diff --git a/app/Support/RetryHttpConnectionFailures.php b/app/Support/RetryHttpConnectionFailures.php
index 1ab42313a0..dbb6409263 100644
--- a/app/Support/RetryHttpConnectionFailures.php
+++ b/app/Support/RetryHttpConnectionFailures.php
@@ -13,6 +13,8 @@ use Throwable;
  * Guzzle middleware that sends a request again once after a connection failure.
  * cURL counts the DNS lookup in the connect timeout, and a lost DNS query waits 5 seconds before the resolver tries again.
  * Only idempotent methods are retried, because a POST or PATCH can reach the server before the timeout.
+ * Guzzle also reports a timeout while waiting for the response as a connection failure; that request reached
+ * the server and already waited the full timeout, so it is not sent again.
  */
 class RetryHttpConnectionFailures
 {
@@ -22,7 +24,7 @@ class RetryHttpConnectionFailures
     {
         return function (RequestInterface $request, array $options) use ($handler): PromiseInterface {
             return $this->send($handler, $request, $options)->otherwise(function (Throwable $exception) use ($handler, $request, $options): PromiseInterface {
-                if (! $exception instanceof ConnectException || ! in_array($request->getMethod(), self::RETRIED_METHODS, true)) {
+                if (! $exception instanceof ConnectException || $this->timedOutAfterSending($exception) || ! in_array($request->getMethod(), self::RETRIED_METHODS, true)) {
                     return Create::rejectionFor($exception);
                 }
 
@@ -33,6 +35,13 @@ class RetryHttpConnectionFailures
         };
     }
 
+    private function timedOutAfterSending(ConnectException $exception): bool
+    {
+        $context = $exception->getHandlerContext();
+
+        return ($context['errno'] ?? null) === CURLE_OPERATION_TIMEDOUT && ($context['request_size'] ?? 0) > 0;
+    }
+
     /**
      * The cURL handler rejects the promise on a connection failure, but other handlers (such as Http::fake()) throw.
      */
diff --git a/tests/Feature/HttpConnectionRetryTest.php b/tests/Feature/HttpConnectionRetryTest.php
index 58543a1387..58dedddf64 100644
--- a/tests/Feature/HttpConnectionRetryTest.php
+++ b/tests/Feature/HttpConnectionRetryTest.php
@@ -38,3 +38,20 @@ test('a post request is not retried because the server can have received it', fu
     expect(fn () => Http::post('https://api.example.com/items'))->toThrow(ConnectionException::class)
         ->and($this->attempts)->toBe(1);
 });
+
+test('a read request is not sent again after it timed out waiting for the response', function () {
+    $server = stream_socket_server('tcp://127.0.0.1:0');
+    $address = stream_socket_get_name($server, false);
+
+    expect(fn () => Http::timeout(1)->get("http://{$address}/slow"))
+        ->toThrow(ConnectionException::class, 'cURL error 28');
+
+    stream_set_blocking($server, false);
+    $connections = 0;
+    while (@stream_socket_accept($server, 0)) {
+        $connections++;
+    }
+    fclose($server);
+
+    expect($connections)->toBe(1);
+});