diff --git a/telegram/inputfile.py b/telegram/inputfile.py
index 17cf18eb3..7fee1d882 100644
--- a/telegram/inputfile.py
+++ b/telegram/inputfile.py
@@ -26,8 +26,8 @@ except ImportError:
     from urllib2 import urlopen
 import mimetypes
 import os
-import re
 import sys
+import imghdr
 
 from .error import TelegramError
 
@@ -128,20 +128,9 @@ class InputFile(object):
         Returns:
           The str mimetype of an image.
         """
-        try:
-            header = stream[:10]
-
-            if re.match(b'GIF8', header):
-                return 'image/gif'
-
-            if re.match(b'\x89PNG', header):
-                return 'image/png'
-
-            if re.match(b'\xff\xd8\xff\xe0\x00\x10JFIF', header) or \
-               re.match(b'\xff\xd8\xff\xe1(.*){2}Exif', header):
-                return 'image/jpeg'
-        except IndexError as e:
-            raise TelegramError(str(e))
+        image = imghdr.what(None, stream)
+        if image:
+            return 'image/%s' % image
 
         raise TelegramError({'message': 'Could not parse file content'})
 
diff --git a/tests/test_bot.py b/tests/test_bot.py
index b6195e2d2..ef22cb14f 100644
--- a/tests/test_bot.py
+++ b/tests/test_bot.py
@@ -79,13 +79,27 @@ class BotTest(unittest.TestCase):
                                       chat_id=12173560)
         self.assertEqual('AgADAQADr6cxGzU8LQe6q0dMJD2rHYkP2ykABFymiQqJgjxRGGMAAgI', message.photo[0].file_id)
 
-    def testSendURLPhoto(self):
+    def testSendJPGURLPhoto(self):
         '''Test the telegram.Bot sendPhoto method'''
-        print('Testing sendPhoto - URL')
+        print('Testing testSendJPGURLPhoto - URL')
         message = self._bot.sendPhoto(photo=str('http://dummyimage.com/600x400/000/fff.jpg&text=telegram'),
                                       chat_id=12173560)
         self.assertEqual(822, message.photo[0].file_size)
 
+    def testSendPNGURLPhoto(self):
+        '''Test the telegram.Bot sendPhoto method'''
+        print('Testing testSendPNGURLPhoto - URL')
+        message = self._bot.sendPhoto(photo=str('http://dummyimage.com/600x400/000/fff.png&text=telegram'),
+                                      chat_id=12173560)
+        self.assertEqual(684, message.photo[0].file_size)
+
+    def testSendGIFURLPhoto(self):
+        '''Test the telegram.Bot sendPhoto method'''
+        print('Testing testSendGIFURLPhoto - URL')
+        message = self._bot.sendPhoto(photo=str('http://dummyimage.com/600x400/000/fff.gif&text=telegram'),
+                                      chat_id=12173560)
+        self.assertEqual(684, message.photo[0].file_size)
+
     def testSendAudio(self):
         '''Test the telegram.Bot sendAudio method'''
         print('Testing sendAudio - File')
@@ -107,6 +121,13 @@ class BotTest(unittest.TestCase):
                                          chat_id=12173560)
         self.assertEqual(12948, message.document.file_size)
 
+    def testSendGIFURLDocument(self):
+        '''Test the telegram.Bot sendDocument method'''
+        print('Testing sendDocument - File')
+        message = self._bot.sendPhoto(photo=str('http://dummyimage.com/600x400/000/fff.gif&text=telegram'),
+                                      chat_id=12173560)
+        self.assertEqual(684, message.photo[0].file_size)
+
     def testResendDocument(self):
         '''Test the telegram.Bot sendDocument method'''
         print('Testing sendDocument - Resend')