) // 2)
+    portrait.paste(head_crop, offset, head_crop if head_crop.mode == 'RGBA' else None)
+    
+    # Save
+    portrait.save(output_path, 'PNG')
+    print(f"✅ Created: {output_path}")
+
+def main():
+    os.makedirs('assets/sprites/portraits', exist_ok=True)
+    
+    print("🎭 GENERATING DIALOGUE PORTRAITS FROM MASTER REFERENCES...")
+    print("=" * 60)
+    
+    for portrait_name, reference_path in CHARACTERS.items():
+        output_path = f'assets/sprites/portraits/{portrait_name}'
+        create_portrait(reference_path, output_path)
+    
+    print("=" * 60)
+    print("✅ PORTRAIT GENERATION COMPLETE!")
+
+if __name__ == '__main__':
+    main()