diff --git a/apps/web/src/components/tools/crop-settings.tsx b/apps/web/src/components/tools/crop-settings.tsx
index 8f787e71..9da3d3b8 100644
--- a/apps/web/src/components/tools/crop-settings.tsx
+++ b/apps/web/src/components/tools/crop-settings.tsx
@@ -5,6 +5,15 @@ import { ProgressCard } from "@/components/common/progress-card";
 import { useToolProcessor } from "@/hooks/use-tool-processor";
 import { useFileStore } from "@/stores/file-store";
 
+const EXTEND_PRESETS = [
+  { label: "16:9", aspect: 16 / 9 },
+  { label: "1:1", aspect: 1 },
+  { label: "4:3", aspect: 4 / 3 },
+  { label: "3:2", aspect: 3 / 2 },
+  { label: "9:16", aspect: 9 / 16 },
+  { label: "4:5", aspect: 4 / 5 },
+];
+
 const ASPECT_PRESETS = [
   { label: "Free", value: undefined as number | undefined },
   { label: "1:1", value: 1 },
@@ -26,6 +35,7 @@ export interface CropSettingsProps {
   onCropChange: (crop: Crop) => void;
   onAspectChange: (aspect: number | undefined) => void;
   onGridToggle: (show: boolean) => void;
+  onModeChange?: (mode: "standard" | "content-aware") => void;
 }
 
 export function CropSettings({
@@ -33,10 +43,14 @@ export function CropSettings({
   onCropChange,
   onAspectChange,
   onGridToggle,
+  onModeChange,
 }: CropSettingsProps) {
   const { files } = useFileStore();
-  const { processFiles, processAllFiles, processing, error, downloadUrl, progress } =
-    useToolProcessor("crop");
+  const standardCrop = useToolProcessor("crop");
+  const contentAwareCrop = useToolProcessor("content-aware-crop");
+  const [mode, setMode] = useState<"standard" | "content-aware">("standard");
+  const active = mode === "content-aware" ? contentAwareCrop : standardCrop;
+  const { processFiles, processAllFiles, processing, error, downloadUrl, progress } = active;
 
   const { crop, aspect, showGrid, imgDimensions } = cropState;
 
@@ -44,6 +58,17 @@ export function CropSettings({
   const [customW, setCustomW] = useState("3");
   const [customH, setCustomH] = useState("2");
 
+  // Content-aware extension state
+  const [extendTop, setExtendTop] = useState(0);
+  const [extendRight, setExtendRight] = useState(0);
+  const [extendBottom, setExtendBottom] = useState(0);
+  const [extendLeft, setExtendLeft] = useState(0);
+
+  // Notify parent when mode changes
+  useEffect(() => {
+    onModeChange?.(mode);
+  }, [mode, onModeChange]);
+
   // Convert percentage crop to pixel values
   const toPixels = useCallback(
     (c: Crop) => {
@@ -180,7 +205,7 @@ export function CropSettings({
         height: Math.max(0.1, crop.height),
         unit: "percent" as const,
       };
-      processAllFiles(files, settings);
+      standardCrop.processAllFiles(files, settings);
     } else {
       const settings = {
         left: pixels.left,
@@ -188,16 +213,60 @@ export function CropSettings({
         width: Math.max(1, pixels.width),
         height: Math.max(1, pixels.height),
       };
-      processFiles(files, settings);
+      standardCrop.processFiles(files, settings);
+    }
+  };
+
+  const handleExtendPreset = useCallback(
+    (targetAspect: number) => {
+      if (!imgDimensions) return;
+      const { width: w, height: h } = imgDimensions;
+      const currentAspect = w / h;
+      let top = 0;
+      let right = 0;
+      let bottom = 0;
+      let left = 0;
+      if (targetAspect > currentAspect) {
+        // Need wider -- extend left and right
+        const newWidth = Math.round(h * targetAspect);
+        const extra = newWidth - w;
+        left = Math.round(extra / 2);
+        right = extra - left;
+      } else {
+        // Need taller -- extend top and bottom
+        const newHeight = Math.round(w / targetAspect);
+        const extra = newHeight - h;
+        top = Math.round(extra / 2);
+        bottom = extra - top;
+      }
+      setExtendTop(top);
+      setExtendRight(right);
+      setExtendBottom(bottom);
+      setExtendLeft(left);
+    },
+    [imgDimensions],
+  );
+
+  const handleContentAwareProcess = () => {
+    const settings = { extendTop, extendRight, extendBottom, extendLeft };
+    if (files.length > 1) {
+      contentAwareCrop.processAllFiles(files, settings);
+    } else {
+      contentAwareCrop.processFiles(files, settings);
     }
   };
 
