diff --git a/platforms/android/lib/src/main/java/com/shopify/checkoutkit/CheckoutWebView.kt b/platforms/android/lib/src/main/java/com/shopify/checkoutkit/CheckoutWebView.kt
index 50a894fcf..26ea384d1 100644
--- a/platforms/android/lib/src/main/java/com/shopify/checkoutkit/CheckoutWebView.kt
+++ b/platforms/android/lib/src/main/java/com/shopify/checkoutkit/CheckoutWebView.kt
@@ -270,29 +270,57 @@ internal class CheckoutWebView private constructor(
             errorResponse: WebResourceResponse?
         ) {
             val isMainFrame = request?.isForMainFrame == true
-            if (isMainFrame) {
-                val statusCode = errorResponse?.statusCode ?: 0
-                preloadCache.evict(
-                    PreloadState.Failed(
-                        PreloadState.FailureReason.HttpError(statusCode),
-                        "HTTP response returned status code $statusCode.",
-                    ),
-                    view = this@CheckoutWebView,
-                )
+            val statusCode = errorResponse?.statusCode ?: 0
+            val failureReason = PreloadState.FailureReason.HttpError(statusCode)
+            val failureMessage = "HTTP response returned status code $statusCode."
+
+            if (errorResponse.isCloudflareManagedChallenge()) {
+                if (isMainFrame && preloadCache.contains(this@CheckoutWebView) && !isPresented) {
+                    log.d(LOG_TAG, "Discarding cached Cloudflare managed challenge response.")
+                    stopLoading()
+                    evictForTerminalFailure(
+                        this@CheckoutWebView,
+                        failureReason,
+                        failureMessage,
+                    )
+                } else {
+                    log.d(LOG_TAG, "Allowing Cloudflare managed challenge response to render.")
+                }
+            } else {
+                if (isMainFrame) {
+                    preloadCache.evict(
+                        PreloadState.Failed(
+                            failureReason,
+                            failureMessage,
+                        ),
+                        view = this@CheckoutWebView,
+                    )
+                }
+                errorResponse?.let {
+                    handleHttpError(
+                        request,
+                        it.statusCode,
+                        it.reasonPhrase.ifBlank { "HTTP ${it.statusCode} Error" },
+                    )
+                }
             }
             super.onReceivedHttpError(view, request, errorResponse)
-            errorResponse?.let {
-                handleHttpError(
-                    request,
-                    it.statusCode,
-                    it.reasonPhrase.ifBlank { "HTTP ${it.statusCode} Error" },
-                )
-            }
             if (isMainFrame) {
                 resetCheckoutRequestRetryState()
             }
         }
 
+        private fun WebResourceResponse?.isCloudflareManagedChallenge(): Boolean {
+            val mitigation = this
+                ?.responseHeaders
+                ?.entries
+                ?.firstOrNull { (name) -> name.equals("cf-mitigated", ignoreCase = true) }
+                ?.value
+                ?.trim()
+
+            return mitigation.equals("challenge", ignoreCase = true)
+        }
+
         override fun shouldOverrideUrlLoading(
             view: WebView?,
             request: WebResourceRequest?
diff --git a/platforms/android/lib/src/test/java/com/shopify/checkoutkit/PreloadObservabilityTest.kt b/platforms/android/lib/src/test/java/com/shopify/checkoutkit/PreloadObservabilityTest.kt
index c22e5ecbd..12be03590 100644
--- a/platforms/android/lib/src/test/java/com/shopify/checkoutkit/PreloadObservabilityTest.kt
+++ b/platforms/android/lib/src/test/java/com/shopify/checkoutkit/PreloadObservabilityTest.kt
@@ -13,6 +13,7 @@ import org.junit.Before
 import org.junit.Test
 import org.junit.runner.RunWith
 import org.mockito.kotlin.mock
+import org.mockito.kotlin.verifyNoInteractions
 import org.mockito.kotlin.whenever
 import org.robolectric.Robolectric
 import org.robolectric.RobolectricTestRunner
@@ -349,6 +350,7 @@ class PreloadObservabilityTest {
         val response = mock<WebResourceResponse> {
             whenever(it.statusCode).thenReturn(500)
             whenever(it.reasonPhrase).thenReturn("Internal Server Error")
+            whenever(it.responseHeaders).thenReturn(mapOf("cf-mitigated" to "block"))
         }
         shadowOf(view).webViewClient.onReceivedHttpError(view, request, response)
         ShadowLooper.shadowMainLooper().idle()
@@ -362,6 +364,117 @@ class PreloadObservabilityTest {
             )
     }
 
+    @Test
+    fun `cloudflare managed challenge discards backgrounded preload without checkout failure`() {
+        val preload = ShopifyCheckoutKit.preload(url, activity, webMessageTransport)!!
+        ShadowLooper.shadowMainLooper().idle()
+        val view = CheckoutWebView.cachedPreloadViewForTesting()!!
