diff --git a/CHANGELOG-WIP.md b/CHANGELOG-WIP.md
index 3cdcdaa28c0..871413917e9 100644
--- a/CHANGELOG-WIP.md
+++ b/CHANGELOG-WIP.md
@@ -70,6 +70,7 @@
 - It’s now possible to reference custom field handles in element queries’ `where` params. ([#16318](https://github.com/craftcms/cms/pull/16318))
 - Number fields’ scalar values now return an integer if Decimals is set to `0`, and a number formatted with the correct decimal points when using MySQL. ([16369](https://github.com/craftcms/cms/issues/16369))
 - Added support for specifying the current site via an `X-Craft-Site` header set to a site ID or handle. ([#16367](https://github.com/craftcms/cms/pull/16367))
+- Added support for defining redirects from `config/redirects.php`. ([#16355](https://github.com/craftcms/cms/pull/16355))
 - Deprecated the `ucfirst` Twig filter. `capitalize` should be used instead.
 
 ### Extensibility
@@ -93,6 +94,7 @@
 - Added `craft\elements\db\ElementQueryInterface::getFieldLayouts()`.
 - Added `craft\elements\db\NestedElementQueryTrait::fieldLayouts()`.
 - Added `craft\events\DefineAltActionsEvent`.
+- Added `craft\events\RedirectEvent`. ([#16355](https://github.com/craftcms/cms/pull/16355))
 - Added `craft\fieldlayoutelements\BaseField::actionMenuItems()`.
 - Added `craft\fieldlayoutelements\BaseField::isCrossSiteCopyable()`.
 - Added `craft\fields\BaseRelationField::gqlFieldArguments()`.
@@ -122,6 +124,9 @@
 - Added `craft\models\MailSettings::$siteOverrides`.
 - Added `craft\services\Elements::canSaveCanonical()`.
 - Added `craft\services\Gql::getFieldLayoutArguments()`.
+- Added `craft\web\ErrorHandler::EVENT_BEFORE_REDIRECT`. ([#16355](https://github.com/craftcms/cms/pull/16355))
+- Added `craft\web\RedirectRule`. ([#16355](https://github.com/craftcms/cms/pull/16355))
+- Added `craft\web\UrlRule::regexTokens()`.
 - Added `craft\web\User::getImpersonator()`.
 - Added `craft\web\User::getImpersonatorId()`.
 - Added `craft\web\User::setImpersonatorId()`.
@@ -137,6 +142,7 @@
 - `craft\models\Site` now implements `craft\base\Chippable`.
 - `craft\services\Revisions::createRevision()` no longer creates the revision if an `EVENT_BEFORE_CREATE_REVISION` event handler sets `$event->handled` to `true` and at least one revision already exists for the element. ([#16260](https://github.com/craftcms/cms/discussions/16260))
 - Elements’ `defineCardAttributes()` methods can now return a `placeholder` value set to a callable.
+- Deprecated `craft\controllers\RedirectController`. ([#16355](https://github.com/craftcms/cms/pull/16355))
 - Deprecated `craft\elements\User::EVENT_REGISTER_USER_ACTIONS`.
 - Deprecated `craft\elements\User::IMPERSONATE_KEY`. `craft\web\User::getImpersonatorId()` should be used instead.
 - Deprecated `craft\fields\Color::$presets`. ([#16249](https://github.com/craftcms/cms/pull/16249))
diff --git a/src/controllers/RedirectController.php b/src/controllers/RedirectController.php
index bfcf667f3d9..f790c377f58 100644
--- a/src/controllers/RedirectController.php
+++ b/src/controllers/RedirectController.php
@@ -17,6 +17,7 @@
  *
  * @author Pixel & Tonic, Inc. <support@pixelandtonic.com>
  * @since 3.5.13
+ * @deprecated in 5.6.0. `config/redirects.php` should be used instead.
  */
 class RedirectController extends Controller
 {
diff --git a/src/events/RedirectEvent.php b/src/events/RedirectEvent.php
new file mode 100644
index 00000000000..3e9912fe495
--- /dev/null
+++ b/src/events/RedirectEvent.php
@@ -0,0 +1,22 @@
+<?php
+/**
+ * @link https://craftcms.com/
+ * @copyright Copyright (c) Pixel & Tonic, Inc.
+ * @license https://craftcms.github.io/license/
+ */
+
+namespace craft\events;
+
+use craft\base\Event;
+use craft\web\RedirectRule;
+
+/**
+ * RedirectEvent class.
