--- a/core/management/commands/ssl_images.py	Mon Feb 09 20:25:13 2015 -0600
+++ b/core/management/commands/ssl_images.py	Tue Feb 10 20:36:34 2015 -0600
@@ -171,10 +171,14 @@
     # Check to see if the image is available via https first.
     new_url = check_https_availability(parsed_url)
     if new_url:
+        url_cache[src] = new_url
         return new_url
 
     # If none of the above worked, try to download and upload to our S3 bucket
-    return save_image_to_cloud(src)
+    new_url = save_image_to_cloud(src)
+    if new_url:
+        url_cache[src] = new_url
+    return new_url
 
 
 def check_https_availability(parsed_url):
@@ -215,10 +219,7 @@
     fn = download_image(src)
     if fn:
         resize_image(fn)
-        new_url = upload_image(fn)
-        if new_url:
-            url_cache[src] = new_url
-        return new_url
+        return upload_image(fn)
     return None
 
 
@@ -355,7 +356,7 @@
             warn_if_image_refs(txt, model_name, model.pk)
             new_txt = process_post(txt)
             if txt != new_txt:
-                logger.info("Content changed on %s #%d (pk= %d)",
+                logger.info("Content changed on %s #%d (pk = %d)",
                             model_name, n + i, model.pk)
                 logger.debug("original: %s", txt)
                 logger.debug("changed:  %s", new_txt)

--- a/core/tests/test_ssl_images.py	Mon Feb 09 20:25:13 2015 -0600
+++ b/core/tests/test_ssl_images.py	Tue Feb 10 20:36:34 2015 -0600
@@ -1,16 +1,21 @@
 """Unit tests for the ssl_images management command."""
 import re
 import unittest
+from urlparse import urlparse
 
 import mock
 
 from core.management.commands.ssl_images import process_post
+import core.management.commands.ssl_images
 
 
 class ProcessPostTestCase(unittest.TestCase):
 
     SG101_RE = re.compile(r'http://(?:www\.)?surfguitar101.com/', re.I)
 
+    def tearDown(self):
+        core.management.commands.ssl_images.url_cache = {}
+
     def test_empty_string(self):
         s = process_post('')
         self.assertEqual(s, '')
@@ -117,6 +122,8 @@
         self.assertEqual(expected, result)
 
     @mock.patch('core.management.commands.ssl_images.save_image_to_cloud')
+    @mock.patch('core.management.commands.ssl_images.check_https_availability',
+                new=lambda r: None)
     def test_simple_replacement(self, upload_mock):
         old_src = 'http://example.com/images/my_image.jpg'
         new_src = 'https://cloud.com/ABCDEF.jpg'
@@ -133,6 +140,8 @@
         upload_mock.assert_called_once_with(old_src)
 
     @mock.patch('core.management.commands.ssl_images.save_image_to_cloud')
+    @mock.patch('core.management.commands.ssl_images.check_https_availability',
+                new=lambda r: None)
     def test_multiple_replacement(self, upload_mock):
         old_src = [
             'http://example.com/images/my_image.jpg',
@@ -163,6 +172,8 @@
         self.assertEqual(upload_mock.call_args_list, expected_args)
 
     @mock.patch('core.management.commands.ssl_images.save_image_to_cloud')
+    @mock.patch('core.management.commands.ssl_images.check_https_availability',
+                new=lambda r: None)
     def test_multiple_replacement_2(self, upload_mock):
         old_src = [
             'http://example.com/images/my_image.jpg',
@@ -192,3 +203,65 @@
         result = process_post(test_str)
         self.assertEqual(expected, result)
         upload_mock.assert_called_once_with(old_src[0])
+
+    @mock.patch('core.management.commands.ssl_images.save_image_to_cloud')
+    @mock.patch('core.management.commands.ssl_images.check_https_availability',
+                new=lambda r: None)
+    def test_caching(self, upload_mock):
+        old_src = [
+            'http://example.com/images/my_image.jpg',
+            'http://example.com/static/wow.gif',
+            'http://example.com/images/my_image.jpg',
+        ]
+        new_src = [
+            'https://cloud.com/some/path/012345.jpg',
+            'https://cloud.com/some/path/6789AB.gif',
+            'https://cloud.com/some/path/012345.jpg',
+        ]
+
+        template = """Here is a really cool http: based image:
+            ![flyer]({})
+            Cool, right?
+            Another one: ![pic]({})
+            And finally
+            ![an image]({})
+            """
+
+        test_str = template.format(*old_src)
+        expected = template.format(*new_src)
+
+        upload_mock.side_effect = new_src
+        result = process_post(test_str)
+        self.assertEqual(expected, result)
+        expected_args = [mock.call(c) for c in old_src[:2]]
+        self.assertEqual(upload_mock.call_args_list, expected_args)
+
+    @mock.patch('core.management.commands.ssl_images.check_https_availability')
+    def test_https_availability(self, check_https_mock):
+        old_src = [
+            'http://example.com/images/my_image.jpg',
+            'http://example.com/static/wow.gif',
+            'http://example.com/images/another_image.jpg',
+        ]
+        new_src = [
+            'https://example.com/images/my_image.jpg',
+            'https://example.com/static/wow.gif',
+            'https://example.com/images/another_image.jpg',
+        ]
+
+        template = """Here is a really cool http: based image:
+            ![flyer]({})
+            Cool, right?
+            Another one: ![pic]({})
+            And finally
+            ![an image]({})
+            """
+
+        test_str = template.format(*old_src)
+        expected = template.format(*new_src)
+
+        check_https_mock.side_effect = new_src
+        result = process_post(test_str)
+        self.assertEqual(expected, result)
+        expected_args = [mock.call(urlparse(c)) for c in old_src]
+        self.assertEqual(check_https_mock.call_args_list, expected_args)