   const hasFile = files.length > 0;
   const hasSize = pixels.width > 0 && pixels.height > 0;
+  const hasExtension = extendTop > 0 || extendRight > 0 || extendBottom > 0 || extendLeft > 0;
 
   const handleSubmit = (e: React.FormEvent) => {
     e.preventDefault();
-    if (hasFile && hasSize && !processing) handleProcess();
+    if (mode === "content-aware") {
+      if (hasFile && hasExtension && !processing) handleContentAwareProcess();
+    } else {
+      if (hasFile && hasSize && !processing) handleProcess();
+    }
   };
 
   // Find which preset label matches the current aspect
@@ -209,155 +278,280 @@ export function CropSettings({
     return false;
   })?.label;
 
+  const canSubmit =
+    mode === "content-aware"
+      ? hasFile && hasExtension && !processing
+      : hasFile && hasSize && !processing;
+
   return (
     <form onSubmit={handleSubmit} className="space-y-4" data-crop-form>
-      {/* Aspect Ratio */}
-      <div>
-        <div className="flex items-center justify-between mb-1">
-          <p className="text-xs text-muted-foreground">Aspect Ratio</p>
-          {aspect !== undefined && (
-            <button
-              type="button"
-              onClick={handleSwapAspect}
-              className="p-1 rounded hover:bg-muted text-muted-foreground hover:text-foreground"
-              title="Swap width/height"
-            >
-              <ArrowLeftRight className="h-3.5 w-3.5" />
-            </button>
+      {/* Mode tabs */}
+      <div className="flex gap-1 mb-4">
+        <button
+          type="button"
+          onClick={() => setMode("standard")}
+          className={`flex-1 text-xs py-1.5 rounded ${
+            mode === "standard"
+              ? "bg-primary text-primary-foreground"
+              : "bg-muted text-muted-foreground"
+          }`}
+        >
+          Standard
+        </button>
+        <button
+          type="button"
+          onClick={() => setMode("content-aware")}
+          className={`flex-1 text-xs py-1.5 rounded ${
+            mode === "content-aware"
+              ? "bg-primary text-primary-foreground"
+              : "bg-muted text-muted-foreground"
+          }`}
+        >
+          Content-Aware
+        </button>
+      </div>
+
+      {/* Standard tab */}
+      {mode === "standard" && (
+        <>
+          {/* Aspect Ratio */}
+          <div>
+            <div className="flex items-center justify-between mb-1">
+              <p className="text-xs text-muted-foreground">Aspect Ratio</p>
+              {aspect !== undefined && (
+                <button
+                  type="button"
+                  onClick={handleSwapAspect}
+                  className="p-1 rounded hover:bg-muted text-muted-foreground hover:text-foreground"
+                  title="Swap width/height"
+                >
+                  <ArrowLeftRight className="h-3.5 w-3.5" />
+                </button>
+              )}
+            </div>
+            <div className="flex flex-wrap gap-1">
+              {ASPECT_PRESETS.map(({ label, value }) => (
+                <button
+                  type="button"
+                  key={label}
+                  onClick={() => handleAspectSelect(value)}
+                  className={`px-2 py-1.5 rounded text-xs transition-colors ${
+                    !customMode && activePresetLabel === label
+                      ? "bg-primary text-primary-foreground"
+                      : "bg-muted text-muted-foreground hover:bg-primary/20 hover:text-foreground"
+                  }`}
+                >
+                  {label}
+                </button>
+              ))}
+              <button
+                type="button"
+                onClick={handleCustomSelect}
+                className={`px-2 py-1.5 rounded text-xs transition-colors ${
+                  customMode
+                    ? "bg-primary text-primary-foreground"
+                    : "bg-muted text-muted-foreground hover:bg-primary/20 hover:text-foreground"
+                }`}
+              >
+                Custom
+              </button>
+            </div>
+            {customMode && (
+              <div className="flex items-center gap-1.5 mt-2">
+                <input
+                  type="number"
+                  value={customW}
+                  onChange={(e) => {
+                    setCustomW(e.target.value);
+                    const w = Number(e.target.value);
+                    const h = Number(customH);
+                    if (w > 0 && h > 0) applyCustomAspect(w, h);
+                  }}
+                  min={1}
