diff --git a/chrome/browser/ssl/https_upgrades_browsertest.cc b/chrome/browser/ssl/https_upgrades_browsertest.cc
index c678cf0110cd4..6685011a14d3c 100644
--- a/chrome/browser/ssl/https_upgrades_browsertest.cc
+++ b/chrome/browser/ssl/https_upgrades_browsertest.cc
@@ -1011,6 +1011,46 @@ IN_PROC_BROWSER_TEST_P(HttpsUpgradesBrowserTest,
   EXPECT_EQ(nonexistent_domain, contents->GetLastCommittedURL().host());
 }
 
+// If the upgraded HTTPS URL is not available due to a potentially-transient
+// exempted net error but the hostname is non-unique, don't show the net error
+// page and instead just fallback to HTTP and the HTTPS-First Mode interstitial.
+// Otherwise, the user can be stuck on the net error page when the HTTP version
+// of the host would have resolved, such as for corp single-label hostnames.
+// (Regression test for crbug.com/1451040.)
+IN_PROC_BROWSER_TEST_P(
+    HttpsUpgradesBrowserTest,
+    ExemptNetErrorOnUpgrade_NonUniqueHostname_ShouldFallback) {
+  // This test is only interesting when HTTPS-First Mode is enabled.
+  if (!IsHttpsFirstModePrefEnabled()) {
+    return;
+  }
+
+  GURL http_url = http_server()->GetURL("blorp", "/simple.html");
+  GURL https_url = https_server()->GetURL("blorp", "/simple.html");
+  auto* contents = browser()->tab_strip_model()->GetActiveWebContents();
+
+  // Set up an interceptor that will return ERR_NAME_NOT_RESOLVED. Navigating
+  // to the HTTP URL should get upgraded to HTTPS, and then fallback to HTTP
+  // and the HFM interstitial.
+  auto dns_failure_interceptor =
+      std::make_unique<content::URLLoaderInterceptor>(base::BindRepeating(
+          [](content::URLLoaderInterceptor::RequestParams* params) {
+            params->client->OnComplete(
+                network::URLLoaderCompletionStatus(net::ERR_NAME_NOT_RESOLVED));
+            return true;
+          }));
+  EXPECT_FALSE(content::NavigateToURL(contents, http_url));
+  EXPECT_TRUE(chrome_browser_interstitials::IsShowingInterstitial(contents));
+  ProceedThroughInterstitial(contents);
+
+  // Should now be on the HTTP URL and it should be allowlisted.
+  EXPECT_EQ(http_url, contents->GetLastCommittedURL());
+  Profile* profile = Profile::FromBrowserContext(contents->GetBrowserContext());
+  content::SSLHostStateDelegate* state = profile->GetSSLHostStateDelegate();
+  EXPECT_TRUE(state->IsHttpAllowedForHost(
+      http_url.host(), contents->GetPrimaryMainFrame()->GetStoragePartition()));
+}
+
 // Navigations in subframes should not get upgraded by HTTPS-Only Mode. They
 // should be blocked as mixed content.
 IN_PROC_BROWSER_TEST_P(HttpsUpgradesBrowserTest,
diff --git a/chrome/browser/ssl/https_upgrades_interceptor.cc b/chrome/browser/ssl/https_upgrades_interceptor.cc
index a1e5bbb55ddff..b6a0468c0d2bb 100644
--- a/chrome/browser/ssl/https_upgrades_interceptor.cc
+++ b/chrome/browser/ssl/https_upgrades_interceptor.cc
@@ -587,8 +587,14 @@ bool HttpsUpgradesInterceptor::MaybeCreateLoaderForResponse(
   // enabled, because otherwise these would cause the interstitial to be shown
   // which is confusing. HTTPS-Upgrades will silently fall back to HTTP for
   // these errors.
+  //
+  // However, if this is a request to a non-unique hostname, don't prefer
+  // net error as it is likely non-recoverable -- we want to fallback to HTTP
+  // and the HTTPS-First Mode interstitial in this case. (In particular, this
+  // avoids breaking corporate single-label hostnames.)
   if (IsInterstitialEnabled(*interstitial_state_) &&
-      IsHttpsFirstModeExemptedError(status.error_code)) {
+      IsHttpsFirstModeExemptedError(status.error_code) &&
+      !net::IsHostnameNonUnique(request.url.host())) {
     tab_helper->set_is_exempt_error(true);
     return false;
   }