diff --git a/build/azure-pipelines/common/sanity-tests.yml b/build/azure-pipelines/common/sanity-tests.yml
index ce6d95dd7e5..fdf6b2cd3dd 100644
--- a/build/azure-pipelines/common/sanity-tests.yml
+++ b/build/azure-pipelines/common/sanity-tests.yml
@@ -33,9 +33,9 @@ jobs:
       outputs:
         - output: pipelineArtifact
           targetPath: $(SCREENSHOTS_DIR)
-          artifactName: screenshots-${{ parameters.name }}
+          artifactName: screenshots-${{ parameters.name }}-$(System.JobAttempt)
           displayName: Publish Screenshots
-          condition: succeededOrFailed()
+          condition: and(succeededOrFailed(), eq(variables.HAS_SCREENSHOTS, 'true'))
           continueOnError: true
           sbomEnabled: false
     variables:
@@ -171,6 +171,25 @@ jobs:
           condition: and(succeeded(), ne(variables.DOCKER_CACHE_HIT, 'true'))
           displayName: Save Docker Image
 
+      - ${{ if eq(parameters.os, 'windows') }}:
+        - script: |
+            @echo off
+            dir /b "$(SCREENSHOTS_DIR)" 2>nul | findstr . >nul
+            if %errorlevel%==0 (
+              echo ##vso[task.setvariable variable=HAS_SCREENSHOTS]true
+            )
+            exit /b 0
+          displayName: Check Screenshots
+          condition: succeededOrFailed()
+
+      - ${{ else }}:
+        - bash: |
+            if [ -n "$(ls -A "$(SCREENSHOTS_DIR)" 2>/dev/null)" ]; then
+              echo "##vso[task.setvariable variable=HAS_SCREENSHOTS]true"
+            fi
+          displayName: Check Screenshots
+          condition: succeededOrFailed()
+
       - task: PublishTestResults@2
         inputs:
           testResultsFormat: JUnit
diff --git a/test/sanity/src/context.ts b/test/sanity/src/context.ts
index 62eee018d06..632dae2a534 100644
--- a/test/sanity/src/context.ts
+++ b/test/sanity/src/context.ts
@@ -141,10 +141,19 @@ export class TestContext {
 	public error(message: string): never {
 		const line = `[${new Date().toISOString()}] ERROR: ${message}`;
 		this.consoleOutputs.push(line);
-		console.error(line);
+		console.error(`##vso[task.logissue type=error]${line}`);
 		throw new Error(message);
 	}
 
+	/**
+	 * Logs a warning message with a timestamp.
+	 */
+	public warn(message: string) {
+		const line = `[${new Date().toISOString()}] WARNING: ${message}`;
+		this.consoleOutputs.push(line);
+		console.warn(`##vso[task.logissue type=warning]${line}`);
+	}
+
 	/**
 	 * Creates a new temporary directory and returns its path.
 	 */
@@ -220,7 +229,7 @@ export class TestContext {
 				fs.rmSync(dir, { recursive: true, force: true });
 				this.log(`Deleted temp directory: ${dir}`);
 			} catch (error) {
-				this.log(`Failed to delete temp directory: ${dir}: ${error}`);
+				this.warn(`Failed to delete temp directory: ${dir}: ${error}`);
 			}
 		}
 		this.tempDirs.clear();
@@ -229,7 +238,7 @@ export class TestContext {
 			try {
 				this.deleteWslDir(dir);
 			} catch (error) {
-				this.log(`Failed to delete WSL temp directory: ${dir}: ${error}`);
+				this.warn(`Failed to delete WSL temp directory: ${dir}: ${error}`);
 			}
 		}
 		this.wslTempDirs.clear();
@@ -247,7 +256,7 @@ export class TestContext {
 		for (let attempt = 0; attempt < maxRetries; attempt++) {
 			if (attempt > 0) {
 				const delay = Math.pow(2, attempt - 1) * 1000;
-				this.log(`Retrying fetch (attempt ${attempt + 1}/${maxRetries}) after ${delay}ms`);
+				this.warn(`Retrying fetch (attempt ${attempt + 1}/${maxRetries}) after ${delay}ms`);
 				await new Promise(resolve => setTimeout(resolve, delay));
 			}
 
