diff --git a/app/Rules/SafeWebhookUrl.php b/app/Rules/SafeWebhookUrl.php
index 0316da0bc..0c0787eae 100644
--- a/app/Rules/SafeWebhookUrl.php
+++ b/app/Rules/SafeWebhookUrl.php
@@ -111,11 +111,20 @@ class SafeWebhookUrl implements ValidationRule
             return $options;
         }
 
+        // libcurl keeps only the last CURLOPT_RESOLVE entry for a given
+        // host:port pair, so every resolved address must be pinned in a single
+        // comma-separated entry. Emitting one entry per address silently drops
+        // all but the last, which is an IPv6 address whenever the host has AAAA
+        // records -- and that fails instantly on hosts without IPv6 egress.
+        $addresses = implode(',', array_map(
+            fn (string $ip): string => filter_var($ip, FILTER_VALIDATE_IP, FILTER_FLAG_IPV6) ? '['.$ip.']' : $ip,
+            $target['ips'],
+        ));
+
         $options['curl'] = [
-            CURLOPT_RESOLVE => array_map(
-                fn (string $ip): string => sprintf('%s:%d:%s', $target['host'], $target['port'], filter_var($ip, FILTER_VALIDATE_IP, FILTER_FLAG_IPV6) ? '['.$ip.']' : $ip),
-                $target['ips'],
-            ),
+            CURLOPT_RESOLVE => [
+                sprintf('%s:%d:%s', $target['host'], $target['port'], $addresses),
+            ],
         ];
 
         return $options;
diff --git a/tests/Unit/SafeWebhookUrlTest.php b/tests/Unit/SafeWebhookUrlTest.php
index 84d1b33ff..5dc2d057e 100644
--- a/tests/Unit/SafeWebhookUrlTest.php
+++ b/tests/Unit/SafeWebhookUrlTest.php
@@ -219,10 +219,32 @@ it('builds HTTP client options that pin resolved DNS for the request', function
     expect($options['allow_redirects'])->toBeFalse();
 
     if (defined('CURLOPT_RESOLVE')) {
-        expect($options['curl'][CURLOPT_RESOLVE])->toContain('localhost:8080:127.0.0.1');
+        expect($options['curl'][CURLOPT_RESOLVE])->toContain('localhost:8080:127.0.0.1,[::1]');
     }
 });
 
+it('pins every resolved address in a single CURLOPT_RESOLVE entry', function () {
+    InstanceSettings::unguarded(fn () => InstanceSettings::query()->updateOrCreate(['id' => 0], [
+        'webhook_allowed_internal_hosts' => ['localhost'],
+        'webhook_allow_localhost' => true,
+    ]));
+
+    if (! defined('CURLOPT_RESOLVE')) {
+        expect(true)->toBeTrue();
+
+        return;
+    }
+
+    $entries = SafeWebhookUrl::httpClientOptions('http://localhost:8080/webhook')['curl'][CURLOPT_RESOLVE];
+
+    // localhost resolves to both 127.0.0.1 and ::1. libcurl overrides an
+    // existing host:port cache entry with each new one, so multiple entries
+    // would leave only [::1] pinned and break every request on hosts without
+    // IPv6 egress.
+    expect($entries)->toHaveCount(1)
+        ->and($entries[0])->toBe('localhost:8080:127.0.0.1,[::1]');
+});
+
 it('fails closed while building HTTP options when the send-time resolution is unsafe', function () {
     expect(fn () => SafeWebhookUrl::httpClientOptions('http://localhost:8080/webhook'))
         ->toThrow(RuntimeException::class, 'unsafe IP address');