diff --git a/.changeset/gentle-flags-retry.md b/.changeset/gentle-flags-retry.md
new file mode 100644
index 0000000..8072030
--- /dev/null
+++ b/.changeset/gentle-flags-retry.md
@@ -0,0 +1,5 @@
+---
+'posthog-php': patch
+---
+
+Retry remote feature flag requests after transient 502 and 504 responses.
diff --git a/lib/Client.php b/lib/Client.php
index 4e4b40c..57fee93 100644
--- a/lib/Client.php
+++ b/lib/Client.php
@@ -154,7 +154,7 @@ class Client implements FeatureFlagEvaluationsHost
      * defaults to 5 seconds. For the socket consumer, `timeout` is passed to pfsockopen() and is
      * in seconds.
      *
-     * Feature flag requests to `/flags/?v=2` retry transient curl/network errors only.
+     * Feature flag requests to `/flags/?v=2` retry transient curl/network errors and HTTP 502/504.
      * `feature_flag_request_max_retries` defaults to 1; set it to 0 to disable these retries.
      *
      * @param array{
@@ -1734,9 +1734,8 @@ private function sendFeatureFlagsRequest(array $payload): HttpResponse
             );
 
             if (
-                $httpResponse->getResponseCode() !== 0
-                || $retries >= $this->featureFlagRequestMaxRetries
-                || !$this->isRetryableFlagsCurlError($httpResponse->getCurlErrno())
+                $retries >= $this->featureFlagRequestMaxRetries
+                || !$this->shouldRetryFeatureFlagsRequest($httpResponse)
             ) {
                 return $httpResponse;
             }
@@ -1747,6 +1746,17 @@ private function sendFeatureFlagsRequest(array $payload): HttpResponse
         }
     }
 
+    private function shouldRetryFeatureFlagsRequest(HttpResponse $httpResponse): bool
+    {
+        $responseCode = $httpResponse->getResponseCode();
+
+        if ($responseCode === 0) {
+            return $this->isRetryableFlagsCurlError($httpResponse->getCurlErrno());
+        }
+
+        return $this->isRetryableFlagsStatusCode($responseCode);
+    }
+
     private function isRetryableFlagsCurlError(int $curlErrno): bool
     {
         // Match Ruby's transient subset: timeouts, connection resets/receive failures,
@@ -1754,6 +1764,11 @@ private function isRetryableFlagsCurlError(int $curlErrno): bool
         return in_array($curlErrno, [28, 52, 56], true);
     }
 
+    private function isRetryableFlagsStatusCode(int $statusCode): bool
+    {
+        return in_array($statusCode, [502, 504], true);
+    }
+
     /** @return array{featureFlags: array<string, mixed>, featureFlagPayloads: array<string, mixed>, flags: array<string, mixed>} */
     private function emptyFlagsResponse(): array
     {
diff --git a/lib/PostHog.php b/lib/PostHog.php
index 33a9635..60b823f 100644
--- a/lib/PostHog.php
+++ b/lib/PostHog.php
@@ -31,7 +31,7 @@ class PostHog
      * defaults to 5 seconds. For the socket consumer, `timeout` is passed to pfsockopen() and is
      * in seconds.
      *
-     * Feature flag requests to `/flags/?v=2` retry transient curl/network errors only.
+     * Feature flag requests to `/flags/?v=2` retry transient curl/network errors and HTTP 502/504.
      * `feature_flag_request_max_retries` defaults to 1; set it to 0 to disable these retries.
      *
      * @param array{
diff --git a/test/FeatureFlagTest.php b/test/FeatureFlagTest.php
index 9c699f3..f7aea60 100644
--- a/test/FeatureFlagTest.php
+++ b/test/FeatureFlagTest.php
@@ -81,6 +81,14 @@ public static function nonRetryableFlagsStatusCodes(): array
         ];
     }
 
+    public static function retryableFlagsStatusCodes(): array
+    {
+        return [
+            'bad gateway' => [502],
+            'gateway timeout' => [504],
+        ];
+    }
+
     public static function retryableFlagsCurlErrors(): array
     {
         return [
@@ -233,6 +241,100 @@ public function testFlagsRequestDoesNotRetryHttpStatusErrors(int $statusCode): v
         $this->assertSame('/flags/?v=2', $this->http_client->calls[0]['path']);
     }
 
