diff --git a/app/logical/downloads/rewrite_strategies/tumblr.rb b/app/logical/downloads/rewrite_strategies/tumblr.rb
index 9771fc7be..11a462df0 100644
--- a/app/logical/downloads/rewrite_strategies/tumblr.rb
+++ b/app/logical/downloads/rewrite_strategies/tumblr.rb
@@ -1,45 +1,60 @@
 module Downloads
   module RewriteStrategies
+    DOMAIN = '(data|(\d+\.)?media)\.tumblr\.com'
+    MD5 = '(?<md5>[0-9a-f]{32})'
+    FILENAME = '(?<filename>(tumblr_(inline_)?)?[a-z0-9]+(_r[0-9]+)?)'
+    SIZES = '(250|400|500|500h|540|1280|raw)'
+    EXT = '(?<ext>\w+)'
+
     class Tumblr < Base
       def rewrite(url, headers, data = {})
-        if url =~ %r{^https?://.*tumblr\.com}
-          url, headers = rewrite_cdn(url, headers)
-          url, headers = rewrite_thumbnails(url, headers)
-        end
+        url = rewrite_cdn(url)
+        url = rewrite_samples(url, headers)
 
         return [url, headers, data]
       end
 
     protected
-      def rewrite_thumbnails(url, headers)
-        if url =~ %r{^https?://.+\.tumblr\.com/(?:\w+/)?(?:tumblr_)?(\w+_)(\d+)(\..+)$}
-          match = $1
-          given_size = $2
-          file_ext = $3
+      # Look for the biggest available version on data.tumblr.com. A bigger
+      # version may or may not exist.
+      #
+      # http://40.media.tumblr.com/d8c6d49785c0842ee31ff26c010b7445/tumblr_naypopLln51tkufhoo2_500h.png
+      # => http://data.tumblr.com/d8c6d49785c0842ee31ff26c010b7445/tumblr_naypopLln51tkufhoo2_raw.png
+      #
+      # https://40.media.tumblr.com/de018501416a465d898d24ad81d76358/tumblr_nfxt7voWDX1rsd4umo1_r23_1280.jpg
+      # => http://data.tumblr.com/de018501416a465d898d24ad81d76358/tumblr_nfxt7voWDX1rsd4umo1_r23_raw.jpg
+      #
+      # https://68.media.tumblr.com/ee02048f5578595badc95905e17154b4/tumblr_inline_ofbr4452601sk4jd9_250.gif
+      # => http://data.tumblr.com/ee02048f5578595badc95905e17154b4/tumblr_inline_ofbr4452601sk4jd9_500.gif
+      #
+      # https://25.media.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_500.png
+      # => http://data.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_1280.png
+      #
+      # http://data.tumblr.com/0DNBGJovY5j3smfeQs8nB53z_400.jpg
+      # => http://data.tumblr.com/0DNBGJovY5j3smfeQs8nB53z_500.jpg
+      #
+      # http://data.tumblr.com/tumblr_m24kbxqKAX1rszquso1_1280.jpg
+      # => http://data.tumblr.com/tumblr_m24kbxqKAX1rszquso1_1280.jpg
+      def rewrite_samples(url, headers)
+        if url =~ %r!\Ahttps?://#{DOMAIN}/(?<dir>#{MD5}/)?#{FILENAME}_#{SIZES}\.#{EXT}\z!i
+          sizes = ["raw", 1280, 540, 500, 400, 250]
+          candidates = sizes.map do |size|
+            "http://data.tumblr.com/#{$~[:dir]}#{$~[:filename]}_#{size}.#{$~[:ext]}"
+          end
 
-          big_1280_url = url.sub(match + given_size, match + "1280")
-          if file_ext == ".gif"
-            res = http_head_request(big_1280_url, headers)
-            # Sometimes the 1280 version of a gif is actually a static jpeg. We don't want that so we only use the 1280 version if it really is a gif.
-            if res.is_a?(Net::HTTPSuccess) && res["content-type"] == "image/gif"
-              return [big_1280_url, headers]
-            end
-          else
-            if http_exists?(big_1280_url, headers)
-              return [big_1280_url, headers]
-            end
+          url = candidates.find do |candidate|
+            http_exists?(candidate, headers)
           end
         end
 
