diff --git a/app/services/images/optimizer.rb b/app/services/images/optimizer.rb
index 0bffe1f53..b114ed8d5 100644
--- a/app/services/images/optimizer.rb
+++ b/app/services/images/optimizer.rb
@@ -38,11 +38,20 @@ module Images
     }.freeze
 
     def self.imgproxy(img_src, **kwargs)
-      options = DEFAULT_IMGPROXY_OPTIONS.merge(kwargs).reject { |_, v| v.blank? }
+      translated_options = translate_cloudinary_options(kwargs)
+      options = DEFAULT_IMGPROXY_OPTIONS.merge(translated_options).reject { |_, v| v.blank? }
       Imgproxy.config.endpoint ||= get_imgproxy_endpoint
       Imgproxy.url_for(img_src, options)
     end
 
+    def self.translate_cloudinary_options(options)
+      if options[:crop] == "fill"
+        options[:resizing_type] = "fill"
+      end
+
+      options
+    end
+
     def self.imgproxy_enabled?
       Imgproxy.config.key.present? && Imgproxy.config.salt.present?
     end
diff --git a/lib/data_update_scripts/20201026155851_resave_to_bust_cache_for_imgproxy.rb b/lib/data_update_scripts/20201026155851_resave_to_bust_cache_for_imgproxy.rb
new file mode 100644
index 000000000..15198d11f
--- /dev/null
+++ b/lib/data_update_scripts/20201026155851_resave_to_bust_cache_for_imgproxy.rb
@@ -0,0 +1,18 @@
+module DataUpdateScripts
+  class ResaveToBustCacheForImgproxy
+    def run
+      return unless ENV["FOREM_CONTEXT"] == "forem_cloud"
+
+      User.find_each do |user|
+        CacheBuster.bust_user(user)
+      end
+
+      Organization.find_each do |organization|
+        CacheBuster.bust_organization(organization, organization.slug)
+      end
+
+      Article.find_each(&:save)
+      Comment.find_each(&:save)
+    end
+  end
+end
diff --git a/spec/services/images/optimizer_spec.rb b/spec/services/images/optimizer_spec.rb
index bcf830438..5957b44cb 100644
--- a/spec/services/images/optimizer_spec.rb
+++ b/spec/services/images/optimizer_spec.rb
@@ -77,4 +77,11 @@ RSpec.describe Images::Optimizer, type: :service do
       expect(imgproxy_url).to match(%r{/s:500:500/aHR0cHM6Ly9pLmlt/Z3VyLmNvbS9mS1lL/Z280LnBuZw})
     end
   end
+
+  describe "#translate_cloudinary_options" do
+    it "Set resizing_type to fill if crop: fill is provided" do
+      options = { width: 100, height: 100, crop: "fill" }
+      expect(described_class.translate_cloudinary_options(options)).to include(resizing_type: "fill")
+    end
+  end
 end