diff --git a/src/Illuminate/Http/Client/Factory.php b/src/Illuminate/Http/Client/Factory.php
index 117d1115e2b1..c0d4888fcd0b 100644
--- a/src/Illuminate/Http/Client/Factory.php
+++ b/src/Illuminate/Http/Client/Factory.php
@@ -25,7 +25,7 @@
  * @method \Illuminate\Http\Client\PendingRequest contentType(string $contentType)
  * @method \Illuminate\Http\Client\PendingRequest dd()
  * @method \Illuminate\Http\Client\PendingRequest dump()
- * @method \Illuminate\Http\Client\PendingRequest retry(int $times, int $sleep = 0)
+ * @method \Illuminate\Http\Client\PendingRequest retry(int $times, int $sleep = 0, ?callable $when = null)
  * @method \Illuminate\Http\Client\PendingRequest sink(string|resource $to)
  * @method \Illuminate\Http\Client\PendingRequest stub(callable $callback)
  * @method \Illuminate\Http\Client\PendingRequest timeout(int $seconds)
diff --git a/src/Illuminate/Http/Client/PendingRequest.php b/src/Illuminate/Http/Client/PendingRequest.php
index b09113be0dca..d5426fb09cdd 100644
--- a/src/Illuminate/Http/Client/PendingRequest.php
+++ b/src/Illuminate/Http/Client/PendingRequest.php
@@ -98,6 +98,13 @@ class PendingRequest
      */
     protected $retryDelay = 100;
 
+    /**
+     * The callback that will determine if the request should be retried.
+     *
+     * @var callable|null
+     */
+    protected $retryWhenCallback = null;
+
     /**
      * The callbacks that should execute before the request is sent.
      *
@@ -441,12 +448,14 @@ public function timeout(int $seconds)
      *
      * @param  int  $times
      * @param  int  $sleep
+     * @param  callable|null  $when
      * @return $this
      */
-    public function retry(int $times, int $sleep = 0)
+    public function retry(int $times, int $sleep = 0, ?callable $when = null)
     {
         $this->tries = $times;
         $this->retryDelay = $sleep;
+        $this->retryWhenCallback = $when;
 
         return $this;
     }
@@ -679,7 +688,7 @@ public function send(string $method, string $url, array $options = [])
 
                 throw new ConnectionException($e->getMessage(), 0, $e);
             }
-        }, $this->retryDelay ?? 100);
+        }, $this->retryDelay ?? 100, $this->retryWhenCallback);
     }
 
     /**
diff --git a/src/Illuminate/Support/Facades/Http.php b/src/Illuminate/Support/Facades/Http.php
index 21200c0a5aab..d6f2f6648578 100644
--- a/src/Illuminate/Support/Facades/Http.php
+++ b/src/Illuminate/Support/Facades/Http.php
@@ -20,7 +20,7 @@
  * @method static \Illuminate\Http\Client\PendingRequest contentType(string $contentType)
  * @method static \Illuminate\Http\Client\PendingRequest dd()
  * @method static \Illuminate\Http\Client\PendingRequest dump()
- * @method static \Illuminate\Http\Client\PendingRequest retry(int $times, int $sleep = 0)
+ * @method static \Illuminate\Http\Client\PendingRequest retry(int $times, int $sleep = 0, ?callable $when = null)
  * @method static \Illuminate\Http\Client\PendingRequest sink(string|resource $to)
  * @method static \Illuminate\Http\Client\PendingRequest stub(callable $callback)
  * @method static \Illuminate\Http\Client\PendingRequest timeout(int $seconds)