diff --git a/modules/chat.py b/modules/chat.py
index 42c0d46d5a..459f099cbd 100644
--- a/modules/chat.py
+++ b/modules/chat.py
@@ -7,10 +7,12 @@
 import re
 import shutil
 import time
+import mimetypes
 from datetime import datetime
 from functools import partial
 from pathlib import Path
 
+import filetype
 import gradio as gr
 import yaml
 from jinja2.ext import loopcontrols
@@ -25,7 +27,7 @@
     convert_to_markdown,
     make_thumbnail
 )
-from modules.image_utils import open_image_safely
+from modules.image_utils import is_mime_type_vision_supported, open_image_safely
 from modules.logging_colors import logger
 from modules.text_generation import (
     generate_reply,
@@ -239,7 +241,7 @@ def generate_chat_prompt(user_input, state, **kwargs):
                 image_refs = ""
 
                 for attachment in metadata[user_key]["attachments"]:
-                    if attachment.get("type") == "image":
+                    if is_mime_type_vision_supported(attachment.get("type")):
                         # Add image reference for multimodal models
                         image_refs += "<__media__>"
                     elif state.get('include_past_attachments', True):
@@ -280,7 +282,7 @@ def generate_chat_prompt(user_input, state, **kwargs):
                     image_refs = ""
 
                     for attachment in metadata[user_key]["attachments"]:
-                        if attachment.get("type") == "image":
+                        if is_mime_type_vision_supported(attachment.get("type")):
                             image_refs += "<__media__>"
                         else:
                             filename = attachment.get("name", "file")
@@ -590,51 +592,48 @@ def add_message_attachment(history, row_idx, file_path, is_user=True):
     # Get file info using pathlib
     path = Path(file_path)
     filename = path.name
-    file_extension = path.suffix.lower()
+
+    # Get MIME type from path
+    mime_type: str | None
+    mime_type, _ = mimetypes.guess_file_type(path)
+
+    # Get MIME type from file
+    if mime_type is None:
+        mime_type = filetype.guess_mime(path)
 
     try:
-        # Handle image files
-        if file_extension in ['.jpg', '.jpeg', '.png', '.webp', '.bmp', '.gif']:
+        if is_mime_type_vision_supported(mime_type):
+            # Handle image files
             # Convert image to base64
             with open(path, 'rb') as f:
                 image_data = base64.b64encode(f.read()).decode('utf-8')
 
-            # Determine MIME type from extension
-            mime_type_map = {
-                '.jpg': 'image/jpeg',
-                '.jpeg': 'image/jpeg',
-                '.png': 'image/png',
-                '.webp': 'image/webp',
-                '.bmp': 'image/bmp',
-                '.gif': 'image/gif'
-            }
-            mime_type = mime_type_map.get(file_extension, 'image/jpeg')
-
             # Format as data URL
             data_url = f"data:{mime_type};base64,{image_data}"
 
             # Generate unique image ID
-            image_id = len([att for att in history['metadata'][key]["attachments"] if att.get("type") == "image"]) + 1
+            image_id = len([att for att in history['metadata'][key]["attachments"] if is_mime_type_vision_supported(att.get("type"))]) + 1
 
             attachment = {
                 "name": filename,
-                "type": "image",
+                "type": mime_type,
                 "image_data": data_url,
                 "image_id": image_id,
             }
-        elif file_extension == '.pdf':
+        elif mime_type == 'application/pdf':
             # Process PDF file
             content = extract_pdf_text(path)
             attachment = {
                 "name": filename,
-                "type": "application/pdf",
+                "type": mime_type,
                 "content": content,
             }
-        elif file_extension == '.docx':
+        elif mime_type == 'application/vnd.openxmlformats-officedocument.wordprocessingml.document':
+            # Process .docx file
             content = extract_docx_text(path)
             attachment = {
                 "name": filename,
-                "type": "application/docx",
+                "type": mime_type,
                 "content": content,
             }
         else:
@@ -644,7 +643,7 @@ def add_message_attachment(history, row_idx, file_path, is_user=True):
 
             attachment = {
                 "name": filename,
-                "type": "text/plain",
+                "type": mime_type or "text/plain",
                 "content": content,
             }
 
@@ -858,7 +857,7 @@ def chatbot_wrapper(text, state, regenerate=False, _continue=False, loading_mess
             user_key = f"user_{i}"
             if user_key in output['metadata'] and "attachments" in output['metadata'][user_key]:
                 for attachment in output['metadata'][user_key]["attachments"]:
-                    if attachment.get("type") == "image":
+                    if is_mime_type_vision_supported(attachment.get("type")):
                         all_image_attachments.append(attachment)
 