+    /**
+     * @dataProvider retryableFlagsStatusCodes
+     */
+    public function testFlagsRequestRetriesHttp502And504(int $statusCode): void
+    {
+        $this->http_client = new MockedHttpClient("app.posthog.com");
+        $this->http_client->setFlagsEndpointResponseQueue([
+            ['response' => [], 'responseCode' => $statusCode, 'curlErrno' => 0],
+            ['response' => MockedResponses::FLAGS_RESPONSE, 'responseCode' => 200, 'curlErrno' => 0],
+        ]);
+        $this->client = new Client(
+            self::FAKE_API_KEY,
+            [
+                "debug" => true,
+                "maximum_backoff_duration" => 101,
+            ],
+            $this->http_client,
+            null
+        );
+
+        $response = $this->client->flags('user-id');
+
+        $this->assertTrue($response['featureFlags']['simpleFlag']);
+        $this->assertCount(2, $this->http_client->calls);
+        foreach ($this->http_client->calls as $call) {
+            $this->assertSame('/flags/?v=2', $call['path']);
+            $this->assertEquals(["timeout" => 3000, "shouldRetry" => false], $call['requestOptions']);
+        }
+    }
+
+    /**
+     * @dataProvider retryableFlagsStatusCodes
+     */
+    public function testFlagsRequestStopsAfterExhaustingHttp502And504Retries(int $statusCode): void
+    {
+        $this->http_client = new MockedHttpClient("app.posthog.com");
+        $this->http_client->setFlagsEndpointResponseQueue([
+            ['response' => [], 'responseCode' => $statusCode, 'curlErrno' => 0],
+            ['response' => [], 'responseCode' => $statusCode, 'curlErrno' => 0],
+            ['response' => [], 'responseCode' => $statusCode, 'curlErrno' => 0],
+            ['response' => MockedResponses::FLAGS_RESPONSE, 'responseCode' => 200, 'curlErrno' => 0],
+        ]);
+        $this->client = new Client(
+            self::FAKE_API_KEY,
+            [
+                "debug" => true,
+                "feature_flag_request_max_retries" => 2,
+                "maximum_backoff_duration" => 101,
+            ],
+            $this->http_client,
+            null
+        );
+
+        $this->assertSame([
+            'featureFlags' => [],
+            'featureFlagPayloads' => [],
+            'flags' => [],
+        ], $this->client->flags('user-id'));
+        $this->assertCount(3, $this->http_client->calls);
+        foreach ($this->http_client->calls as $call) {
+            $this->assertSame('/flags/?v=2', $call['path']);
+            $this->assertEquals(["timeout" => 3000, "shouldRetry" => false], $call['requestOptions']);
+        }
+    }
+
+    /**
+     * @dataProvider retryableFlagsStatusCodes
+     */
+    public function testFlagsRequestDoesNotRetryHttp502And504WhenConfiguredMaxRetriesIsZero(int $statusCode): void
+    {
+        $this->http_client = new MockedHttpClient("app.posthog.com");
+        $this->http_client->setFlagsEndpointResponseQueue([
+            ['response' => [], 'responseCode' => $statusCode, 'curlErrno' => 0],
+            ['response' => MockedResponses::FLAGS_RESPONSE, 'responseCode' => 200, 'curlErrno' => 0],
+        ]);
+        $this->client = new Client(
+            self::FAKE_API_KEY,
+            [
+                "debug" => true,
+                "feature_flag_request_max_retries" => 0,
+                "maximum_backoff_duration" => 101,
+            ],
+            $this->http_client,
+            null
+        );
+
+        $this->assertSame([
+            'featureFlags' => [],
+            'featureFlagPayloads' => [],
+            'flags' => [],
+        ], $this->client->flags('user-id'));
+        $this->assertCount(1, $this->http_client->calls);
+    }
+
     /**
      * @dataProvider decideResponseCases
      */