diff --git a/app/Auth/Oidc/OidcDiscoveryService.php b/app/Auth/Oidc/OidcDiscoveryService.php
index 0847afc9a7..eddddb219e 100644
--- a/app/Auth/Oidc/OidcDiscoveryService.php
+++ b/app/Auth/Oidc/OidcDiscoveryService.php
@@ -21,7 +21,7 @@ class OidcDiscoveryService
             $url = $issuerUrl.'/.well-known/openid-configuration';
 
             try {
-                $response = Http::timeout(5)->connectTimeout(3)->acceptJson()->get($url);
+                $response = Http::timeout(15)->acceptJson()->get($url);
             } catch (Throwable $e) {
                 throw new OidcDiscoveryException("Failed to fetch discovery document: {$e->getMessage()}", previous: $e);
             }
@@ -68,7 +68,7 @@ class OidcDiscoveryService
 
         return Cache::remember($cacheKey, 21600, function () use ($jwksUri): array {
             try {
-                $response = Http::timeout(5)->connectTimeout(3)->acceptJson()->get($jwksUri);
+                $response = Http::timeout(15)->acceptJson()->get($jwksUri);
             } catch (Throwable $e) {
                 throw new OidcJwksException("Failed to fetch JWKS: {$e->getMessage()}", previous: $e);
             }
diff --git a/app/Http/Controllers/Webhook/Github.php b/app/Http/Controllers/Webhook/Github.php
index e644a68c26..c69487031d 100644
--- a/app/Http/Controllers/Webhook/Github.php
+++ b/app/Http/Controllers/Webhook/Github.php
@@ -735,7 +735,6 @@ class Github extends Controller
         $data = Http::GitSource($api_url)->withBody(null)
             ->accept('application/vnd.github+json')
             ->timeout(10)
-            ->connectTimeout(5)
             ->post("$api_url/app-manifests/$code/conversions")
             ->throw()
             ->json();
@@ -841,7 +840,6 @@ class Github extends Controller
                 'Accept' => 'application/vnd.github+json',
             ])
                 ->timeout(10)
-                ->connectTimeout(5)
                 ->get("{$github_app->api_url}/app/installations/{$installation_id}");
         } catch (\Throwable $e) {
             return strip_tags(str_replace('<br>', ' ', $e->getMessage()));
diff --git a/app/Providers/AppServiceProvider.php b/app/Providers/AppServiceProvider.php
index 8130a5400d..674cf95914 100644
--- a/app/Providers/AppServiceProvider.php
+++ b/app/Providers/AppServiceProvider.php
@@ -9,6 +9,7 @@ use App\Models\PersonalAccessToken;
 use App\Models\Server;
 use App\Rules\SafeExternalUrl;
 use App\Support\AtomicFilesystem;
+use App\Support\RetryHttpConnectionFailures;
 use Illuminate\Database\Eloquent\Model;
 use Illuminate\Foundation\Console\ConfigCacheCommand;
 use Illuminate\Foundation\Console\RouteCacheCommand;
@@ -43,6 +44,7 @@ class AppServiceProvider extends ServiceProvider
         $this->configureModels();
         $this->configurePasswords();
         $this->configureSanctumModel();
+        $this->configureHttpClient();
         $this->configureGitHubHttp();
         $this->configureGitLabHttp();
         $this->configureOidcSocialite();
@@ -124,6 +126,12 @@ class AppServiceProvider extends ServiceProvider
         });
     }
 
