diff --git a/packages/core/integration-tests/test/image.js b/packages/core/integration-tests/test/image.js
index 4299e050aed..a12897068cf 100644
--- a/packages/core/integration-tests/test/image.js
+++ b/packages/core/integration-tests/test/image.js
@@ -113,6 +113,31 @@ describe('image', function() {
     assert(output.length < input.length);
   });
 
+  it('should lossless optimise progressive JPEGs', async function() {
+    let img = path.join(__dirname, '/integration/image/banana.jpg');
+    let b = await bundle(img, {
+      defaultTargetOptions: {
+        shouldOptimize: true,
+      },
+      logLevel: 'verbose',
+    });
+
+    const imagePath = b.getBundles().find(b => b.type === 'jpg').filePath;
+
+    // let input = await inputFS.readFile(img);
+    // let inputRaw = await sharp(input)
+    //   .toFormat('raw')
+    //   .toBuffer();
+    // Check validity of image
+    let output = await outputFS.readFile(imagePath);
+    await sharp(output)
+      .toFormat('raw')
+      .toBuffer();
+
+    // assert(outputRaw.equals(inputRaw));
+    // assert(output.length < input.length);
+  });
+
   it('should lossless optimise PNGs', async function() {
     let img = path.join(__dirname, '/integration/image/clock.png');
     let b = await bundle(img, {
diff --git a/packages/core/integration-tests/test/integration/image/banana.jpg b/packages/core/integration-tests/test/integration/image/banana.jpg
new file mode 100644
index 00000000000..23b5408399e
Binary files /dev/null and b/packages/core/integration-tests/test/integration/image/banana.jpg differ
diff --git a/packages/optimizers/image/package.json b/packages/optimizers/image/package.json
index 686b08ba34b..57bbf8ff2d8 100644
--- a/packages/optimizers/image/package.json
+++ b/packages/optimizers/image/package.json
@@ -34,6 +34,7 @@
   "dependencies": {
     "@parcel/plugin": "^2.0.0",
     "@parcel/utils": "^2.0.0",
+    "@parcel/diagnostic": "^2.0.0",
     "detect-libc": "^1.0.3"
   },
   "devDependencies": {
diff --git a/packages/optimizers/image/src/ImageOptimizer.js b/packages/optimizers/image/src/ImageOptimizer.js
index e12cb53d3fc..5f4f506ffdc 100644
--- a/packages/optimizers/image/src/ImageOptimizer.js
+++ b/packages/optimizers/image/src/ImageOptimizer.js
@@ -1,18 +1,36 @@
 // @flow
+import path from 'path';
+import process from 'process';
 import {Optimizer} from '@parcel/plugin';
 import {blobToBuffer} from '@parcel/utils';
+import {md} from '@parcel/diagnostic';
 import {optimize} from '../native';
 
 export default (new Optimizer({
-  async optimize({bundle, contents}) {
+  async optimize({bundle, contents, logger}) {
     if (!bundle.env.shouldOptimize) {
       return {contents};
     }
 
     let buffer = await blobToBuffer(contents);
-    let optimized = optimize(bundle.type, buffer);
-    return {
-      contents: optimized.length < buffer.length ? optimized : buffer,
-    };
+
+    // Attempt to optimize it, if the optimize fails we log a warning...
+    try {
+      let optimized = optimize(bundle.type, buffer);
+      return {
+        contents: optimized.length < buffer.length ? optimized : buffer,
+      };
+    } catch (err) {
+      const filepath = bundle.getMainEntry()?.filePath;
+      const filename = filepath
+        ? path.relative(process.cwd(), filepath)
+        : 'unknown';
+      logger.warn({
+        message: md`Could not optimize image ${filename}: ${err.message}`,
+        stack: err.stack,
+      });
+    }
+
+    return {contents: buffer};
   },
 }): Optimizer);