+ *
+ * @author Pixel & Tonic, Inc. <support@pixelandtonic.com>
+ * @since 5.6.0
+ */
+class RedirectEvent extends Event
+{
+    public RedirectRule $rule;
+}
diff --git a/src/web/ErrorHandler.php b/src/web/ErrorHandler.php
index 16b80b11c54..a8bb386d218 100644
--- a/src/web/ErrorHandler.php
+++ b/src/web/ErrorHandler.php
@@ -9,6 +9,7 @@
 
 use Craft;
 use craft\events\ExceptionEvent;
+use craft\events\RedirectEvent;
 use craft\helpers\App;
 use craft\helpers\Json;
 use craft\helpers\Template;
@@ -38,6 +39,12 @@ class ErrorHandler extends \yii\web\ErrorHandler
      */
     public const EVENT_BEFORE_HANDLE_EXCEPTION = 'beforeHandleException';
 
+    /**
+     * @event RedirectEvent The event that is triggered before a 404 redirect.
+     * @since 5.6.0
+     */
+    public const EVENT_BEFORE_REDIRECT = 'beforeRedirect';
+
     /**
      * @inheritdoc
      */
@@ -57,6 +64,36 @@ public function handleException($exception): void
 
         // 404?
         if ($exception instanceof HttpException && $exception->statusCode === 404) {
+            $redirectRules = Craft::$app->getConfig()->getConfigFromFile('redirects');
+            if ($redirectRules) {
+                foreach ($redirectRules as $from => $rule) {
+                    if (!$rule instanceof RedirectRule) {
+                        $config = is_string($rule) ? ['to' => $rule] : $rule;
+                        $rule = Craft::createObject([
+                            'class' => RedirectRule::class,
+                            'from' => $from,
+                            ...$config,
+                        ]);
+                    }
+
+                    $url = $rule->getMatch();
+
+                    if ($url === null) {
+                        continue;
+                    }
+
+                    if ($this->hasEventHandlers(self::EVENT_BEFORE_REDIRECT)) {
+                        $this->trigger(self::EVENT_BEFORE_REDIRECT, new RedirectEvent([
+                            'rule' => $rule,
+                        ]));
+                        ;
+                    }
+
+                    Craft::$app->getResponse()->redirect($url, $rule->statusCode);
+                    Craft::$app->end();
+                }
+            }
+
             $request = Craft::$app->getRequest();
             if ($request->getIsSiteRequest() && $request->getPathInfo() === 'wp-admin') {
                 $exception->statusCode = 418;
diff --git a/src/web/RedirectRule.php b/src/web/RedirectRule.php
new file mode 100644
index 00000000000..efc359a0793
--- /dev/null
+++ b/src/web/RedirectRule.php
@@ -0,0 +1,119 @@
+<?php
+/**
+ * @link https://craftcms.com/
+ * @copyright Copyright (c) Pixel & Tonic, Inc.
+ * @license https://craftcms.github.io/license/
+ */
+
+namespace craft\web;
+
+use Closure;
+use Craft;
+use Illuminate\Support\Collection;
+use League\Uri\Http;
+use yii\base\Component;
+
+/**
+ * Class RedirectRule
+ *
+ * @author Pixel & Tonic, Inc. <support@pixelandtonic.com>
+ * @since 5.6.0
+ */
+class RedirectRule extends Component
+{
+    /**
+     * @event \yii\base\Event The event that is triggered before redirecting the request.