+    private function configureHttpClient(): void
+    {
+        Http::globalOptions(['connect_timeout' => 10, 'timeout' => 30]);
+        Http::globalMiddleware(new RetryHttpConnectionFailures);
+    }
+
     private function configureGitHubHttp(): void
     {
         Http::macro('GitSource', function (string $url) {
diff --git a/app/Services/CloudflareHttp.php b/app/Services/CloudflareHttp.php
deleted file mode 100644
index 7e301b37fe..0000000000
--- a/app/Services/CloudflareHttp.php
+++ /dev/null
@@ -1,24 +0,0 @@
-<?php
-
-namespace App\Services;
-
-use Illuminate\Http\Client\ConnectionException;
-use Illuminate\Http\Client\PendingRequest;
-use Illuminate\Support\Facades\Http;
-
-class CloudflareHttp
-{
-    /**
-     * The connect timeout is longer than the 5 second DNS resolver retry, so one lost DNS query does not fail the request.
-     * Only idempotent requests are retried after a connection failure; a POST can reach Cloudflare before the timeout.
-     */
-    public static function client(string $token): PendingRequest
-    {
-        return Http::withToken($token)
-            ->acceptJson()
-            ->connectTimeout(10)
-            ->timeout(20)
-            ->retry(2, 500, fn ($exception, $request, ?string $method) => $exception instanceof ConnectionException
-                && in_array($method, ['GET', 'PUT', 'DELETE'], true), throw: false);
-    }
-}
diff --git a/app/Services/CloudflareTokenValidator.php b/app/Services/CloudflareTokenValidator.php
index baa622f14b..265268ccb0 100644
--- a/app/Services/CloudflareTokenValidator.php
+++ b/app/Services/CloudflareTokenValidator.php
@@ -2,11 +2,13 @@
 
 namespace App\Services;
 
+use Illuminate\Support\Facades\Http;
+
 class CloudflareTokenValidator
 {
     public function validate(string $token, array $capabilities): bool
     {
-        $client = CloudflareHttp::client($token);
+        $client = Http::withToken($token)->acceptJson();
         $verification = $client->get('https://api.cloudflare.com/client/v4/user/tokens/verify');
 
         if (! $verification->successful() || $verification->json('result.status') !== 'active') {
diff --git a/app/Services/CloudflareTunnelService.php b/app/Services/CloudflareTunnelService.php
index c55785e59d..ac25a3b0eb 100644
--- a/app/Services/CloudflareTunnelService.php
+++ b/app/Services/CloudflareTunnelService.php
@@ -14,6 +14,7 @@ use App\Services\Dns\ManagedDnsRecordCleanup;
 use Illuminate\Contracts\Cache\LockTimeoutException;
 use Illuminate\Http\Client\PendingRequest;
 use Illuminate\Http\Client\Response;
+use Illuminate\Support\Facades\Http;
 use Illuminate\Support\Sleep;
 use RuntimeException;
 use Spatie\Activitylog\Models\Activity;
@@ -282,6 +283,6 @@ class CloudflareTunnelService
 
     private function client(IntegrationToken $token): PendingRequest
     {
-        return CloudflareHttp::client($token->token);
+        return Http::withToken($token->token)->acceptJson();
     }
 }
diff --git a/app/Services/Dns/CloudflareDnsProvider.php b/app/Services/Dns/CloudflareDnsProvider.php
index e8d9c0ae71..614ab066dd 100644
--- a/app/Services/Dns/CloudflareDnsProvider.php
+++ b/app/Services/Dns/CloudflareDnsProvider.php
@@ -11,13 +11,13 @@ use App\Models\IntegrationToken;
 use App\Models\ManagedDnsRecord;
 use App\Models\Server;
 use App\Models\ServiceApplication;
-use App\Services\CloudflareHttp;
 use App\Support\DnsRecordHints;
 use Illuminate\Contracts\Cache\LockTimeoutException;
 use Illuminate\Database\Eloquent\Model;
 use Illuminate\Http\Client\PendingRequest;
 use Illuminate\Support\Collection;
 use Illuminate\Support\Facades\DB;
+use Illuminate\Support\Facades\Http;
 use RuntimeException;
 use Throwable;
 