+                  className="w-16 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums text-center"
+                />
+                <span className="text-xs text-muted-foreground">:</span>
+                <input
+                  type="number"
+                  value={customH}
+                  onChange={(e) => {
+                    setCustomH(e.target.value);
+                    const w = Number(customW);
+                    const h = Number(e.target.value);
+                    if (w > 0 && h > 0) applyCustomAspect(w, h);
+                  }}
+                  min={1}
+                  className="w-16 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums text-center"
+                />
+              </div>
+            )}
+          </div>
+
+          {/* Position & Size */}
+          <div>
+            <p className="text-xs text-muted-foreground">Position & Size</p>
+            <div className="grid grid-cols-2 gap-2 mt-1">
+              <div>
+                <label htmlFor="crop-x" className="text-[10px] text-muted-foreground">
+                  X{imgDimensions ? ` (of ${imgDimensions.width})` : ""}
+                </label>
+                <input
+                  id="crop-x"
+                  type="number"
+                  value={pixels.left}
+                  onChange={(e) => handlePixelChange("left", Number(e.target.value))}
+                  min={0}
+                  max={imgDimensions ? imgDimensions.width - 1 : undefined}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+              <div>
+                <label htmlFor="crop-y" className="text-[10px] text-muted-foreground">
+                  Y{imgDimensions ? ` (of ${imgDimensions.height})` : ""}
+                </label>
+                <input
+                  id="crop-y"
+                  type="number"
+                  value={pixels.top}
+                  onChange={(e) => handlePixelChange("top", Number(e.target.value))}
+                  min={0}
+                  max={imgDimensions ? imgDimensions.height - 1 : undefined}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+              <div>
+                <label htmlFor="crop-width" className="text-[10px] text-muted-foreground">
+                  Width{imgDimensions ? ` (of ${imgDimensions.width})` : ""}
+                </label>
+                <input
+                  id="crop-width"
+                  type="number"
+                  value={pixels.width}
+                  onChange={(e) => handlePixelChange("width", Number(e.target.value))}
+                  min={1}
+                  max={imgDimensions ? imgDimensions.width : undefined}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+              <div>
+                <label htmlFor="crop-height" className="text-[10px] text-muted-foreground">
+                  Height{imgDimensions ? ` (of ${imgDimensions.height})` : ""}
+                </label>
+                <input
+                  id="crop-height"
+                  type="number"
+                  value={pixels.height}
+                  onChange={(e) => handlePixelChange("height", Number(e.target.value))}
+                  min={1}
+                  max={imgDimensions ? imgDimensions.height : undefined}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+            </div>
+          </div>
+
+          {/* Grid overlay toggle */}
+          <label className="flex items-center gap-2 w-full px-2 py-1.5 rounded text-xs cursor-pointer select-none text-muted-foreground hover:text-foreground transition-colors">
+            <input
+              type="checkbox"
+              checked={showGrid}
+              onChange={(e) => onGridToggle(e.target.checked)}
+              className="accent-primary h-3.5 w-3.5"
+            />
+            <Grid3x3 className="h-3.5 w-3.5" />
+            Rule of Thirds
+          </label>
+        </>
+      )}
+
+      {/* Content-Aware tab */}
+      {mode === "content-aware" && (
+        <div className="space-y-4">
+          {/* Aspect ratio presets */}
+          <div>
+            <p className="text-xs text-muted-foreground mb-1">Extend to aspect ratio</p>
+            <div className="flex flex-wrap gap-1">
+              {EXTEND_PRESETS.map(({ label, aspect: a }) => (
+                <button
+                  key={label}
+                  type="button"
+                  onClick={() => handleExtendPreset(a)}
+                  className="px-2 py-1.5 rounded text-xs bg-muted text-muted-foreground hover:bg-primary/20 hover:text-foreground transition-colors"
+                >