+        val listener = mock<CheckoutWebViewListener>()
+        view.setListener(listener)
+        val request = mock<WebResourceRequest> {
+            whenever(it.isForMainFrame).thenReturn(true)
+            whenever(it.url).thenReturn(Uri.parse(url))
+        }
+        val response = mock<WebResourceResponse> {
+            whenever(it.statusCode).thenReturn(403)
+            whenever(it.reasonPhrase).thenReturn("Forbidden")
+            whenever(it.responseHeaders).thenReturn(mapOf("CF-MITIGATED" to "  ChAlLeNgE\t"))
+        }
+
+        shadowOf(view).webViewClient.onReceivedHttpError(view, request, response)
+        ShadowLooper.shadowMainLooper().idle()
+
+        assertThat(preload.state)
+            .isEqualTo(
+                PreloadState.Failed(
+                    PreloadState.FailureReason.HttpError(403),
+                    "HTTP response returned status code 403.",
+                ),
+            )
+        assertThat(CheckoutWebView.cachedPreloadViewForTesting()).isNull()
+        verifyNoInteractions(listener)
+    }
+
+    @Test
+    fun `cloudflare managed challenge renders for presented preload`() {
+        val preload = ShopifyCheckoutKit.preload(url, activity, webMessageTransport)!!
+        ShadowLooper.shadowMainLooper().idle()
+        val view = CheckoutWebView.checkoutViewFor(url, activity, webMessageTransport)
+        view.markPresented()
+        val listener = mock<CheckoutWebViewListener>()
+        view.setListener(listener)
+        val request = mock<WebResourceRequest> {
+            whenever(it.isForMainFrame).thenReturn(true)
+            whenever(it.url).thenReturn(Uri.parse(url))
+        }
+        val response = mock<WebResourceResponse> {
+            whenever(it.statusCode).thenReturn(403)
+            whenever(it.reasonPhrase).thenReturn("Forbidden")
+            whenever(it.responseHeaders).thenReturn(mapOf("cf-mitigated" to "challenge"))
+        }
+
+        shadowOf(view).webViewClient.onReceivedHttpError(view, request, response)
+        ShadowLooper.shadowMainLooper().idle()
+
+        assertThat(preload.state).isEqualTo(PreloadState.Loading)
+        assertThat(CheckoutWebView.cachedPreloadViewForTesting()).isSameAs(view)
+        verifyNoInteractions(listener)
+    }
+
+    @Test
+    fun `cloudflare subframe challenge does not discard backgrounded preload`() {
+        val preload = ShopifyCheckoutKit.preload(url, activity, webMessageTransport)!!
+        ShadowLooper.shadowMainLooper().idle()
+        val view = CheckoutWebView.cachedPreloadViewForTesting()!!
+        val listener = mock<CheckoutWebViewListener>()
+        view.setListener(listener)
+        val request = mock<WebResourceRequest> {
+            whenever(it.isForMainFrame).thenReturn(false)
+            whenever(it.url).thenReturn(Uri.parse(url))
+        }
+        val response = mock<WebResourceResponse> {
+            whenever(it.statusCode).thenReturn(403)
+            whenever(it.reasonPhrase).thenReturn("Forbidden")
+            whenever(it.responseHeaders).thenReturn(mapOf("cf-mitigated" to "challenge"))
+        }
+
+        shadowOf(view).webViewClient.onReceivedHttpError(view, request, response)
+        ShadowLooper.shadowMainLooper().idle()
+
+        assertThat(preload.state).isEqualTo(PreloadState.Loading)
+        assertThat(CheckoutWebView.cachedPreloadViewForTesting()).isSameAs(view)
+        verifyNoInteractions(listener)
+    }
+
+    @Test
+    fun `cloudflare managed challenge discards dismissed cached view without checkout failure`() {
+        val preload = ShopifyCheckoutKit.preload(url, activity, webMessageTransport)!!
+        ShadowLooper.shadowMainLooper().idle()
+        val view = CheckoutWebView.checkoutViewFor(url, activity, webMessageTransport)
+        view.markPresented()
+        assertThat(CheckoutWebView.retainAfterPresentation(view)).isTrue()
+        assertThat(view.isPresented).isFalse()
+        assertThat(view.isPreloadRequest).isFalse()
+        val listener = mock<CheckoutWebViewListener>()
+        view.setListener(listener)
+        val request = mock<WebResourceRequest> {
+            whenever(it.isForMainFrame).thenReturn(true)
+            whenever(it.url).thenReturn(Uri.parse(url))
+        }
+        val response = mock<WebResourceResponse> {
+            whenever(it.statusCode).thenReturn(403)
+            whenever(it.reasonPhrase).thenReturn("Forbidden")
+            whenever(it.responseHeaders).thenReturn(mapOf("cf-mitigated" to "challenge"))
+        }
+
+        shadowOf(view).webViewClient.onReceivedHttpError(view, request, response)
+        ShadowLooper.shadowMainLooper().idle()
+
+        assertThat(preload.state).isEqualTo(PreloadState.Loading)
+        assertThat(CheckoutWebView.cachedPreloadViewForTesting()).isNull()
+        verifyNoInteractions(listener)
+    }
+
     @Test
     fun `http failure callback can start a replacement preload`() {
         val replacementStates = mutableListOf<PreloadState>()