     # Add all collected image attachments to state for the generation
diff --git a/modules/html_generator.py b/modules/html_generator.py
index 312b66ad07..8125147582 100644
--- a/modules/html_generator.py
+++ b/modules/html_generator.py
@@ -10,6 +10,7 @@
 from PIL import Image, ImageOps
 
 from modules import shared
+from modules.image_utils import is_mime_type_vision_supported
 from modules.sane_markdown_lists import SaneListExtension
 from modules.utils import get_available_chat_styles
 
@@ -462,12 +463,13 @@ def format_message_attachments(history, role, index):
         attachments_html = '<div class="message-attachments">'
         for attachment in attachments:
             name = html.escape(attachment["name"])
+            mime_type = attachment.get("type")
 
-            if attachment.get("type") == "image":
+            if is_mime_type_vision_supported(mime_type):
                 image_data = attachment.get("image_data", "")
                 attachments_html += (
                     f'<div class="attachment-box image-attachment">'
-                    f'<img src="{image_data}" alt="{name}" class="image-preview" />'
+                    f'<img src="{image_data}" alt="{name}" type="{mime_type}" class="image-preview" />'
                     f'<div class="attachment-name">{name}</div>'
                     f'</div>'
                 )
diff --git a/modules/image_utils.py b/modules/image_utils.py
index d2809fef36..5f90dc1119 100644
--- a/modules/image_utils.py
+++ b/modules/image_utils.py
@@ -97,7 +97,7 @@ def convert_image_attachments_to_pil(image_attachments: List[dict]) -> List[Imag
     """Convert webui image_attachments format to PIL Images."""
     pil_images = []
     for attachment in image_attachments:
-        if attachment.get('type') == 'image' and 'image_data' in attachment:
+        if is_mime_type_vision_supported(attachment.get('type')) and 'image_data' in attachment:
             try:
                 image = decode_base64_image(attachment['image_data'])
                 if image.mode != 'RGB':
@@ -116,3 +116,42 @@ def convert_openai_messages_to_images(messages: List[dict]) -> List[Image.Image]
             _, images = process_message_content(message['content'])
             all_images.extend(images)
     return all_images
+
+
+def is_mime_type_vision_supported(mime_type: str) -> bool:
+    return mime_type in {
+        'image/jpeg',
+        'image/png',
+        'image/webp',
+        'image/bmp',
+        'image/gif',
+        'image/tiff',
+        'image/avif',
+        # Uncommon pillow readable mime types
+        'image/x-dds',
+        'image/dds',
+        'image/x-eps',
+        'image/x-icns',
+        'image/x-icon',
+        'vnd.microsoft.icon',
+        'image/jp2',
+        'image/x-jp2-codestream',
+        'image/jpx',
+        'image/vnd.zbrush.pcx',
+        'image/x-portable-pixmap',
+        'image/qoi',
+        'image/x-qoi',
+        'image/x-sgi',
+        'image/x-tga',
+        'image/x-xbitmap',
+        'image/x-win-bitmap',
+        'image/fits',
+        'image/vnd.fpx',
+        'image/x-fpx',
+        'image/x-photo-cd',
+        'image/vnd.adobe.photoshop',
+        'image/x-sun-raster',
+        'image/emf',
+        'image/wmf',
+        'image/x-xpixmap',
+    }
diff --git a/requirements/full/requirements.txt b/requirements/full/requirements.txt
index dd74ed52e9..63b05e980f 100644
--- a/requirements/full/requirements.txt
+++ b/requirements/full/requirements.txt
@@ -6,6 +6,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 flash-linear-attention==0.4.*
 html2text==2025.4.15
 huggingface-hub==0.36.0
diff --git a/requirements/full/requirements_amd.txt b/requirements/full/requirements_amd.txt
index 3475c161ac..1375acfd0a 100644
--- a/requirements/full/requirements_amd.txt
+++ b/requirements/full/requirements_amd.txt
@@ -5,6 +5,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/full/requirements_amd_noavx2.txt b/requirements/full/requirements_amd_noavx2.txt
index 05077a32a6..67b4c5ce10 100644
--- a/requirements/full/requirements_amd_noavx2.txt
+++ b/requirements/full/requirements_amd_noavx2.txt
@@ -5,6 +5,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/full/requirements_apple_intel.txt b/requirements/full/requirements_apple_intel.txt
index f591fa251e..cf86336ad1 100644
--- a/requirements/full/requirements_apple_intel.txt
+++ b/requirements/full/requirements_apple_intel.txt
@@ -5,6 +5,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/full/requirements_apple_silicon.txt b/requirements/full/requirements_apple_silicon.txt