+                  {label}
+                </button>
+              ))}
+            </div>
+          </div>
+
+          {/* Per-side extension */}
+          <div>
+            <p className="text-xs text-muted-foreground mb-1">Extend by (pixels)</p>
+            <div className="grid grid-cols-2 gap-2">
+              <div>
+                <label htmlFor="extend-top" className="text-[10px] text-muted-foreground">
+                  Top
+                </label>
+                <input
+                  id="extend-top"
+                  type="number"
+                  value={extendTop}
+                  onChange={(e) => setExtendTop(Math.max(0, Number(e.target.value)))}
+                  min={0}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+              <div>
+                <label htmlFor="extend-right" className="text-[10px] text-muted-foreground">
+                  Right
+                </label>
+                <input
+                  id="extend-right"
+                  type="number"
+                  value={extendRight}
+                  onChange={(e) => setExtendRight(Math.max(0, Number(e.target.value)))}
+                  min={0}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+              <div>
+                <label htmlFor="extend-bottom" className="text-[10px] text-muted-foreground">
+                  Bottom
+                </label>
+                <input
+                  id="extend-bottom"
+                  type="number"
+                  value={extendBottom}
+                  onChange={(e) => setExtendBottom(Math.max(0, Number(e.target.value)))}
+                  min={0}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+              <div>
+                <label htmlFor="extend-left" className="text-[10px] text-muted-foreground">
+                  Left
+                </label>
+                <input
+                  id="extend-left"
+                  type="number"
+                  value={extendLeft}
+                  onChange={(e) => setExtendLeft(Math.max(0, Number(e.target.value)))}
+                  min={0}
+                  className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
+                />
+              </div>
+            </div>
+          </div>
+
+          {/* Output size display */}
+          {imgDimensions && (
+            <p className="text-xs text-muted-foreground">
+              New size: {imgDimensions.width + extendLeft + extendRight} x{" "}
+              {imgDimensions.height + extendTop + extendBottom}
+            </p>
           )}
         </div>
-        <div className="flex flex-wrap gap-1">
-          {ASPECT_PRESETS.map(({ label, value }) => (
-            <button
-              type="button"
-              key={label}
-              onClick={() => handleAspectSelect(value)}
-              className={`px-2 py-1.5 rounded text-xs transition-colors ${
-                !customMode && activePresetLabel === label
-                  ? "bg-primary text-primary-foreground"
-                  : "bg-muted text-muted-foreground hover:bg-primary/20 hover:text-foreground"
-              }`}
-            >
-              {label}
-            </button>
-          ))}
-          <button
-            type="button"
-            onClick={handleCustomSelect}
-            className={`px-2 py-1.5 rounded text-xs transition-colors ${
-              customMode
-                ? "bg-primary text-primary-foreground"
-                : "bg-muted text-muted-foreground hover:bg-primary/20 hover:text-foreground"
-            }`}
-          >
-            Custom
-          </button>
-        </div>
-        {customMode && (
-          <div className="flex items-center gap-1.5 mt-2">
-            <input
-              type="number"
-              value={customW}
-              onChange={(e) => {
-                setCustomW(e.target.value);
-                const w = Number(e.target.value);
-                const h = Number(customH);
-                if (w > 0 && h > 0) applyCustomAspect(w, h);
-              }}
-              min={1}
-              className="w-16 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums text-center"
-            />
-            <span className="text-xs text-muted-foreground">:</span>
-            <input
-              type="number"
-              value={customH}
-              onChange={(e) => {
-                setCustomH(e.target.value);
-                const w = Number(customW);
-                const h = Number(e.target.value);
-                if (w > 0 && h > 0) applyCustomAspect(w, h);
-              }}
