diff --git a/tools/__init__.py b/tools/__init__.py
index 79005cb..ad50777 100644
--- a/tools/__init__.py
+++ b/tools/__init__.py
@@ -26,7 +26,7 @@ from .preview_image import handle as preview_image_handler
 TOOL_REGISTRY = [
     Tool(
         name="read_image",
-        description="Reads an image from the disk and returns it as a full size image content object.",
+        description="Reads an image from the disk and returns it as a full size image.",
         schema={
             "type": "object",
             "properties": {"path": {"type": "string", "description": "Path to the image file"}},
@@ -75,7 +75,7 @@ TOOL_REGISTRY = [
     ),
     Tool(
         name="preview_image",
-        description="Generates small thumbnails (~70 tokens) and detailed info for images. Can take file paths, or indices/ranges from a contact sheet.",
+        description="Generates small thumbnails and provides detailed info for images. Can take file paths, or indices/ranges from a contact sheet.",
         schema={
             "type": "object",
             "properties": {
diff --git a/tools/contact_sheet.py b/tools/contact_sheet.py
index f5fe885..c1dda96 100644
--- a/tools/contact_sheet.py
+++ b/tools/contact_sheet.py
@@ -4,7 +4,7 @@ import io
 import datetime
 from pathlib import Path
 from typing import Any, Dict, List
-from PIL import Image, ImageDraw, ImageFont
+from PIL import Image, ImageDraw, ImageFont, ImageOps
 from tools.utils import format_relative_time, ToolError, COMMON_FONTS, get_file_info_list, sort_file_list, get_paginated_list
 
 logger = logging.getLogger("MattCP")
@@ -83,6 +83,8 @@ async def handle(args: Dict[str, Any]):
         
         try:
             with Image.open(full_path) as img:
+                # Apply EXIF orientation to fix sideways images
+                img = ImageOps.exif_transpose(img)
                 img.thumbnail((thumb_size, thumb_size))
                 off_x = (thumb_size - img.width) // 2
                 off_y = (thumb_size - img.height) // 2
diff --git a/tools/preview_image.py b/tools/preview_image.py
index 64404e2..283ad0c 100644
--- a/tools/preview_image.py
+++ b/tools/preview_image.py
@@ -5,7 +5,7 @@ import io
 import datetime
 from pathlib import Path
 from typing import Any, Dict, List, Tuple
-from PIL import Image
+from PIL import Image, ImageOps
 from tools.utils import format_relative_time, ToolError, get_file_info_list, sort_file_list
 
 logger = logging.getLogger("MattCP")
@@ -115,6 +115,8 @@ async def handle(args: Dict[str, Any]):
         try:
             stats = file_path.stat()
             with Image.open(file_path) as img:
+                # Apply EXIF orientation to fix sideways images
+                img = ImageOps.exif_transpose(img)
                 orig_w, orig_h = img.size
                 target_w, target_h = calculate_patch_dimensions(orig_w, orig_h)