-        return [url, headers]
+        url
       end
 
-      def rewrite_cdn(url, headers)
-        if url =~ %r{https?://gs1\.wac\.edgecastcdn\.net/8019B6/data\.tumblr\.com/}
-          url.sub!("gs1.wac.edgecastcdn.net/8019B6/", "")
-        end
-
-        return [url, headers]
+      # https://gs1.wac.edgecastcdn.net/8019B6/data.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_500.png
+      # => http://data.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_500.png
+      def rewrite_cdn(url)
+        url.sub!(%r!\Ahttps?://gs1\.wac\.edgecastcdn\.net/8019B6/data\.tumblr\.com!i, "http://data.tumblr.com")
+        url
       end
     end
   end
diff --git a/test/helpers/download_helper.rb b/test/helpers/download_helper.rb
new file mode 100644
index 000000000..5a8efd928
--- /dev/null
+++ b/test/helpers/download_helper.rb
@@ -0,0 +1,24 @@
+module DownloadTestHelper
+  def assert_downloaded(expected_filesize, source)
+    tempfile = Tempfile.new("danbooru-test")
+    download = Downloads::File.new(source, tempfile.path)
+
+    assert_nothing_raised(Downloads::File::Error) do
+      download.download!
+    end
+
+    assert_equal(expected_filesize, tempfile.size, "Tested source URL: #{source}")
+  end
+
+  def assert_rewritten(expected_source, test_source)
+    tempfile = Tempfile.new("danbooru-test")
+    download = Downloads::File.new(test_source, tempfile.path)
+
+    rewritten_source, headers, _ = download.before_download(test_source, {}, {})
+    assert_equal(expected_source, rewritten_source, "Tested source URL: #{test_source}")
+  end
+
+  def assert_not_rewritten(source)
+    assert_rewritten(source, source)
+  end
+end
diff --git a/test/test_helper.rb b/test/test_helper.rb
index 16d22d0eb..623090386 100644
--- a/test/test_helper.rb
+++ b/test/test_helper.rb
@@ -11,9 +11,9 @@ end
 require File.expand_path('../../config/environment', __FILE__)
 require 'rails/test_help'
 require 'cache'
-require 'helpers/post_archive_test_helper'
 
 Dir[File.expand_path(File.dirname(__FILE__) + "/factories/*.rb")].each {|file| require file}
+Dir[File.expand_path(File.dirname(__FILE__) + "/helpers/*.rb")].each {|file| require file}
 
 Shoulda::Matchers.configure do |config|
   config.integrate do |with|
@@ -23,6 +23,13 @@ end
 
 class ActiveSupport::TestCase
   include PostArchiveTestHelper
+  include ReportbooruHelper
+  include DownloadTestHelper
+
+  setup do
+    mock_popular_search_service!
+    mock_missed_search_service!
+  end
 
   teardown do
     Cache.clear
@@ -49,13 +56,3 @@ end
 
 Delayed::Worker.delay_jobs = false
 TestAfterCommit.enabled = false
-
-require "helpers/reportbooru_helper"
-class ActiveSupport::TestCase
-  include ReportbooruHelper
-
-  setup do
-    mock_popular_search_service!
-    mock_missed_search_service!
-  end
-end
diff --git a/test/unit/downloads/pixiv_test.rb b/test/unit/downloads/pixiv_test.rb
index ed2349975..17da0da7c 100644
--- a/test/unit/downloads/pixiv_test.rb
+++ b/test/unit/downloads/pixiv_test.rb
@@ -2,29 +2,6 @@ require 'test_helper'
 
 module Downloads
   class PixivTest < ActiveSupport::TestCase
-    def assert_downloaded(expected_filesize, source)
-      tempfile = Tempfile.new("danbooru-test")
-      download = Downloads::File.new(source, tempfile.path)
-
-      assert_nothing_raised(Downloads::File::Error) do
-        download.download!
-      end
-
-      assert_equal(expected_filesize, tempfile.size, "Tested source URL: #{source}")
-    end
-
-    def assert_rewritten(expected_source, test_source)
-      tempfile = Tempfile.new("danbooru-test")
-      download = Downloads::File.new(test_source, tempfile.path)
-
-      rewritten_source, headers, _ = download.before_download(test_source, {}, {})
-      assert_equal(expected_source, rewritten_source, "Tested source URL: #{test_source}")
-    end
-
-    def assert_not_rewritten(source)
-      assert_rewritten(source, source)
-    end
-
     context "An ugoira site for pixiv" do
       setup do
         @tempfile = Tempfile.new("danbooru-test")
diff --git a/test/unit/downloads/tumblr_test.rb b/test/unit/downloads/tumblr_test.rb
index acfb77fb3..760800285 100644
--- a/test/unit/downloads/tumblr_test.rb
+++ b/test/unit/downloads/tumblr_test.rb
@@ -3,32 +3,75 @@ require 'test_helper'
 module Downloads
   class TumblrTest < ActiveSupport::TestCase
     context "a download for a tumblr 500 sample" do
-      setup do
-        @source = "http://24.media.tumblr.com/fc328250915434e66e8e6a92773f79d0/tumblr_mf4nshfibc1s0oswoo1_500.jpg"
-        @tempfile = Tempfile.new("danbooru-test")
-        @download = Downloads::File.new(@source, @tempfile.path)
-        @download.download!
-      end
-
-      should "instead change the source to the 1280 version" do
-        assert_equal("http://24.media.tumblr.com/fc328250915434e66e8e6a92773f79d0/tumblr_mf4nshfibc1s0oswoo1_1280.jpg", @download.source)
-      end
-
-      should "instead download the 1280 version" do
-        assert_equal(196_617, ::File.size(@tempfile.path))
+      should "instead download the raw version" do
+        @source = "https://24.media.tumblr.com/fc328250915434e66e8e6a92773f79d0/tumblr_mf4nshfibc1s0oswoo1_500.jpg"
+        @rewrite = "http://data.tumblr.com/fc328250915434e66e8e6a92773f79d0/tumblr_mf4nshfibc1s0oswoo1_raw.jpg"
+        assert_rewritten(@rewrite, @source)
+        assert_downloaded(196_617, @source)
       end
     end
 
