diff --git a/app/assets/stylesheets/common/d-editor.scss b/app/assets/stylesheets/common/d-editor.scss
index c4a7979588b..401a4cc4f60 100644
--- a/app/assets/stylesheets/common/d-editor.scss
+++ b/app/assets/stylesheets/common/d-editor.scss
@@ -187,6 +187,10 @@
   &.site-icon {
     padding-bottom: 0;
   }
+  &.resizable {
+    object-fit: cover;
+    object-position: top;
+  }
 }
 
 .d-editor-preview .image-wrapper {
diff --git a/lib/cooked_post_processor.rb b/lib/cooked_post_processor.rb
index bd56c12ca04..2ec33c0d2c7 100644
--- a/lib/cooked_post_processor.rb
+++ b/lib/cooked_post_processor.rb
@@ -308,29 +308,34 @@ class CookedPostProcessor
   end
 
   def convert_to_link!(img)
+    w, h = img["width"].to_i, img["height"].to_i
+    user_width, user_height = (w > 0 && h > 0 && [w, h]) ||
+                              get_size_from_attributes(img) ||
+                              get_size_from_image_sizes(img["src"], @opts[:image_sizes])
+
+    limit_size!(img)
+
     src = img["src"]
     return if src.blank? || is_a_hyperlink?(img) || is_svg?(img)
 
-    width, height = img["width"].to_i, img["height"].to_i
-    # TODO: store original dimentions in db
     original_width, original_height = (get_size(src) || [0, 0]).map(&:to_i)
-
-    # can't reach the image...
     if original_width == 0 || original_height == 0
       Rails.logger.info "Can't reach '#{src}' to get its dimension."
       return
     end
 
-    return if original_width <= width && original_height <= height
     return if original_width <= SiteSetting.max_image_width && original_height <= SiteSetting.max_image_height
 
-    crop   = SiteSetting.min_ratio_to_crop > 0
-    crop &&= original_width.to_f / original_height.to_f < SiteSetting.min_ratio_to_crop
+    user_width, user_height = [original_width, original_height] if user_width.to_i <= 0 && user_height.to_i <= 0
+    width, height = user_width, user_height
+
+    crop = SiteSetting.min_ratio_to_crop > 0 && width.to_f / height.to_f < SiteSetting.min_ratio_to_crop
 
     if crop
-      width, height = ImageSizer.crop(original_width, original_height)
-      img["width"] = width
-      img["height"] = height
+      width, height = ImageSizer.crop(width, height)
+      img["width"], img["height"] = width, height
+    else
+      width, height = ImageSizer.resize(width, height)
     end
 
     # if the upload already exists and is attached to a different post,
@@ -700,10 +705,7 @@ class CookedPostProcessor
 
   def post_process_images
     extract_images.each do |img|
-      unless add_image_placeholder!(img)
-        limit_size!(img)
-        convert_to_link!(img)
-      end
+      convert_to_link!(img) unless add_image_placeholder!(img)
     end
   end
 
diff --git a/spec/components/cooked_post_processor_spec.rb b/spec/components/cooked_post_processor_spec.rb
index 799e3a3cd3a..d9866515626 100644
--- a/spec/components/cooked_post_processor_spec.rb
+++ b/spec/components/cooked_post_processor_spec.rb
@@ -416,12 +416,17 @@ describe CookedPostProcessor do
       end
 
       context "with unsized images" do
+        fab!(:upload) { Fabricate(:image_upload, width: 123, height: 456) }
+
+        fab!(:post) do
+          Fabricate(:post, raw: <<~HTML)
+          <img src="#{upload.url}">
+          HTML
+        end
 
-        fab!(:post) { Fabricate(:post_with_unsized_images) }
         let(:cpp) { CookedPostProcessor.new(post) }
 
         it "adds the width and height to images that don't have them" do
-          FastImage.expects(:size).returns([123, 456])
           cpp.post_process
           expect(cpp.html).to match(/width="123" height="456"/)
           expect(cpp).to be_dirty
@@ -430,6 +435,8 @@ describe CookedPostProcessor do
       end
 
       context "with large images" do
+        fab!(:upload) { Fabricate(:image_upload, width: 1750, height: 2000) }
+
         fab!(:post) do
           Fabricate(:post, raw: <<~HTML)
           <img src="#{upload.url}">
@@ -441,13 +448,9 @@ describe CookedPostProcessor do
         before do
           SiteSetting.max_image_height = 2000
           SiteSetting.create_thumbnails = true
-          FastImage.expects(:size).returns([1750, 2000])
         end
 
         it "generates overlay information" do
-          OptimizedImage.expects(:resize).returns(true)
-          FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
-
           cpp.post_process
 
           expect(cpp.html).to match_html <<~HTML
@@ -468,6 +471,8 @@ describe CookedPostProcessor do
           end
 
           it 'should not add lightbox' do
+            FastImage.expects(:size).returns([1750, 2000])
+
             cpp.post_process
 
             expect(cpp.html).to match_html <<~HTML
@@ -482,6 +487,8 @@ describe CookedPostProcessor do
           end
 
           it 'should not add lightbox' do
+            FastImage.expects(:size).returns([1750, 2000])
+
             cpp.post_process
 
             expect(cpp.html).to match_html <<~HTML
@@ -495,6 +502,8 @@ describe CookedPostProcessor do
             end
 
             it 'should not add lightbox' do
+              FastImage.expects(:size).returns([1750, 2000])
+
               SiteSetting.crawl_images = true
               cpp.post_process
 
