diff --git a/src/workerd/api/http.c++ b/src/workerd/api/http.c++
index ed24374e413..556fc74249a 100644
--- a/src/workerd/api/http.c++
+++ b/src/workerd/api/http.c++
@@ -1687,11 +1687,35 @@ jsg::Promise<jsg::Ref<Response>> fetchImplNoOutputLock(jsg::Lock& js,
     return ioContext.awaitIo(js,
         AbortSignal::maybeCancelWrap(js, signal, kj::mv(KJ_ASSERT_NONNULL(nativeRequest).response))
             .catch_([](kj::Exception&& exception) -> kj::Promise<kj::HttpClient::Response> {
-      if (exception.getDescription().startsWith("invalid Content-Length header value")) {
+      auto desc = exception.getDescription();
+
+      if (desc.startsWith("invalid Content-Length header value")) {
         return JSG_KJ_EXCEPTION(FAILED, Error, exception.getDescription());
-      } else if (exception.getDescription().contains("NOSENTRY script not found")) {
+      } else if (desc.contains("NOSENTRY script not found")) {
         return JSG_KJ_EXCEPTION(FAILED, Error, "Worker not found.");
       }
+      // Handle TLS certificate validation errors with helpful messages
+      else if (desc.contains("TLS peer's certificate is not trusted")) {
+        return JSG_KJ_EXCEPTION(FAILED, Error,
+            "Network connection failed: The destination server's TLS certificate could not be "
+            "verified. If connecting to a server with a self-signed certificate in local "
+            "development, ensure NODE_EXTRA_CA_CERTS is set to a file containing the CA "
+            "certificate.");
+      } else if (desc.contains("TLS peer provided no certificate")) {
+        return JSG_KJ_EXCEPTION(FAILED, Error,
+            "Network connection failed: The destination server did not provide a TLS "
+            "certificate.");
+      } else if (desc.contains("peer disconnected without gracefully ending TLS session")) {
+        return JSG_KJ_EXCEPTION(FAILED, Error,
+            "Network connection failed: The connection was closed unexpectedly during TLS "
+            "handshake.");
+      } else if (desc.contains("OpenSSL error") || desc.contains("SSL_")) {
+        // Generic TLS/SSL error
+        return JSG_KJ_EXCEPTION(FAILED, Error,
+            "Network connection failed due to a TLS/SSL error. This may indicate a certificate "
+            "configuration issue. In local development, ensure the destination server's CA "
+            "certificate is trusted via NODE_EXTRA_CA_CERTS.");
+      }
       return kj::mv(exception);
     }),
         [fetcher = kj::mv(fetcher), jsRequest = kj::mv(jsRequest), urlList = kj::mv(urlList),
diff --git a/src/workerd/api/tests/fetch-tls-error-test.js b/src/workerd/api/tests/fetch-tls-error-test.js
new file mode 100644
index 00000000000..c98d2a5da2e
--- /dev/null
+++ b/src/workerd/api/tests/fetch-tls-error-test.js
@@ -0,0 +1,39 @@
+// Copyright (c) 2024 Cloudflare, Inc.
+// Licensed under the Apache 2.0 license found in the LICENSE file or at:
+//     https://opensource.org/licenses/Apache-2.0
+
+import assert from 'node:assert';
+
+// Test that TLS errors produce helpful error messages rather than opaque "internal error"
+export const tlsCertificateErrorMessage = {
+  async test(ctrl, env, ctx) {
+    // Attempt to fetch from a server with an untrusted certificate.
+    // The test server uses a self-signed cert that is NOT in the trustedCertificates list
+    // for the internet service, so this should fail with a TLS error.
+
+    try {
+      await fetch(`https://localhost:${env.UNTRUSTED_TLS_PORT}/`);
+      assert.fail('Expected fetch to fail due to TLS certificate error');
+    } catch (err) {
+      // Verify we get a helpful error message, not an opaque internal error
+      assert.ok(
+        !err.message.includes('internal error; reference ='),
+        `Expected helpful TLS error message, got opaque internal error: ${err.message}`
+      );
+
+      // The error should mention TLS/certificate issues and be actionable
+      assert.ok(
+        err.message.includes('TLS') ||
+          err.message.includes('certificate') ||
+          err.message.includes('Network connection failed'),
+        `Expected error message to be helpful about TLS/certificate issues, got: ${err.message}`
+      );
+
+      // Should mention NODE_EXTRA_CA_CERTS as the workaround
+      assert.ok(
+        err.message.includes('NODE_EXTRA_CA_CERTS'),
+        `Expected error message to mention NODE_EXTRA_CA_CERTS workaround, got: ${err.message}`
+      );
+    }
+  },
+};
diff --git a/src/workerd/api/tests/fetch-tls-error-test.wd-test b/src/workerd/api/tests/fetch-tls-error-test.wd-test
new file mode 100644
index 00000000000..75dbc9da355
--- /dev/null
+++ b/src/workerd/api/tests/fetch-tls-error-test.wd-test
@@ -0,0 +1,34 @@
+# Copyright (c) 2024 Cloudflare, Inc.
+# Licensed under the Apache 2.0 license found in the LICENSE file or at:
+#     https://opensource.org/licenses/Apache-2.0
+
+using Workerd = import "/workerd/workerd.capnp";
+
+const config :Workerd.Config = (
+  services = [
+    (
+      name = "main",
+      worker = (
+        modules = [
+          (name = "worker.js", esModule = embed "fetch-tls-error-test.js")
+        ],
+        compatibilityFlags = ["nodejs_compat"],
+        bindings = [
+          (name = "UNTRUSTED_TLS_PORT", fromEnvironment = "UNTRUSTED_TLS_PORT"),
+        ],
+      )
+    ),
+    # Internet service WITHOUT the test server's CA in trustedCertificates.
+    # This simulates the real-world scenario where a certificate is not trusted,
+    # which should trigger the TLS error handling we added.
+    ( name = "internet", 
+      network = ( 
+        allow = ["private"],
+        tlsOptions = (
+          # Intentionally NOT including any trusted certificates to trigger TLS error
+          trustedCertificates = [],
+        ),
+      ) 
+    ),
+  ],
+);