diff --git a/extensions/cornerstone-dicom-seg/src/components/LogicalContourOperationsOptions.tsx b/extensions/cornerstone-dicom-seg/src/components/LogicalContourOperationsOptions.tsx
index e0abd2ede..6183dd2d6 100644
--- a/extensions/cornerstone-dicom-seg/src/components/LogicalContourOperationsOptions.tsx
+++ b/extensions/cornerstone-dicom-seg/src/components/LogicalContourOperationsOptions.tsx
@@ -70,7 +70,10 @@ function SegmentSelector({
         onValueChange={onValueChange}
         value={value}
       >
-        <SelectTrigger className="overflow-hidden">
+        <SelectTrigger
+          className="overflow-hidden"
+          data-cy={`logical-contour-segment-${label.toLowerCase()}-trigger`}
+        >
           <SelectValue placeholder={t(placeholder)} />
         </SelectTrigger>
         <SelectContent>
@@ -180,6 +183,7 @@ function LogicalContourOperationOptions() {
                     value={value}
                     key={`logical-contour-operation-${value}`}
                     onClick={() => setOperation(option)}
+                    data-cy={`logical-contour-operation-${value}`}
                   >
                     <Icons.ByName name={icon}></Icons.ByName>
                   </TabsTrigger>
@@ -207,6 +211,7 @@ function LogicalContourOperationOptions() {
       />
       <div className="flex justify-end pl-[34px]">
         <Button
+          data-cy="apply-logical-contour-operation"
           className="border-primary/60 grow border"
           variant="ghost"
           onClick={() => {
@@ -221,6 +226,7 @@ function LogicalContourOperationOptions() {
         <div className="flex items-center justify-start gap-2">
           <Switch
             id="logical-contour-operations-create-new-segment-switch"
+            data-cy="logical-contour-create-new-segment-switch"
             onCheckedChange={setCreateNewSegment}
           ></Switch>
           <Label htmlFor="logical-contour-operations-create-new-segment-switch">
diff --git a/platform/ui-next/src/components/SegmentationTable/SegmentationTableConfig.tsx b/platform/ui-next/src/components/SegmentationTable/SegmentationTableConfig.tsx
index 08aebbbf9..b98fb6b50 100644
--- a/platform/ui-next/src/components/SegmentationTable/SegmentationTableConfig.tsx
+++ b/platform/ui-next/src/components/SegmentationTable/SegmentationTableConfig.tsx
@@ -72,13 +72,22 @@ export const SegmentationTableConfig: React.FC<{ children?: React.ReactNode }> =
           }}
         >
           <TabsList>
-            <TabsTrigger value="fill-and-outline">
+            <TabsTrigger
+              value="fill-and-outline"
+              data-cy={`segmentation-config-display-fill-and-outline${dataCyTypeSuffix}`}
+            >
               <Icons.FillAndOutline className="text-primary" />
             </TabsTrigger>
-            <TabsTrigger value="outline">
+            <TabsTrigger
+              value="outline"
+              data-cy={`segmentation-config-display-outline${dataCyTypeSuffix}`}
+            >
               <Icons.OutlineOnly className="text-primary" />
             </TabsTrigger>
-            <TabsTrigger value="fill">
+            <TabsTrigger
+              value="fill"
+              data-cy={`segmentation-config-display-fill${dataCyTypeSuffix}`}
+            >
               <Icons.FillOnly className="text-primary" />
             </TabsTrigger>
           </TabsList>
diff --git a/tests/ContourCombineOperations.spec.ts b/tests/ContourCombineOperations.spec.ts
new file mode 100644
index 000000000..25db8a3de
--- /dev/null
+++ b/tests/ContourCombineOperations.spec.ts
@@ -0,0 +1,118 @@
+import {
+  test,
+  expect,
+  waitForViewportRenderCycle,
+  checkForScreenshot,
+  screenShotPaths,
+  visitStudyAndHydrate,
+} from './utils';
+
+const segments = {
+  bigSphere: 'Big Sphere',
+  smallSphere: 'Small Sphere',
