diff --git a/bundles/org.eclipse.swt/Eclipse SWT Tests/win32/org/eclipse/swt/graphics/ImagesWin32Tests.java b/bundles/org.eclipse.swt/Eclipse SWT Tests/win32/org/eclipse/swt/graphics/ImagesWin32Tests.java
index 6b60c2a20df..a7559354653 100644
--- a/bundles/org.eclipse.swt/Eclipse SWT Tests/win32/org/eclipse/swt/graphics/ImagesWin32Tests.java	
+++ b/bundles/org.eclipse.swt/Eclipse SWT Tests/win32/org/eclipse/swt/graphics/ImagesWin32Tests.java	
@@ -1,5 +1,5 @@
 /*******************************************************************************
- * Copyright (c) 2024 Yatta Solutions
+ * Copyright (c) 2024, 2026 Yatta Solutions
  *
  * This program and the accompanying materials
  * are made available under the terms of the Eclipse Public License 2.0
@@ -13,13 +13,18 @@
  *******************************************************************************/
 package org.eclipse.swt.graphics;
 
-import static org.junit.Assert.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertEquals;
+
+import java.util.*;
+import java.util.stream.*;
 
 import org.eclipse.swt.*;
 import org.eclipse.swt.internal.*;
 import org.eclipse.swt.widgets.*;
 import org.junit.jupiter.api.*;
 import org.junit.jupiter.api.extension.*;
+import org.junit.jupiter.params.*;
+import org.junit.jupiter.params.provider.*;
 
 @ExtendWith(PlatformSpecificExecutionExtension.class)
 @ExtendWith(WithMonitorSpecificScalingExtension.class)
@@ -30,9 +35,52 @@ public void testImageIconTypeShouldNotChangeAfterCallingGetHandleForDifferentZoo
 		Image icon = Display.getDefault().getSystemImage(SWT.ICON_ERROR);
 		try {
 			Image.win32_getHandle(icon, 200);
-			assertEquals("Image type should stay to SWT.ICON", SWT.ICON, icon.type);
+			assertEquals(SWT.ICON, icon.type, "Image type should stay to SWT.ICON");
 		} finally {
 			icon.dispose();
 		}
 	}
+
+	/**
+	 * For images with very different width and height (e.g. 500x2), independent
+	 * integer division when computing the zoom from each axis's pixel hint can make the
+	 * height-derived zoom larger than the width-derived zoom. The correct fix is to
+	 * derive the zoom from the axis with the larger pixel hint, which has more pixels
+	 * and therefore a proportionally smaller rounding error.
+	 * <p>
+	 * Verifies that for a wide (500-pixel) image at standard display zoom levels, the
+	 * selected handle width matches the expected width at the requested zoom, across a
+	 * range of image heights where integer-division rounding divergence is most extreme.
+	 */
+	@ParameterizedTest
+	@MethodSource("provideZoomAndHeightCombinations")
+	public void getImageHandle_asymmetricDimensions_selectsCorrectZoom(int displayZoom, int logicalHeight) {
+		Display display = Display.getDefault();
+		int logicalWidth = 500;
+		PaletteData palette = new PaletteData(0xFF0000, 0xFF00, 0xFF);
+		ImageDataProvider provider = zoom -> new ImageData(
+				Math.max(1, Math.round(logicalWidth * zoom / 100f)),
+				Math.max(1, Math.round(logicalHeight * zoom / 100f)),
+				32, palette);
+		Image image = new Image(display, provider);
+		int widthHint = Math.round(logicalWidth * displayZoom / 100f);
+		int heightHint = Math.round(logicalHeight * displayZoom / 100f);
+		int[] capturedWidth = {-1};
+		try {
+			image.executeOnImageHandleAtBestFittingSize(h -> capturedWidth[0] = h.width(), widthHint, heightHint);
+			assertEquals(widthHint, capturedWidth[0],
+					"Handle width should match widthHint for a " + logicalWidth + "x" + logicalHeight
+					+ " image at display zoom " + displayZoom + "%: expected " + widthHint
+					+ " but got " + capturedWidth[0]);
+		} finally {
+			image.dispose();
+		}
+	}
+
+	private static Stream<Arguments> provideZoomAndHeightCombinations() {
+		int[] zooms = { 100, 125, 150, 175, 200 };
+		int[] heights = IntStream.rangeClosed(1, 20).toArray();
+		return Arrays.stream(zooms).boxed()
+				.flatMap(zoom -> Arrays.stream(heights).mapToObj(height -> Arguments.of(zoom, height)));
+	}
 }
diff --git a/bundles/org.eclipse.swt/Eclipse SWT/win32/org/eclipse/swt/graphics/Image.java b/bundles/org.eclipse.swt/Eclipse SWT/win32/org/eclipse/swt/graphics/Image.java
index 12a78ed8464..e229adfe8f0 100644
--- a/bundles/org.eclipse.swt/Eclipse SWT/win32/org/eclipse/swt/graphics/Image.java	
+++ b/bundles/org.eclipse.swt/Eclipse SWT/win32/org/eclipse/swt/graphics/Image.java	
@@ -248,7 +248,7 @@ private InternalImageHandle getOrCreateImageHandleAtClosestSize(int widthHint, i
 			Rectangle bounds = getBounds(100);
 			int imageZoomForWidth = 100 * widthHint / bounds.width;
 			int imageZoomForHeight = 100 * heightHint / bounds.height;
-			int imageZoom = DPIUtil.getZoomForAutoscaleProperty(Math.max(imageZoomForWidth, imageZoomForHeight));
+			int imageZoom = DPIUtil.getZoomForAutoscaleProperty(widthHint > heightHint ? imageZoomForWidth : imageZoomForHeight);
 			InternalImageHandle bestFittingHandle = imageHandleManager.get(imageZoom);
 			if (bestFittingHandle == null) {
 				ImageData bestFittingImageData = imageProvider.loadImageData(imageZoom).element();