@@ -537,8 +546,8 @@ describe CookedPostProcessor do
 
           context "when the upload is attached to the correct post" do
             before do
+              FastImage.expects(:size).returns([1750, 2000])
               OptimizedImage.expects(:resize).returns(true)
-              FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
               Discourse.store.class.any_instance.expects(:has_been_uploaded?).at_least_once.returns(true)
               upload.update(secure: true, access_control_post: post)
             end
@@ -568,6 +577,8 @@ describe CookedPostProcessor do
       end
 
       context "with tall images" do
+        fab!(:upload) { Fabricate(:image_upload, width: 860, height: 2000) }
+
         fab!(:post) do
           Fabricate(:post, raw: <<~HTML)
           <img src="#{upload.url}">
@@ -578,10 +589,6 @@ describe CookedPostProcessor do
 
         before do
           SiteSetting.create_thumbnails = true
-          FastImage.expects(:size).returns([860, 2000])
-          OptimizedImage.expects(:resize).never
-          OptimizedImage.expects(:crop).returns(true)
-          FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
         end
 
         it "crops the image" do
@@ -594,6 +601,8 @@ describe CookedPostProcessor do
       end
 
       context "with iPhone X screenshots" do
+        fab!(:upload) { Fabricate(:image_upload, width: 1125, height: 2436) }
+
         fab!(:post) do
           Fabricate(:post, raw: <<~HTML)
           <img src="#{upload.url}">
@@ -604,10 +613,6 @@ describe CookedPostProcessor do
 
         before do
           SiteSetting.create_thumbnails = true
-          FastImage.expects(:size).returns([1125, 2436])
-          OptimizedImage.expects(:resize).returns(true)
-          OptimizedImage.expects(:crop).never
-          FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
         end
 
         it "crops the image" do
@@ -625,6 +630,8 @@ describe CookedPostProcessor do
       end
 
       context "with large images when using subfolders" do
+        fab!(:upload) { Fabricate(:image_upload, width: 1750, height: 2000) }
+
         fab!(:post) do
           Fabricate(:post, raw: <<~HTML)
           <img src="/subfolder#{upload.url}">
@@ -635,13 +642,10 @@ describe CookedPostProcessor do
 
         before do
           set_subfolder "/subfolder"
+          stub_request(:get, "http://#{Discourse.current_hostname}/subfolder#{upload.url}").to_return(status: 200, body: File.new(Discourse.store.path_for(upload)))
 
           SiteSetting.max_image_height = 2000
           SiteSetting.create_thumbnails = true
-          FastImage.expects(:size).returns([1750, 2000])
-          OptimizedImage.expects(:resize).returns(true)
-
-          FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
         end
 
         it "generates overlay information" do
@@ -670,6 +674,8 @@ describe CookedPostProcessor do
       end
 
       context "with title and alt" do
+        fab!(:upload) { Fabricate(:image_upload, width: 1750, height: 2000) }
+
         fab!(:post) do
           Fabricate(:post, raw: <<~HTML)
           <img src="#{upload.url}" title="WAT" alt="RED">
@@ -681,9 +687,6 @@ describe CookedPostProcessor do
         before do
           SiteSetting.max_image_height = 2000
           SiteSetting.create_thumbnails = true
-          FastImage.expects(:size).returns([1750, 2000])
-          OptimizedImage.expects(:resize).returns(true)
-          FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
         end
 
         it "generates overlay information using image title and ignores alt" do
@@ -701,6 +704,8 @@ describe CookedPostProcessor do
       end
 
       context "with title only" do
+        fab!(:upload) { Fabricate(:image_upload, width: 1750, height: 2000) }
+
         fab!(:post) do
           Fabricate(:post, raw: <<~HTML)
           <img src="#{upload.url}" title="WAT">
@@ -712,9 +717,6 @@ describe CookedPostProcessor do
         before do
           SiteSetting.max_image_height = 2000
           SiteSetting.create_thumbnails = true
-          FastImage.expects(:size).returns([1750, 2000])
-          OptimizedImage.expects(:resize).returns(true)
-          FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
         end
 
         it "generates overlay information using image title" do
@@ -732,6 +734,8 @@ describe CookedPostProcessor do
       end
 
       context "with alt only" do
+        fab!(:upload) { Fabricate(:image_upload, width: 1750, height: 2000) }
+
         fab!(:post) do
           Fabricate(:post, raw: <<~HTML)
           <img src="#{upload.url}" alt="RED">
@@ -743,9 +747,6 @@ describe CookedPostProcessor do
         before do
           SiteSetting.max_image_height = 2000
           SiteSetting.create_thumbnails = true
-          FastImage.expects(:size).returns([1750, 2000])
-          OptimizedImage.expects(:resize).returns(true)
-          FileStore::BaseStore.any_instance.expects(:get_depth_for).returns(0)
         end
 
         it "generates overlay information using image alt" do
diff --git a/spec/fabricators/upload_fabricator.rb b/spec/fabricators/upload_fabricator.rb
index 01d05d9da55..72bcb6c7232 100644
--- a/spec/fabricators/upload_fabricator.rb
+++ b/spec/fabricators/upload_fabricator.rb
@@ -21,6 +21,20 @@ Fabricator(:upload) do
   extension "png"
 end
 
+Fabricator(:image_upload, from: :upload) do
+  after_create do |upload|
+    file = Tempfile.new(['fabricated', '.png'])
+    `convert -size #{upload.width}x#{upload.height} xc:white "#{file.path}"`
+
+    upload.url = Discourse.store.store_upload(file, upload)
+    upload.sha1 = Upload.generate_digest(file.path)
+
+    WebMock
+      .stub_request(:get, "http://#{Discourse.current_hostname}#{upload.url}")
+      .to_return(status: 200, body: File.new(file.path))
+  end
+end
+
 Fabricator(:video_upload, from: :upload) do
   original_filename "video.mp4"
   width nil