-    context "a download for a tumblr 500 image without a larger size" do
-      setup do
-        @source = "http://25.media.tumblr.com/tumblr_lxbzel2H5y1r9yjhso1_500.jpg"
-        @tempfile = Tempfile.new("danbooru-test")
-        @download = Downloads::File.new(@source, @tempfile.path)
-        @download.download!
+    context "a download for a *.media.tumblr.com/tumblr_$id_$size image without a larger size" do
+      should "download the same version" do
+        @source = "https://25.media.tumblr.com/tumblr_lxbzel2H5y1r9yjhso1_500.jpg"
+        @rewrite = "http://data.tumblr.com/tumblr_lxbzel2H5y1r9yjhso1_500.jpg"
+        assert_rewritten(@rewrite, @source)
+        assert_downloaded(90_122, @source)
       end
+    end
 
-      should "download the 500 version" do
-        assert_equal(90_122, ::File.size(@tempfile.path))
+    context "a download for a *.media.tumblr.com/tumblr_$id_$size image with a larger size" do
+      should "download the best available version" do
+        @source = "https://25.media.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_500.png"
+        @rewrite = "http://data.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_1280.png"
+        assert_rewritten(@rewrite, @source)
+        assert_downloaded(34_060, @source)
+      end
+    end
+
+    context "a download for a *.media.tumblr.com/$hash/tumblr_$id_rN_$size image" do
+      should "download the best available version" do
+        @source = "https://33.media.tumblr.com/4b7fecf9a5a8284fbaefb051a2369b55/tumblr_npozqfwc9h1rt6u7do1_r1_500.gif"
+        @rewrite = "http://data.tumblr.com/4b7fecf9a5a8284fbaefb051a2369b55/tumblr_npozqfwc9h1rt6u7do1_r1_raw.gif"
+        assert_rewritten(@rewrite, @source)
+        assert_downloaded(1_234_017, @source)
+      end
+    end
+
+    context "a download for a *.media.tumblr.com/$hash/tumblr_inline_$id_$size image" do
+      should "download the best available version" do
+        @source = "https://68.media.tumblr.com/ee02048f5578595badc95905e17154b4/tumblr_inline_ofbr4452601sk4jd9_250.gif"
+        @rewrite = "http://data.tumblr.com/ee02048f5578595badc95905e17154b4/tumblr_inline_ofbr4452601sk4jd9_500.gif"
+        assert_rewritten(@rewrite, @source)
+        assert_downloaded(110_348, @source)
+      end
+    end
+
+    context "a download for a data.tumblr.com/$id_$size image with a larger size" do
+      should "download the best available version" do
+        @source = "http://data.tumblr.com/0DNBGJovY5j3smfeQs8nB53z_400.jpg"
+        @rewrite = "http://data.tumblr.com/0DNBGJovY5j3smfeQs8nB53z_500.jpg"
+        assert_rewritten(@rewrite, @source)
+        assert_downloaded(153_885, @source)
+      end
+    end
+
+    context "a download for a data.tumblr.com/tumblr_$id_$size.jpg image" do
+      should "download the best available version" do
+        @source = "http://data.tumblr.com/tumblr_m24kbxqKAX1rszquso1_250.jpg"
+        @rewrite = "http://data.tumblr.com/tumblr_m24kbxqKAX1rszquso1_1280.jpg"
+        assert_rewritten(@rewrite, @source)
+        assert_downloaded(296_399, @source)
+      end
+    end
+
+    context "a download for a gs1.wac.edgecastcdn.net image" do
+      should "rewrite to the full tumblr version" do
+        @source = "https://gs1.wac.edgecastcdn.net/8019B6/data.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_500.png"
+        @rewrite = "http://data.tumblr.com/tumblr_m2dxb8aOJi1rop2v0o1_1280.png"
+
+        assert_downloaded(34_060, @source)
+        assert_rewritten(@rewrite, @source)
       end
     end
   end