diff --git a/app/logical/downloads/strategies/tumblr.rb b/app/logical/downloads/strategies/tumblr.rb
index 55d53601f..846ab516b 100644
--- a/app/logical/downloads/strategies/tumblr.rb
+++ b/app/logical/downloads/strategies/tumblr.rb
@@ -11,12 +11,22 @@ module Downloads
 
     protected
       def rewrite_thumbnails(url, headers)
-        if url =~ %r{^http?://.+\.tumblr\.com/(?:\w+/)?(?:tumblr_)?(\w+_)(250|400|500)\..+$}
+        if url =~ %r{^http?://.+\.tumblr\.com/(?:\w+/)?(?:tumblr_)?(\w+_)(250|400|500|1280)\..+$}
           match = $1
-          size = $2
-          big_url = url.sub(match + size, match + "1280")
-          if http_exists?(big_url, headers)
-            url = big_url
+          given_size = $2
+
+          big_500h_url = url.sub(match + given_size, match + "500h")
+          if http_exists?(big_500h_url, headers)
+            return [big_500h_url, headers]
+          end
+
+          if given_size == "1280"
+            return [url, headers]
+          end
+
+          big_1280_url = url.sub(match + given_size, match + "1280")
+          if http_exists?(big_1280_url, headers)
+            return [big_1280_url, headers]
           end
         end
 
diff --git a/test/fixtures/vcr_cassettes/download-tumblr-sample.yml b/test/fixtures/vcr_cassettes/download-tumblr-sample.yml
index d7e51ffad..87351dae6 100644
--- a/test/fixtures/vcr_cassettes/download-tumblr-sample.yml
+++ b/test/fixtures/vcr_cassettes/download-tumblr-sample.yml
@@ -7779,4 +7779,72 @@ http_interactions:
         pHpW+uDiy5JKkqKgFQCoBUAqA//Z
     http_version: 
   recorded_at: Thu, 28 Nov 2013 18:03:23 GMT
+- request:
+    method: head
+    uri: http://25.media.tumblr.com/tumblr_lxbzel2H5y1r9yjhso1_500h.jpg
+    body:
+      encoding: US-ASCII
+      string: ''
+    headers:
+      User-Agent:
+      - lowerbooru/2.36.0
+      Accept:
+      - ! '*/*'
+  response:
+    status:
+      code: 403
+      message: Forbidden
+    headers:
+      X-Amz-Request-Id:
+      - 71B57CCD3C6DDA59
+      X-Amz-Id-2:
+      - 4Sf4rVMjOtgOohpJ2G1XkXdjaVQ49LNEBI1DeIAyN+6TdzAEFi4Bf7ASYzgmW+Ly
+      Content-Type:
+      - application/xml
+      Server:
+      - AmazonS3
+      Content-Length:
+      - '1'
+      Date:
+      - Fri, 29 Nov 2013 21:06:02 GMT
+      Connection:
+      - keep-alive
+    body:
+      encoding: US-ASCII
+      string: ''
+    http_version: 
+  recorded_at: Fri, 29 Nov 2013 21:06:05 GMT
+- request:
+    method: head
+    uri: http://24.media.tumblr.com/fc328250915434e66e8e6a92773f79d0/tumblr_mf4nshfibc1s0oswoo1_500h.jpg
+    body:
+      encoding: US-ASCII
+      string: ''
+    headers:
+      User-Agent:
+      - lowerbooru/2.36.0
+      Accept:
+      - ! '*/*'
+  response:
+    status:
+      code: 403
+      message: Forbidden
+    headers:
+      Content-Type:
+      - application/xml
+      Date:
+      - Fri, 29 Nov 2013 21:06:03 GMT
+      Server:
+      - AmazonS3
+      X-Amz-Id-2:
+      - 3St4wTEbbc78MnStNWxXUEtPjmi9/Kuxk+1nANXxGWlwLr2qEAJiI/TL/gTpsx6v
+      X-Amz-Request-Id:
+      - 2A8C48C6C6C63E02
+      Connection:
+      - close
+    body:
+      encoding: US-ASCII
+      string: ''
+    http_version: 
+  recorded_at: Fri, 29 Nov 2013 21:06:06 GMT
 recorded_with: VCR 2.5.0