diff --git a/src/Plugin.php b/src/Plugin.php
index eeb8a72..c1fad1e 100644
--- a/src/Plugin.php
+++ b/src/Plugin.php
@@ -29,6 +29,7 @@ use LIT\MCP\Integrations\WordPress\Schema\ContentSchema;
 use LIT\MCP\Integrations\WordPress\Schema\RegisteredMetaSource;
 use LIT\MCP\Integrations\WordPress\Schema\SampledMetaSource;
 use LIT\MCP\Integrations\WordPress\WordPressIntegration;
+use LIT\MCP\Server\DiscoveryCanonical;
 use LIT\MCP\Server\RequestContext;
 use LIT\MCP\Server\ServerRegistrar;
 use LIT\MCP\Server\VisibilityFilter;
@@ -57,6 +58,7 @@ final class Plugin
         $access->register();
         (new RequestContext())->register();
         (new VisibilityFilter())->register();
+        (new DiscoveryCanonical())->register();
 
         $limits = new Limits();
         $changeLog = new ChangeLog();
diff --git a/src/Server/DiscoveryCanonical.php b/src/Server/DiscoveryCanonical.php
new file mode 100644
index 0000000..13c9f0e
--- /dev/null
+++ b/src/Server/DiscoveryCanonical.php
@@ -0,0 +1,29 @@
+<?php
+
+declare(strict_types=1);
+
+namespace LIT\MCP\Server;
+
+/**
+ * Keeps WordPress' canonical redirect away from mcp-oauth's two discovery documents.
+ * With a pretty permalink structure ending in "/", WordPress 301-redirects
+ * /.well-known/oauth-protected-resource to a trailing-slash URL; the resource_metadata
+ * URL in the 401 header and RFC 8414/9728 clients use the exact path, so it must answer
+ * directly instead of relying on every client following redirects.
+ */
+final class DiscoveryCanonical
+{
+    private const PATH = '#/\.well-known/oauth-(?:protected-resource|authorization-server)/?$#D';
+
+    public function register(): void
+    {
+        add_filter('redirect_canonical', [$this, 'filter'], 10, 2);
+    }
+
+    public function filter(mixed $redirect, mixed $requested): mixed
+    {
+        $path = is_string($requested) ? (string) wp_parse_url($requested, PHP_URL_PATH) : '';
+
+        return preg_match(self::PATH, $path) === 1 ? false : $redirect;
+    }
+}
diff --git a/tests/Integration/mcp-smoke.sh b/tests/Integration/mcp-smoke.sh
index 84f24bc..9e80296 100644
--- a/tests/Integration/mcp-smoke.sh
+++ b/tests/Integration/mcp-smoke.sh
@@ -60,14 +60,16 @@ curl -s --max-time 20 -H "Host: $HOST" -H 'X-Forwarded-Proto: https' \
   || fail "authorization-server metadata missing CIMD flag"
 pass "RFC 8414 authorization-server metadata advertises CIMD"
 
-# ENVIRONMENT check (never fails): the real .well-known path, same Host/proto.
-WELLKNOWN=$(curl -s --max-time 20 -H "Host: $HOST" -H 'X-Forwarded-Proto: https' \
-  'http://localhost/.well-known/oauth-protected-resource')
-if echo "$WELLKNOWN" | grep -q '"resource"'; then
-  pass "/.well-known/ reachable"
-else
-  echo "WARN - /.well-known/ blocked by web server config (claude.ai discovery will fail; allow .well-known in nginx)"
-fi
+# The real .well-known path, same Host/proto, WITHOUT following redirects: clients use
+# the exact resource_metadata URL from the 401 header. Needs the web server to pass
+# /.well-known/ to WordPress (DDEV: .ddev/nginx/well-known.conf) and the plugin's
+# DiscoveryCanonical (no trailing-slash 301).
+for DOC in oauth-protected-resource oauth-authorization-server; do
+  CODE=$(curl -s --max-time 20 -o /dev/null -w '%{http_code}' -H "Host: $HOST" -H 'X-Forwarded-Proto: https' \
+    "http://localhost/.well-known/$DOC")
+  [ "$CODE" = "200" ] || fail "/.well-known/$DOC answered $CODE (web server blocks it or WordPress redirects)"
+done
+pass "/.well-known/ discovery documents answer directly (200, no redirect)"
 
 # 2. Unauthenticated request -> 401 with WWW-Authenticate
 UNAUTH=$(curl -s --max-time 20 -i -X POST "$ENDPOINT" -H 'Content-Type: application/json' -d '{"jsonrpc":"2.0","id":1,"method":"tools/list"}')
diff --git a/tests/Unit/Server/DiscoveryCanonicalTest.php b/tests/Unit/Server/DiscoveryCanonicalTest.php
new file mode 100644
index 0000000..a5b4d2a
--- /dev/null
+++ b/tests/Unit/Server/DiscoveryCanonicalTest.php
@@ -0,0 +1,46 @@
+<?php
+
+declare(strict_types=1);
+
+namespace LIT\MCP\Tests\Unit\Server;
+
+use Brain\Monkey\Functions;
+use LIT\MCP\Server\DiscoveryCanonical;
+use LIT\MCP\Tests\Unit\TestCase;
+
+final class DiscoveryCanonicalTest extends TestCase
+{
+    protected function setUp(): void
+    {
+        parent::setUp();
+        Functions\when('wp_parse_url')->alias('parse_url');
+    }
+
+    /** @return array<string, array{string}> */
+    public static function discoveryUrls(): array
+    {
+        return [
+            'protected resource' => ['https://example.test/.well-known/oauth-protected-resource'],
+            'authorization server' => ['https://example.test/.well-known/oauth-authorization-server'],
+            'subdirectory install' => ['https://example.test/wp/.well-known/oauth-protected-resource'],
+        ];
+    }
+
+    /** @dataProvider discoveryUrls */
+    public function testDiscoveryDocumentsAreNeverRedirected(string $requested): void
+    {
+        self::assertFalse((new DiscoveryCanonical())->filter($requested . '/', $requested));
+    }
+
+    public function testOtherRedirectsStayUntouched(): void
+    {
+        $filter = new DiscoveryCanonical();
+
+        $page = 'https://example.test/seite';
+        $acme = 'https://example.test/.well-known/acme-challenge/x';
+
+        self::assertSame($page . '/', $filter->filter($page . '/', $page));
+        self::assertSame($acme . '/', $filter->filter($acme . '/', $acme));
+        self::assertFalse($filter->filter(false, 'https://example.test/.well-known/oauth-authorization-server'));
+    }
+}