diff --git a/package.json b/package.json
index 6ba29584..75fe13d7 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "impro",
-  "version": "0.18.148",
+  "version": "0.18.149",
   "type": "module",
   "scripts": {
     "start": "rm -rf \"${BUILD_DIR:-build}\" && NODE_ENV=development eleventy --serve",
diff --git a/src/js/components/image-cropper.js b/src/js/components/image-cropper.js
index f104bd21..4b6b5024 100644
--- a/src/js/components/image-cropper.js
+++ b/src/js/components/image-cropper.js
@@ -337,6 +337,8 @@ class ImageCropper extends Component {
     outputCanvas.width = outputWidth;
     outputCanvas.height = outputHeight;
     const outputCtx = outputCanvas.getContext("2d");
+    outputCtx.imageSmoothingEnabled = true;
+    outputCtx.imageSmoothingQuality = "high";
     outputCtx.fillStyle = "#ffffff";
     outputCtx.fillRect(0, 0, outputWidth, outputHeight);
     outputCtx.drawImage(
@@ -351,7 +353,7 @@ class ImageCropper extends Component {
       outputHeight,
     );
 
-    return outputCanvas.toDataURL("image/jpeg", 0.9);
+    return outputCanvas.toDataURL("image/png");
   }
 }
 
diff --git a/src/js/imageCompressor.js b/src/js/imageCompressor.js
index 0710b4f1..c4882033 100644
--- a/src/js/imageCompressor.js
+++ b/src/js/imageCompressor.js
@@ -27,15 +27,17 @@ export class ImageCompressor {
     return Math.round((base64.length * 3) / 4);
   }
 
-  drawImageToCanvas({ img, width, height, quality }) {
+  renderImageToCanvas({ img, width, height }) {
     const canvas = document.createElement("canvas");
     canvas.width = width;
     canvas.height = height;
     const ctx = canvas.getContext("2d");
+    ctx.imageSmoothingEnabled = true;
+    ctx.imageSmoothingQuality = "high";
     ctx.fillStyle = "#ffffff";
     ctx.fillRect(0, 0, width, height);
     ctx.drawImage(img, 0, 0, width, height);
-    return canvas.toDataURL("image/jpeg", quality);
+    return canvas;
   }
 
   dataUrlToBlob(dataUrl) {
@@ -62,6 +64,10 @@ export class ImageCompressor {
     let bestWidth = 0;
     let bestHeight = 0;
 
+    let resizedCanvas = null;
+    let resizedWidth = 0;
+    let resizedHeight = 0;
+
     while (maxQuality - minQuality > 1) {
       if (attempts >= 4) break;
 
@@ -82,12 +88,17 @@ export class ImageCompressor {
         maxHeight: maxDimension,
       });
 
-      const result = this.drawImageToCanvas({
-        img,
-        width,
-        height,
-        quality: quality / 100,
-      });
+      if (
+        !resizedCanvas ||
+        resizedWidth !== width ||
+        resizedHeight !== height
+      ) {
+        resizedCanvas = this.renderImageToCanvas({ img, width, height });
+        resizedWidth = width;
+        resizedHeight = height;
+      }
+
+      const result = resizedCanvas.toDataURL("image/jpeg", quality / 100);
 
       if (this.estimateDataUrlSize(result) <= MAX_IMAGE_SIZE) {
         bestDataUrl = result;
diff --git a/tests/unit/specs/components/image-cropper.test.js b/tests/unit/specs/components/image-cropper.test.js
index 72c14d36..8e592fb3 100644
--- a/tests/unit/specs/components/image-cropper.test.js
+++ b/tests/unit/specs/components/image-cropper.test.js
@@ -149,8 +149,8 @@ describe("image-cropper", () => {
       const result = element.cropImage();
       assert(result !== null, "cropImage should return a value");
       assert(
-        result.startsWith("data:image/jpeg"),
-        "cropImage should return a JPEG data URL",
+        result.startsWith("data:image/png"),
+        "cropImage should return a lossless PNG data URL",
       );
     });
 
diff --git a/tests/unit/specs/imageCompressor.test.js b/tests/unit/specs/imageCompressor.test.js
index 1f1477dc..05e8f200 100644
--- a/tests/unit/specs/imageCompressor.test.js
+++ b/tests/unit/specs/imageCompressor.test.js
@@ -22,6 +22,7 @@ describe("imageCompressor", () => {
   const originalCreateElement = document.createElement;
 
   function installImageStubs(toDataURL = () => "data:image/jpeg;base64,") {
+    const calls = { contexts: [], drawnSizes: [], encodeCount: 0 };
     globalThis.Image = class {
       /** @param {string} _ */
       set src(_) {
@@ -32,19 +33,31 @@ describe("imageCompressor", () => {
     };
     document.createElement = function (tag) {
       if (tag === "canvas") {
-        return {
+        const canvas = {
           width: 0,
           height: 0,
-          getContext: () => ({
-            fillStyle: "",
-            fillRect: () => {},
-            drawImage: () => {},
-          }),
-          toDataURL: () => toDataURL(),
+          getContext: () => {
+            const ctx = {
+              fillStyle: "",
+              imageSmoothingEnabled: false,
+              imageSmoothingQuality: "low",
+              fillRect: () => {},
+              drawImage: (img, x, y, width, height) =>
+                calls.drawnSizes.push({ width, height }),
+            };
+            calls.contexts.push(ctx);
+            return ctx;
+          },
+          toDataURL: () => {
+            calls.encodeCount++;
+            return toDataURL();
+          },
         };
+        return canvas;
       }
       return originalCreateElement.call(document, tag);
     };
+    return calls;
   }
 
   afterEach(() => {
@@ -204,5 +217,30 @@ describe("imageCompressor", () => {
       assert(result.width > 0 && result.width <= 4000);
       assert(result.height > 0 && result.height <= 4000);
     });
+
+    it("resamples with high-quality smoothing", async () => {
+      const small = `data:image/jpeg;base64,${"A".repeat(16)}`;
+      const calls = installImageStubs(() => small);
+
+      await compressImage("data:image/jpeg;base64,AAAA");
+      assert(calls.contexts.length > 0, "expected a canvas context");
+      for (const ctx of calls.contexts) {
+        assert.deepEqual(ctx.imageSmoothingEnabled, true);
+        assert.deepEqual(ctx.imageSmoothingQuality, "high");
+      }
+    });
+
+    it("resamples once per output size, not once per quality probe", async () => {
+      const small = `data:image/jpeg;base64,${"A".repeat(16)}`;
+      const calls = installImageStubs(() => small);
+
+      await compressImage("data:image/jpeg;base64,AAAA");
+      // Every probe fits, so dimensions never shrink: one resample, many encodes.
+      assert.deepEqual(calls.drawnSizes, [{ width: 4000, height: 4000 }]);
+      assert(
+        calls.encodeCount > 1,
+        `expected multiple quality probes, got ${calls.encodeCount}`,
+      );
+    });
   });
 });