+  result: 'Segment 5',
+} as const;
+
+test.beforeEach(
+  async ({ page, leftPanelPageObject, DOMOverlayPageObject, rightPanelPageObject }) => {
+    const studyInstanceUID = '1.2.840.113619.2.290.3.3767434740.226.1600859119.501';
+
+    await visitStudyAndHydrate({
+      page,
+      leftPanelPageObject,
+      DOMOverlayPageObject,
+      studyInstanceUID,
+      modality: 'RTSTRUCT',
+    });
+  }
+);
+
+test.describe('Intersect operation', () => {
+  test('intersect Big Sphere with Small Sphere (nested, no edge crossing) produces Small Sphere', async ({
+    page,
+    rightPanelPageObject,
+    viewportPageObject,
+  }) => {
+    const contourSegmentationPanel = rightPanelPageObject.contourSegmentationPanel;
+
+    const activeViewport = await viewportPageObject.active;
+    await activeViewport.pane.dblclick();
+
+    await contourSegmentationPanel.config.toggle.click();
+
+    await contourSegmentationPanel.config.display.fillAndOutline();
+
+    await contourSegmentationPanel.panel.segmentByText(segments.bigSphere).click();
+
+    const combineContours = rightPanelPageObject.contourSegmentationPanel.combineContours;
+
+    await combineContours.open();
+    await combineContours.selectOperation('intersect');
+    await combineContours.selectSegmentA(segments.bigSphere);
+    await combineContours.selectSegmentB(segments.smallSphere);
+    await combineContours.enableCreateNewSegment();
+    let viewportRenderCycle = waitForViewportRenderCycle(page);
+    await combineContours.apply();
+    await viewportRenderCycle;
+
+    await expect(contourSegmentationPanel.panel.rows).toHaveCount(5);
+    await expect(contourSegmentationPanel.panel.nthSegment(4).title).toHaveText(segments.result);
+
+    await contourSegmentationPanel.segmentsVisibilityToggle.click();
+
+    viewportRenderCycle = waitForViewportRenderCycle(page);
+    await contourSegmentationPanel.panel.segmentByText(segments.result).toggleVisibility();
+    await viewportRenderCycle;
+
+    await checkForScreenshot(
+      page,
+      viewportPageObject.grid,
+      screenShotPaths.contourCombineOperations.intersectBigSphereSmallSphereResult
+    );
+  });
+});
+
+test.describe('Subtract operation', () => {
+  test('subtract Big Sphere minus Small Sphere (nested, no edge crossing) produces Big Sphere with a hole', async ({
+    page,
+    rightPanelPageObject,
+    viewportPageObject,
+  }) => {
+    const contourSegmentationPanel = rightPanelPageObject.contourSegmentationPanel;
+
+    const activeViewport = await viewportPageObject.active;
+    await activeViewport.pane.dblclick();
+
+    await contourSegmentationPanel.config.toggle.click();
+
+    await contourSegmentationPanel.config.display.fillAndOutline();
+
+    await contourSegmentationPanel.panel.segmentByText(segments.bigSphere).click();
+
+    const combineContours = rightPanelPageObject.contourSegmentationPanel.combineContours;
+
+    await combineContours.open();
+    await combineContours.selectOperation('subtract');
+    await combineContours.selectSegmentA(segments.bigSphere);
+    await combineContours.selectSegmentB(segments.smallSphere);
+    await combineContours.enableCreateNewSegment();
+    let viewportRenderCycle = waitForViewportRenderCycle(page);
+    await combineContours.apply();
+    await viewportRenderCycle;
+
+    await expect(contourSegmentationPanel.panel.rows).toHaveCount(5);
+    await expect(contourSegmentationPanel.panel.nthSegment(4).title).toHaveText(segments.result);
+
+    await contourSegmentationPanel.segmentsVisibilityToggle.click();
+
+    viewportRenderCycle = waitForViewportRenderCycle(page);
+    await contourSegmentationPanel.panel.segmentByText(segments.result).toggleVisibility();
+    await viewportRenderCycle;
+
+    await checkForScreenshot(
+      page,
+      viewportPageObject.grid,
