diff --git a/app/services/images/optimizer.rb b/app/services/images/optimizer.rb
index caeaff225020..92f9becb350e 100644
--- a/app/services/images/optimizer.rb
+++ b/app/services/images/optimizer.rb
@@ -5,7 +5,7 @@ def self.call(img_src, **kwargs)
 
       if imgproxy_enabled?
         imgproxy(img_src, **kwargs)
-      elsif cloudinary_enabled?
+      elsif cloudinary_enabled? && !cloudflare_contextually_preferred?(img_src)
         cloudinary(img_src, **kwargs)
       elsif cloudflare_enabled?
         cloudflare(img_src, **kwargs)
@@ -129,5 +129,13 @@ def self.extract_suffix_url(full_url)
       match = uri.path.match(%r{https?.+})
       CGI.unescape(match[0]) if match
     end
+
+    # This is a feature-flagged Cloudflare preference for hosted images only — works specifically with S3-hosted image sources.
+    def self.cloudflare_contextually_preferred?(img_src)
+      return false unless cloudflare_enabled?
+      return false unless FeatureFlag.enabled?(:cloudflare_preferred_for_hosted_images)
+
+      img_src&.start_with?("https://#{ApplicationConfig['AWS_BUCKET_NAME']}.s3.amazonaws.com")
+    end
   end
 end
diff --git a/spec/services/images/optimizer_spec.rb b/spec/services/images/optimizer_spec.rb
index 6b043917af1c..b25d031d5735 100644
--- a/spec/services/images/optimizer_spec.rb
+++ b/spec/services/images/optimizer_spec.rb
@@ -47,9 +47,25 @@
       expect(described_class).not_to have_received(:cloudinary)
       expect(described_class).to have_received(:imgproxy)
     end
+
+    context "when cloudflare is contextually preferred" do
+      before do
+        allow(described_class).to receive(:cloudflare_contextually_preferred?).and_return(true)
+        allow(described_class).to receive(:cloudflare_enabled?).and_return(true)
+        allow(described_class).to receive(:cloudflare)
+      end
+
+      it "prefers cloudflare over other services" do
+        described_class.call(image_url)
+        expect(described_class).to have_received(:cloudflare)
+        expect(described_class).not_to have_received(:cloudinary)
+        expect(described_class).not_to have_received(:imgproxy)
+      end
+    end
   end
 
   describe "#cloudinary", :cloudinary do
+
     it "performs exactly like cl_image_path" do
       cloudinary_url = cl_image_path(image_url,
                                      type: "fetch",
@@ -118,6 +134,7 @@
     end
 
     it "generates correct crop when CROP_WITH_IMAGGA_SCALE is set" do
+      allow(ApplicationConfig).to receive(:[]).with("CLOUDFLARE_IMAGES_DOMAIN").and_return(nil)
       allow(ApplicationConfig).to receive(:[]).with("CROP_WITH_IMAGGA_SCALE").and_return("true")
       cloudinary_url = cl_image_path(image_url,
                                      type: "fetch",
@@ -130,6 +147,7 @@
     end
 
     it "generates correct crop when CROP_WITH_IMAGGA_SCALE is set but never_imagga: true is passed" do
+      allow(ApplicationConfig).to receive(:[]).with("CLOUDFLARE_IMAGES_DOMAIN").and_return(nil)
       allow(ApplicationConfig).to receive(:[]).with("CROP_WITH_IMAGGA_SCALE").and_return("true")
       cl_url = cl_image_path(image_url,
                              type: "fetch",
@@ -312,4 +330,52 @@
       expect(described_class.translate_cloudinary_options(options)).to include(resizing_type: "fit")
     end
   end
+
+  describe "#cloudflare_contextually_preferred?" do
+    let(:aws_bucket_name) { "mybucket" }
+    let(:hosted_image_url) { "https://#{aws_bucket_name}.s3.amazonaws.com/path/to/image.jpg" }
+    let(:non_hosted_image_url) { "https://example.com/path/to/image.jpg" }
+  
+    before do
+      allow(ApplicationConfig).to receive(:[]).with("AWS_BUCKET_NAME").and_return(aws_bucket_name)
+    end
+  
+    context "when cloudflare is enabled and feature flag is on" do
+      before do
+        allow(described_class).to receive(:cloudflare_enabled?).and_return(true)
+        allow(FeatureFlag).to receive(:enabled?).with(:cloudflare_preferred_for_hosted_images).and_return(true)
+      end
+  
+      it "returns true for hosted images" do
+        expect(described_class.cloudflare_contextually_preferred?(hosted_image_url)).to be(true)
+      end
+  
+      it "returns false for non-hosted images" do
+        expect(described_class.cloudflare_contextually_preferred?(non_hosted_image_url)).to be(false)
+      end
+    end
+
+    context "when cloudflare is disabled" do
+      before do
+        allow(described_class).to receive(:cloudflare_enabled?).and_return(false)
+      end
+  
+      it "returns false regardless of image source" do
+        expect(described_class.cloudflare_contextually_preferred?(hosted_image_url)).to be(false)
+        expect(described_class.cloudflare_contextually_preferred?(non_hosted_image_url)).to be(false)
+      end
+    end
+
+    context "when feature flag is off" do
+      before do
+        allow(described_class).to receive(:cloudflare_enabled?).and_return(true)
+        allow(FeatureFlag).to receive(:enabled?).with(:cloudflare_preferred_for_hosted_images).and_return(false)
+      end
+
+      it "returns false regardless of image source" do
+        expect(described_class.cloudflare_contextually_preferred?(hosted_image_url)).to be(false)
+        expect(described_class.cloudflare_contextually_preferred?(non_hosted_image_url)).to be(false)
+      end
+    end
+  end
 end