+     */
+    public const EVENT_BEFORE_REDIRECT = 'beforeRedirect';
+
+    public string $to;
+    public string $from;
+    public int $statusCode = 302;
+    public bool $caseSensitive = false;
+    private Closure $_match;
+    private array $regexTokens = [];
+
+    public function __invoke(): void
+    {
+        $url = $this->getMatch();
+
+        if ($url === null) {
+            return;
+        }
+
+        if ($this->hasEventHandlers(self::EVENT_BEFORE_REDIRECT)) {
+            $this->trigger(self::EVENT_BEFORE_REDIRECT);
+        }
+
+        Craft::$app->getResponse()->redirect($url, $this->statusCode);
+        Craft::$app->end();
+    }
+
+    public function getMatch(): ?string
+    {
+        if (isset($this->_match)) {
+            return ($this->_match)(Http::new(Craft::$app->getRequest()->getAbsoluteUrl()));
+        }
+
+        $subject = Craft::$app->getRequest()->getFullPath();
+
+        if (str_contains($this->from, '<')) {
+            if (preg_match(
+                $this->toRegexPattern($this->from),
+                $subject,
+                $matches,
+            )) {
+                return $this->replaceParams($this->to, $matches);
+            }
+
+            return null;
+        }
+
+        if ($this->caseSensitive) {
+            return strcmp($this->from, $subject) === 0 ? $this->to : null;
+        }
+
+        return strcasecmp($this->from, $subject) === 0 ? $this->to : null;
+    }
+
+    public function setMatch(callable $match): void
+    {
+        $this->_match = $match;
+    }
+
+    private function replaceParams(string $value, array $params): string
+    {
+        $params = Collection::make($params)
+            ->mapWithKeys(fn($item, $key) => ["<$key>" => $item]);
+
+        return strtr($value, $params->all());
+    }
+
+    private function toRegexPattern(string $from): string
+    {
+        // Tokenize the patterns first, so we only escape regex chars outside of patterns
+        $tokenizedPattern = preg_replace_callback('/<([\w._-]+):?([^>]+)?>/', function($match) {
+            $name = $match[1];
+            $pattern = strtr($match[2] ?? '[^\/]+', UrlRule::regexTokens());
+            $token = "<$name>";
+            $this->regexTokens[$token] = "(?P<$name>$pattern)";
+
+            return $token;
+        }, $from);
+
+        $replacements = array_merge($this->regexTokens, [
+            '.' => '\\.',
+            '*' => '\\*',
+            '$' => '\\$',
+            '[' => '\\[',
+            ']' => '\\]',
+            '(' => '\\(',
+            ')' => '\\)',
+        ]);
+
+        $pattern = strtr($tokenizedPattern, $replacements);
+        $flags = $this->caseSensitive ? 'u' : 'iu';
+
+        return "`^{$pattern}$`{$flags}";
+    }
+}
diff --git a/src/web/UrlRule.php b/src/web/UrlRule.php
index f5797d83d22..648a91a3659 100644
--- a/src/web/UrlRule.php
+++ b/src/web/UrlRule.php
@@ -10,6 +10,7 @@
 use Craft;
 use craft\helpers\ArrayHelper;
 use craft\helpers\StringHelper;
+use craft\validators\HandleValidator;
 
 /**
  * @inheritdoc
@@ -18,6 +19,28 @@
  */
 class UrlRule extends \yii\web\UrlRule
 {
+    /**
+     * Returns an array of regex tokens supported by URL rules.
+     *
+     * @return array
+     * @since 5.6.0
+     */
+    public static function regexTokens(): array
+    {
+        $slugChars = ['.', '_', '-'];
+        $slugWordSeparator = Craft::$app->getConfig()->getGeneral()->slugWordSeparator;
+        if ($slugWordSeparator !== '/' && !in_array($slugWordSeparator, $slugChars, true)) {
+            $slugChars[] = $slugWordSeparator;
+        }
+
+        return [
+            '{handle}' => sprintf('(?:%s)', HandleValidator::$handlePattern),
+            // Reference: http://www.regular-expressions.info/unicode.html
+            '{slug}' => sprintf('(?:[\p{L}\p{N}\p{M}%s]+)', preg_quote(implode($slugChars), '/')),
+            '{uid}' => sprintf('(?:%s)', StringHelper::UUID_PATTERN),
+        ];
+    }
+
     /**
      * @var array Pattern tokens that will be swapped out at runtime.
      */
@@ -50,19 +73,7 @@ public function __construct(array $config = [])
         if (isset($config['pattern'])) {
             // Swap out any regex tokens in the pattern
             if (!isset(self::$_regexTokens)) {
-                $slugChars = ['.', '_', '-'];
-                $slugWordSeparator = Craft::$app->getConfig()->getGeneral()->slugWordSeparator;
-
-                if ($slugWordSeparator !== '/' && !in_array($slugWordSeparator, $slugChars, true)) {
-                    $slugChars[] = $slugWordSeparator;
-                }
-
-                // Reference: http://www.regular-expressions.info/unicode.html
-                self::$_regexTokens = [
-                    '{handle}' => '(?:[a-zA-Z][a-zA-Z0-9_]*)',
-                    '{slug}' => '(?:[\p{L}\p{N}\p{M}' . preg_quote(implode($slugChars), '/') . ']+)',
-                    '{uid}' => StringHelper::UUID_PATTERN,
-                ];
+                self::$_regexTokens = static::regexTokens();
             }
 
             $config['pattern'] = strtr($config['pattern'], self::$_regexTokens);
diff --git a/tests/unit/web/RedirectRuleTest.php b/tests/unit/web/RedirectRuleTest.php
new file mode 100644
index 00000000000..6b220417bb5
--- /dev/null
+++ b/tests/unit/web/RedirectRuleTest.php
@@ -0,0 +1,144 @@
+<?php
+/**
+ * @link https://craftcms.com/
+ * @copyright Copyright (c) Pixel & Tonic, Inc.