@@ -266,7 +275,7 @@ export class TestContext {
 				return response as Response & { body: NodeJS.ReadableStream };
 			} catch (error) {
 				lastError = error instanceof Error ? error : new Error(String(error));
-				this.log(`Fetch attempt ${attempt + 1} failed: ${lastError.message}`);
+				this.warn(`Fetch attempt ${attempt + 1} failed: ${lastError.message}`);
 			}
 		}
 
@@ -1091,7 +1100,7 @@ export class TestContext {
 			await page.screenshot({ path: screenshotPath, fullPage: true });
 			this.log(`Screenshot saved to: ${screenshotPath}`);
 		} catch (e) {
-			this.log(`Failed to capture screenshot: ${e instanceof Error ? e.message : String(e)}`);
+			this.warn(`Failed to capture screenshot: ${e instanceof Error ? e.message : String(e)}`);
 		}
 	}
 
diff --git a/test/sanity/src/uiTest.ts b/test/sanity/src/uiTest.ts
index 65f8b14a49e..96733481e96 100644
--- a/test/sanity/src/uiTest.ts
+++ b/test/sanity/src/uiTest.ts
@@ -138,7 +138,7 @@ export class UITest {
 		const extensionItem = page.locator('.extension-list-item').getByText(/^GitHub Pull Requests$/);
 		const messageContainer = page.locator('.extensions-viewlet .message-container:not(.hidden)').first();
 
-		for (let attempt = 0; attempt < 3; attempt++) {
+		for (let attempt = 0; attempt < 5; attempt++) {
 			const result = await Promise.race([
 				extensionItem.waitFor().then(() => 'found' as const),
 				messageContainer.waitFor().then(() => 'message' as const),
@@ -149,20 +149,33 @@ export class UITest {
 			}
 
 			const message = await messageContainer.locator('.message').innerText();
-			this.context.log(`Marketplace message: ${message} (attempt ${attempt + 1}/3), clicking Refresh`);
+			this.context.log(`Marketplace message: ${message} (attempt ${attempt + 1}/5), clicking Refresh`);
 			await page.getByRole('button', { name: 'Refresh' }).click();
-			await messageContainer.waitFor({ state: 'hidden', timeout: 30_000 });
+			await page.waitForTimeout(5_000);
 		}
 
 		await extensionItem.waitFor();
 
-		this.context.log('Clicking Install on the first extension in the list');
-		const installButton = page.locator('.extension-action:not(.disabled)', { hasText: /Install/ }).first();
-		await installButton.waitFor();
-		await installButton.click();
+		for (let attempt = 0; attempt < 3; attempt++) {
+			try {
+				this.context.log(`Clicking Install on the first extension in the list (attempt ${attempt + 1}/3)`);
+				const installButton = page.locator('.extension-action:not(.disabled)', { hasText: /Install/ }).first();
+				await installButton.click();
 
-		this.context.log('Waiting for extension to be installed');
-		await page.getByRole('button', { name: 'Uninstall' }).first().waitFor({ timeout: 5 * 60_000 });
+				this.context.log('Waiting for extension to be installed');
+				const uninstallButton = page.getByRole('button', { name: 'Uninstall' }).first();
+				const installed = await uninstallButton.waitFor({ timeout: 5 * 60_000 }).then(() => true, () => false);
+				if (installed) {
+					return;
+				}
+			} catch (error) {
+				this.context.log(`Extension install attempt ${attempt + 1}/3 failed: ${error instanceof Error ? error.message : String(error)}`);
+			}
+
+			this.context.log('Extension install may have failed, retrying');
+		}
+
+		throw new Error('Failed to install extension after 3 attempts');
 	}
 
 	/**