index 6ff4753d4b..85dda581c2 100644
--- a/requirements/full/requirements_apple_silicon.txt
+++ b/requirements/full/requirements_apple_silicon.txt
@@ -5,6 +5,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/full/requirements_cpu_only.txt b/requirements/full/requirements_cpu_only.txt
index bd0776daea..9375e4cf7d 100644
--- a/requirements/full/requirements_cpu_only.txt
+++ b/requirements/full/requirements_cpu_only.txt
@@ -5,6 +5,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/full/requirements_cpu_only_noavx2.txt b/requirements/full/requirements_cpu_only_noavx2.txt
index 39a06cdbe0..291ec8ca7d 100644
--- a/requirements/full/requirements_cpu_only_noavx2.txt
+++ b/requirements/full/requirements_cpu_only_noavx2.txt
@@ -5,6 +5,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/full/requirements_noavx2.txt b/requirements/full/requirements_noavx2.txt
index 3ff17704be..e664fabff0 100644
--- a/requirements/full/requirements_noavx2.txt
+++ b/requirements/full/requirements_noavx2.txt
@@ -6,6 +6,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 flash-linear-attention==0.4.*
 html2text==2025.4.15
 huggingface-hub==0.36.0
diff --git a/requirements/full/requirements_nowheels.txt b/requirements/full/requirements_nowheels.txt
index dc740dc86f..fe1fc16bdf 100644
--- a/requirements/full/requirements_nowheels.txt
+++ b/requirements/full/requirements_nowheels.txt
@@ -5,6 +5,7 @@ datasets
 diffusers==0.36.*
 einops
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements.txt b/requirements/portable/requirements.txt
index 2f6bf51142..f6b5d08c16 100644
--- a/requirements/portable/requirements.txt
+++ b/requirements/portable/requirements.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_amd.txt b/requirements/portable/requirements_amd.txt
index 209610ceb9..c657f61e57 100644
--- a/requirements/portable/requirements_amd.txt
+++ b/requirements/portable/requirements_amd.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_amd_noavx2.txt b/requirements/portable/requirements_amd_noavx2.txt
index 29a1f72b04..abf9ef73f0 100644
--- a/requirements/portable/requirements_amd_noavx2.txt
+++ b/requirements/portable/requirements_amd_noavx2.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_apple_intel.txt b/requirements/portable/requirements_apple_intel.txt
index 8812ac39f5..cf3c653710 100644
--- a/requirements/portable/requirements_apple_intel.txt
+++ b/requirements/portable/requirements_apple_intel.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_apple_silicon.txt b/requirements/portable/requirements_apple_silicon.txt
index c627cfd456..1d8d5a6936 100644
--- a/requirements/portable/requirements_apple_silicon.txt
+++ b/requirements/portable/requirements_apple_silicon.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_cpu_only.txt b/requirements/portable/requirements_cpu_only.txt
index 5ca660adfc..3f6859971b 100644
--- a/requirements/portable/requirements_cpu_only.txt
+++ b/requirements/portable/requirements_cpu_only.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_cpu_only_noavx2.txt b/requirements/portable/requirements_cpu_only_noavx2.txt
index 5bb282eb18..8c9848e2bd 100644
--- a/requirements/portable/requirements_cpu_only_noavx2.txt
+++ b/requirements/portable/requirements_cpu_only_noavx2.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_noavx2.txt b/requirements/portable/requirements_noavx2.txt
index ecce4a2f7d..b07e2c885e 100644
--- a/requirements/portable/requirements_noavx2.txt
+++ b/requirements/portable/requirements_noavx2.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_nowheels.txt b/requirements/portable/requirements_nowheels.txt
index c9831985e5..6a05bef68f 100644
--- a/requirements/portable/requirements_nowheels.txt
+++ b/requirements/portable/requirements_nowheels.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_vulkan.txt b/requirements/portable/requirements_vulkan.txt
index 4b3adddc3d..21c57e3c46 100644
--- a/requirements/portable/requirements_vulkan.txt
+++ b/requirements/portable/requirements_vulkan.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6
diff --git a/requirements/portable/requirements_vulkan_noavx2.txt b/requirements/portable/requirements_vulkan_noavx2.txt
index 8d6acdd78e..f800adbf16 100644
--- a/requirements/portable/requirements_vulkan_noavx2.txt
+++ b/requirements/portable/requirements_vulkan_noavx2.txt
@@ -1,5 +1,6 @@
 audioop-lts<1.0; python_version >= "3.13"
 fastapi==0.112.4
+filetype==1.2.0
 html2text==2025.4.15
 huggingface-hub==0.36.0
 jinja2==3.1.6