-              min={1}
-              className="w-16 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums text-center"
-            />
-          </div>
-        )}
-      </div>
-
-      {/* Position & Size */}
-      <div>
-        <p className="text-xs text-muted-foreground">Position & Size</p>
-        <div className="grid grid-cols-2 gap-2 mt-1">
-          <div>
-            <label htmlFor="crop-x" className="text-[10px] text-muted-foreground">
-              X{imgDimensions ? ` (of ${imgDimensions.width})` : ""}
-            </label>
-            <input
-              id="crop-x"
-              type="number"
-              value={pixels.left}
-              onChange={(e) => handlePixelChange("left", Number(e.target.value))}
-              min={0}
-              max={imgDimensions ? imgDimensions.width - 1 : undefined}
-              className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
-            />
-          </div>
-          <div>
-            <label htmlFor="crop-y" className="text-[10px] text-muted-foreground">
-              Y{imgDimensions ? ` (of ${imgDimensions.height})` : ""}
-            </label>
-            <input
-              id="crop-y"
-              type="number"
-              value={pixels.top}
-              onChange={(e) => handlePixelChange("top", Number(e.target.value))}
-              min={0}
-              max={imgDimensions ? imgDimensions.height - 1 : undefined}
-              className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
-            />
-          </div>
-          <div>
-            <label htmlFor="crop-width" className="text-[10px] text-muted-foreground">
-              Width{imgDimensions ? ` (of ${imgDimensions.width})` : ""}
-            </label>
-            <input
-              id="crop-width"
-              type="number"
-              value={pixels.width}
-              onChange={(e) => handlePixelChange("width", Number(e.target.value))}
-              min={1}
-              max={imgDimensions ? imgDimensions.width : undefined}
-              className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
-            />
-          </div>
-          <div>
-            <label htmlFor="crop-height" className="text-[10px] text-muted-foreground">
-              Height{imgDimensions ? ` (of ${imgDimensions.height})` : ""}
-            </label>
-            <input
-              id="crop-height"
-              type="number"
-              value={pixels.height}
-              onChange={(e) => handlePixelChange("height", Number(e.target.value))}
-              min={1}
-              max={imgDimensions ? imgDimensions.height : undefined}
-              className="w-full mt-0.5 px-2 py-1.5 rounded border border-border bg-background text-sm text-foreground tabular-nums"
-            />
-          </div>
-        </div>
-      </div>
-
-      {/* Grid overlay toggle */}
-      <label className="flex items-center gap-2 w-full px-2 py-1.5 rounded text-xs cursor-pointer select-none text-muted-foreground hover:text-foreground transition-colors">
-        <input
-          type="checkbox"
-          checked={showGrid}
-          onChange={(e) => onGridToggle(e.target.checked)}
-          className="accent-primary h-3.5 w-3.5"
-        />
-        <Grid3x3 className="h-3.5 w-3.5" />
-        Rule of Thirds
-      </label>
+      )}
 
       {/* Error */}
       {error && <p className="text-xs text-red-500">{error}</p>}
@@ -367,7 +561,7 @@ export function CropSettings({
         <ProgressCard
           active={processing}
           phase={progress.phase === "idle" ? "uploading" : progress.phase}
-          label="Cropping"
+          label={mode === "content-aware" ? "Extending" : "Cropping"}
           stage={progress.stage}
           percent={progress.percent}
           elapsed={progress.elapsed}
@@ -376,10 +570,16 @@ export function CropSettings({
         <button
           type="submit"
           data-testid="crop-submit"
-          disabled={!hasFile || !hasSize || processing}
+          disabled={!canSubmit}
           className="w-full py-2.5 rounded-lg bg-primary text-primary-foreground font-medium disabled:opacity-50 disabled:cursor-not-allowed flex items-center justify-center gap-2"
         >
-          {files.length > 1 ? `Crop (${files.length} files)` : "Crop"}
+          {mode === "content-aware"
+            ? files.length > 1
+              ? `Extend (${files.length} files)`
+              : "Extend"
+            : files.length > 1
+              ? `Crop (${files.length} files)`
+              : "Crop"}
         </button>
       )}