@@ -512,6 +512,6 @@ class CloudflareDnsProvider
 
     private function client(IntegrationToken $token): PendingRequest
     {
-        return CloudflareHttp::client($token->token);
+        return Http::withToken($token->token)->acceptJson();
     }
 }
diff --git a/app/Services/DopplerService.php b/app/Services/DopplerService.php
index 2513a4f7d8..b9cf24650e 100644
--- a/app/Services/DopplerService.php
+++ b/app/Services/DopplerService.php
@@ -50,8 +50,6 @@ class DopplerService
     private function client(): PendingRequest
     {
         return Http::withToken($this->token)
-            ->acceptJson()
-            ->connectTimeout(5)
-            ->timeout(10);
+            ->acceptJson();
     }
 }
diff --git a/app/Support/RetryHttpConnectionFailures.php b/app/Support/RetryHttpConnectionFailures.php
new file mode 100644
index 0000000000..1ab42313a0
--- /dev/null
+++ b/app/Support/RetryHttpConnectionFailures.php
@@ -0,0 +1,47 @@
+<?php
+
+namespace App\Support;
+
+use GuzzleHttp\Exception\ConnectException;
+use GuzzleHttp\Promise\Create;
+use GuzzleHttp\Promise\PromiseInterface;
+use Illuminate\Support\Sleep;
+use Psr\Http\Message\RequestInterface;
+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.
+ */
+class RetryHttpConnectionFailures
+{
+    private const array RETRIED_METHODS = ['GET', 'HEAD', 'OPTIONS', 'PUT', 'DELETE'];
+
+    public function __invoke(callable $handler): callable
+    {
+        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)) {
+                    return Create::rejectionFor($exception);
+                }
+
+                Sleep::usleep(500_000);
+
+                return $this->send($handler, $request, $options);
+            });
+        };
+    }
+
+    /**
+     * The cURL handler rejects the promise on a connection failure, but other handlers (such as Http::fake()) throw.
+     */
+    private function send(callable $handler, RequestInterface $request, array $options): PromiseInterface
+    {
+        try {
+            return Create::promiseFor($handler($request, $options));
+        } catch (ConnectException $exception) {
+            return Create::rejectionFor($exception);
+        }
+    }
+}
diff --git a/tests/Feature/DnsProviderManagementTest.php b/tests/Feature/DnsProviderManagementTest.php
index b3a6d8a382..2d5a75858d 100644
--- a/tests/Feature/DnsProviderManagementTest.php
+++ b/tests/Feature/DnsProviderManagementTest.php
@@ -945,7 +945,7 @@ test('cloudflare dns reads are retried after a connection failure but record cre
     expect(fn () => app(CloudflareDnsProvider::class)->createRecord($zone, 'app.example.com', '203.0.113.10'))
         ->toThrow(ConnectionException::class);
 
-    Http::assertSentCount(3);
-    Http::assertSent(fn ($request) => $request->method() === 'POST');
+    Http::assertSequencesAreEmpty();
+    expect(collect(Http::recorded())->filter(fn (array $pair) => $pair[0]->method() === 'POST'))->toHaveCount(1);
     expect(ManagedDnsRecord::query()->count())->toBe(0);
 });
diff --git a/tests/Feature/HttpConnectionRetryTest.php b/tests/Feature/HttpConnectionRetryTest.php
new file mode 100644
index 0000000000..58543a1387
--- /dev/null
+++ b/tests/Feature/HttpConnectionRetryTest.php
@@ -0,0 +1,40 @@
+<?php
+
+use Illuminate\Http\Client\ConnectionException;
+use Illuminate\Support\Facades\Http;
+use Illuminate\Support\Sleep;
+
+beforeEach(function () {
+    Sleep::fake();
+    $this->attempts = 0;
+});
+
+function fakeConnectionFailures(int $failures): void
+{
+    Http::fake(function () use ($failures) {
+        test()->attempts++;
+
+        return test()->attempts <= $failures ? Http::failedConnection() : Http::response(['ok' => true]);
+    });
+}
+
+test('a read request is retried once after a connection failure', function () {
+    fakeConnectionFailures(1);
+
+    expect(Http::get('https://api.example.com/items')->json('ok'))->toBeTrue()
+        ->and($this->attempts)->toBe(2);
+});
+
+test('a read request fails when the retry also has a connection failure', function () {
+    fakeConnectionFailures(2);
+
+    expect(fn () => Http::delete('https://api.example.com/items/1'))->toThrow(ConnectionException::class)
+        ->and($this->attempts)->toBe(2);
+});
+
+test('a post request is not retried because the server can have received it', function () {
+    fakeConnectionFailures(1);
+
+    expect(fn () => Http::post('https://api.example.com/items'))->toThrow(ConnectionException::class)
+        ->and($this->attempts)->toBe(1);
+});