diff --git a/requirements.txt b/requirements.txt
index a058d7411..fafd568c5 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -18,3 +18,4 @@ twilio==6.10.0
 cherrys==0.4
 redis==2.10.6
 ics==0.4
+pillow==5.2.0
diff --git a/uber/configspec.ini b/uber/configspec.ini
index b201b34b5..389e6d9a7 100644
--- a/uber/configspec.ini
+++ b/uber/configspec.ini
@@ -492,6 +492,11 @@ mits_email = string(default="MAGFest Indie Tabletop Showcase <tabletop@magfest.o
 # Goes at the bottom of all MITS automated emails.
 mits_email_signature = string(default=" - Janus, MITS Department Head")
 
+# We use these (width, height) measurements to mark uploaded images as
+# either a header or thumbnail. The measurements below are for Guidebook.
+mits_header_size = string_list(default=list('640','240'))
+mits_thumbnail_size = string_list(default=list('240','240'))
+
 
 # =============================
 # panels
diff --git a/uber/models/mits.py b/uber/models/mits.py
index 6d9c88528..69858d045 100644
--- a/uber/models/mits.py
+++ b/uber/models/mits.py
@@ -1,6 +1,7 @@
 import os
 from functools import wraps
 
+from PIL import Image
 from residue import CoerceUTF8 as UnicodeText, UTCDateTime, UUID
 from sideboard.lib import on_startup
 from sqlalchemy.schema import ForeignKey
@@ -161,6 +162,14 @@ def url(self):
     def filepath(self):
         return os.path.join(c.MITS_PICTURE_DIR, str(self.id))
 
+    @property
+    def is_header(self):
+        return Image.open(self.filepath).size == tuple(map(int, c.MITS_HEADER_SIZE))
+
+    @property
+    def is_thumbnail(self):
+        return Image.open(self.filepath).size == tuple(map(int, c.MITS_THUMBNAIL_SIZE))
+
 
 class MITSDocument(MagModel):
     team_id = Column(UUID, ForeignKey('mits_team.id'))
diff --git a/uber/templates/mits_applications/index.html b/uber/templates/mits_applications/index.html
index 699415858..18f85e6c7 100644
--- a/uber/templates/mits_applications/index.html
+++ b/uber/templates/mits_applications/index.html
@@ -103,6 +103,10 @@ <h3>Manage Your Pictures</h3>
                     <input type="submit" value="Delete" />
                 </form>
             </td>
+            <td>
+              {% if picture.is_header %}<em>Header</em>{% endif %}
+              {% if picture.is_thumbnail %}<em>Thumbnail</em>{% endif %}
+            </td>
         </tr>
     {% endfor %}
     </table>