+      screenShotPaths.contourCombineOperations.subtractBigSphereMinusSmallSphereResult
+    );
+  });
+});
diff --git a/tests/pages/RightPanelPageObject.ts b/tests/pages/RightPanelPageObject.ts
index 1d6a7c96b..d107eb942 100644
--- a/tests/pages/RightPanelPageObject.ts
+++ b/tests/pages/RightPanelPageObject.ts
@@ -395,6 +395,54 @@ export class RightPanelPageObject {
           };
         },
       },
+      get config() {
+        const configToggle = page.getByTestId('segmentation-config-toggle-Contour');
+        return {
+          toggle: {
+            locator: configToggle,
+            click: async () => {
+              await configToggle.click();
+            },
+          },
+          display: {
+            fillAndOutline: async () => {
+              await page
+                .getByTestId(`segmentation-config-display-fill-and-outline-Contour`)
+                .click();
+            },
+            outline: async () => {
+              await page.getByTestId(`segmentation-config-display-outline-Contour`).click();
+            },
+            fill: async () => {
+              await page.getByTestId(`segmentation-config-display-fill-Contour`).click();
+            },
+          },
+        };
+      },
+      get combineContours() {
+        return {
+          open: async () => {
+            await page.getByTestId('LogicalContourOperations').click();
+          },
+          selectOperation: async (operation: 'merge' | 'intersect' | 'subtract') => {
+            await page.getByTestId(`logical-contour-operation-${operation}`).click();
+          },
+          selectSegmentA: async (label: string) => {
+            await page.getByTestId('logical-contour-segment-a-trigger').click();
+            await page.getByRole('option', { name: label }).click();
+          },
+          selectSegmentB: async (label: string) => {
+            await page.getByTestId('logical-contour-segment-b-trigger').click();
+            await page.getByRole('option', { name: label }).click();
+          },
+          apply: async () => {
+            await page.getByTestId('apply-logical-contour-operation').click();
+          },
+          enableCreateNewSegment: async () => {
+            await page.getByTestId('logical-contour-create-new-segment-switch').click();
+          },
+        };
+      },
     };
   }
   get labelMapSegmentationPanel() {
diff --git a/tests/screenshots/chromium/ContourCombineOperations.spec.ts/intersectBigSphereSmallSphereResult.png b/tests/screenshots/chromium/ContourCombineOperations.spec.ts/intersectBigSphereSmallSphereResult.png
new file mode 100644
index 000000000..603dbc667
Binary files /dev/null and b/tests/screenshots/chromium/ContourCombineOperations.spec.ts/intersectBigSphereSmallSphereResult.png differ
diff --git a/tests/screenshots/chromium/ContourCombineOperations.spec.ts/subtractBigSphereMinusSmallSphereResult.png b/tests/screenshots/chromium/ContourCombineOperations.spec.ts/subtractBigSphereMinusSmallSphereResult.png
new file mode 100644
index 000000000..c1bcd688c
Binary files /dev/null and b/tests/screenshots/chromium/ContourCombineOperations.spec.ts/subtractBigSphereMinusSmallSphereResult.png differ
diff --git a/tests/utils/screenShotPaths.ts b/tests/utils/screenShotPaths.ts
index 564415d44..e53e36998 100644
--- a/tests/utils/screenShotPaths.ts
+++ b/tests/utils/screenShotPaths.ts
@@ -221,6 +221,10 @@ const screenShotPaths = {
     overlaysDisplayed: 'overlaysDisplayed.png',
     overlaySEGsAndRTDisplayed: 'overlaySEGsAndRTDisplayed.png',
   },
+  contourCombineOperations: {
+    subtractBigSphereMinusSmallSphereResult: 'subtractBigSphereMinusSmallSphereResult.png',
+    intersectBigSphereSmallSphereResult: 'intersectBigSphereSmallSphereResult.png',
+  },
   workList: {
     scrollBarRenderedProperly: 'scrollBarRenderedProperly.png',
   },