+ * @license https://craftcms.github.io/license/
+ */
+
+namespace crafttests\unit\web;
+
+use craft\helpers\UrlHelper;
+use craft\test\TestCase;
+use craft\web\RedirectRule;
+use Psr\Http\Message\UriInterface;
+use UnitTester;
+
+/**
+ * Unit tests for RedirectRuleTest
+ *
+ * @author Pixel & Tonic, Inc. <support@pixelandtonic.com>
+ * @since 5.6.0
+ */
+class RedirectRuleTest extends TestCase
+{
+    /**
+     * @var UnitTester
+     */
+    protected UnitTester $tester;
+
+    /**
+     * @dataProvider getMatchDataProvider
+     * @param string|null $expected
+     * @param array $config
+     */
+    public function testGetMatch(?string $expected, string $path, ?string $url, array $config): void
+    {
+        $this->tester->mockCraftMethods('request', [
+            'getFullPath' => $path,
+            'getAbsoluteUrl' => $url,
+        ]);
+        $rule = new RedirectRule($config);
+        $this->assertSame($expected, $rule->getMatch());
+    }
+
+    public static function getMatchDataProvider(): array
+    {
+        return [
+            // Path match (case-insensitive by default)
+            [
+                null,
+                'nope',
+                UrlHelper::url('nope'),
+                [
+                    'from' => 'redirect/from',
+                    'to' => 'redirect/to',
+                ],
+            ],
+            [
+                'redirect/to',
+                'redirect/from',
+                UrlHelper::url('redirect/from'),
+                [
+                    'from' => 'redirect/from',
+                    'to' => 'redirect/to',
+                ],
+            ],
+            [
+                'redirect/to',
+                'redirect/from/$special.chars',
+                UrlHelper::url('redirect/from/$special.chars'),
+                [
+                    'from' => 'redirect/from/$special.chars',
+                    'to' => 'redirect/to',
+                ],
+            ],
+
+            // Path match with Yii URL Rule named parameters
+            // https://www.yiiframework.com/doc/guide/2.0/en/runtime-routing#named-parameters
+            [
+                'redirect/to/abc123',
+                'redirect/from/foo/abc123',
+                UrlHelper::url('redirect/from/foo/abc123'),
+                [
+                    'from' => 'redirect/from/foo/<bar:{handle}>',
+                    'to' => 'redirect/to/<bar>',
+                ],
+            ],
+            [
+                'redirect/to/abc-123',
+                'redirect/from/foo/abc-123',
+                UrlHelper::url('redirect/from/foo/abc-123'),
+                [
+                    'from' => 'redirect/from/foo/<bar:{slug}>',
+                    'to' => 'redirect/to/<bar>',
+                ],
+            ],
+            [
+                'redirect/to/55a89943-19a6-4f5e-8db7-8950f7f66e98',
+                'redirect/from/foo/55a89943-19a6-4f5e-8db7-8950f7f66e98',
+                UrlHelper::url('redirect/from/foo/55a89943-19a6-4f5e-8db7-8950f7f66e98'),
+                [
+                    'from' => 'redirect/from/foo/<bar:{uid}>',
+                    'to' => 'redirect/to/<bar>',
+                ],
+            ],
+
+            // Path match (case-sensitive)
+            [
+                'https://redirect.to/2025/01',
+                'redirect/FROM/2025/01',
+                UrlHelper::url('redirect/FROM/2025/01'),
+                [
+                    'from' => 'redirect/FROM/<year:\d{4}>/<month>',
+                    'to' => 'https://redirect.to/<year>/<month>',
+                    'caseSensitive' => true,
+                ],
+            ],
+            [
+                null,
+                'redirect/from/2025/01',
+                UrlHelper::url('redirect/from/2025/01'),
+                [
+                    'from' => 'redirect/FROM/<year:\d{4}>/<month>',
+                    'to' => 'https://redirect.to/<year>/<month>',
+                    'caseSensitive' => true,
+                ],
+            ],
+
+            // Custom match callback
+            [
+                'redirect/to/abc123',
+                'redirect/from',
+                UrlHelper::url('redirect/from', ['bar' => 'abc123']),
+                [
+                    'match' => function(UriInterface $url): ?string {
+                        parse_str($url->getQuery(), $params);
+                        return isset($params['bar'])
+                            ? sprintf('redirect/to/%s', $params['bar'])
+                            : null;
+                    },
+                ],
+            ],
+        ];
+    }
+}