diff --git a/lib/classes/router/middleware/moodle_bootstrap_middleware.php b/lib/classes/router/middleware/moodle_bootstrap_middleware.php
index 004cfc5f784..c6872d252bb 100644
--- a/lib/classes/router/middleware/moodle_bootstrap_middleware.php
+++ b/lib/classes/router/middleware/moodle_bootstrap_middleware.php
@@ -33,7 +33,7 @@ use Psr\Http\Server\RequestHandlerInterface;
 class moodle_bootstrap_middleware implements MiddlewareInterface {
     #[\Override]
     public function process(ServerRequestInterface $request, RequestHandlerInterface $handler): ResponseInterface {
-        global $PAGE;
+        global $CFG, $PAGE;
 
         if (str_contains($request->getUri(), route_loader_interface::ROUTE_GROUP_API)) {
             // @codeCoverageIgnoreStart
@@ -58,7 +58,52 @@ class moodle_bootstrap_middleware implements MiddlewareInterface {
             $this->load_full_moodle();
         }
 
-        $PAGE->set_url((string) $request->getUri());
+        // Set the URL for the page.
+        // Normally in Moodle this is a largely hard-coded value with only the query string changing dynamically in the page.
+        // However, in this instance, we are generating the URL dynamically because we are the request terminator
+        // for a large number of requests at different endpoints.
+
+        // In basic cases this will just work, but there are some edge cases to consider - specficially were the site
+        // is behind a reverse proxy and/or an SSL terminator.
+        // In these cases the URL we generate from the ServerRequestInterface may be the _terminated_ URL,
+        // and not the URL that was requested by the client.
+
+        // We need to generate the URL that the client requested, not the URL that the server received.
+        $url = $request->getUri();
+
+        if (!empty($CFG->reverseproxy)) {
+            // This site is behind a reverse proxy. The requested URI may have a different:
+            // - scheme
+            // - host
+            // - port
+            // to the URL that the client requested.
+
+            $url = $url
+                // Start by setting the scheme and host to the wwwroot.
+                ->withScheme(parse_url($CFG->wwwroot, PHP_URL_SCHEME))
+                ->withHost(parse_url($CFG->wwwroot, PHP_URL_HOST))
+
+                // Update the URL to match the port of the wwwroot.
+                // While it is highly unlikely that a wwwroot includes an explicit port, we should still handle it.
+                ->withPort(parse_url($CFG->wwwroot, PHP_URL_PORT));
+
+        }
+
+        if (!empty($CFG->sslproxy)) {
+            // This site is behind an ssl terminating proxy. The requested URI may have a different:
+            // - scheme
+            // - port
+            // to the URL that the client requested.
+            $url = $url
+                // The wwwroot must use the https scheme, but the terminating request may have been received using http.
+                ->withScheme('https')
+
+                // Update the URL to match the port of the wwwroot.
+                // While it is highly unlikely that a wwwroot includes an explicit port, we should still handle it.
+                ->withPort(parse_url($CFG->wwwroot, PHP_URL_PORT));
+        }
+
+        $PAGE->set_url((string) $url);
 
         return $handler->handle($request);
     }
diff --git a/lib/tests/router/middleware/moodle_bootstrap_middleware_test.php b/lib/tests/router/middleware/moodle_bootstrap_middleware_test.php
index 078a5a295ba..323a3b9e911 100644
--- a/lib/tests/router/middleware/moodle_bootstrap_middleware_test.php
+++ b/lib/tests/router/middleware/moodle_bootstrap_middleware_test.php
@@ -17,8 +17,10 @@
 namespace core\router\middleware;
 
 use core\di;
+use core\url;
 use core\tests\route_testcase;
 use GuzzleHttp\Psr7\ServerRequest;
+use Slim\Exception\HttpNotFoundException;
 
 /**
  * Tests for the Moodle Bootstrap middleware.
@@ -30,21 +32,198 @@ use GuzzleHttp\Psr7\ServerRequest;
  * @covers \core\router\middleware\moodle_bootstrap_middleware
  */
 final class moodle_bootstrap_middleware_test extends route_testcase {
-    public function test_set_page_to_uri(): void {
-        global $PAGE;
+    /**
+     * Test setting of the page URI based on the request URI.
+     *
+     * @dataProvider page_url_provider
+     *
+     * @param string $pattern The pattern to register with the app.
+     * @param string $basepath The basepath of the wwwroot.
+     * @param string $uri The URI to test.
+     * @param array $cfg The configuration to use.
+     * @param string|false $expected The expected page URI, or false if no page URI is expected.
+     */
+    public function test_set_page_to_uri(
+        string $pattern,
+        string $basepath,
+        string $uri,
+        array $cfg,
+        string|false $expected
+    ): void {
+        global $CFG, $PAGE;
+
+        $this->resetAfterTest();
+
+        foreach ($cfg as $key => $value) {
+            $CFG->{$key} = $value;
+        }
+
         $app = $this->get_simple_app();
+        $app->setBasePath($basepath);
         $app->add(di::get(moodle_bootstrap_middleware::class));
         $app->addRoutingMiddleware();
 
-        $app->map(['GET'], '/example', function ($request, $response) {
-            return $response;
-        });
+        $app->map(
+            methods: ['GET'],
+            pattern: $pattern,
+            callable: fn ($request, $response) => $response,
+        );
 
         // Handle the request.
-        $request = new ServerRequest('GET', '/example');
-        $app->handle($request);
+        $request = new ServerRequest('GET', $uri);
 
-        $expect = new \moodle_url('/example');
-        $this->assertEquals($expect->out(), $PAGE->url->out());
+        if ($expected) {
+            $app->handle($request);
+            $expect = new url($expected);
+            $this->assertEquals($expect->out(), $PAGE->url->out());
+        } else {
+            $this->expectException(HttpNotFoundException::class);
+            $app->handle($request);
+        }
+    }
+
+    /**
+     * Data provider for test_set_page_to_uri.
+     *
+     * @return array
+     */
+    public static function page_url_provider(): array {
+        return [
+            'A basic URI' => [
+                'pattern' => '/example',
+                'basepath' => '',
+                'uri' => '/example',
+                'cfg' => [],
+                'expected' => '/example',
+            ],
+            'A basic URI including wwwroot' => [
+                'pattern' => '/example',
+                'basepath' => '/example/path',
+                'uri' => "https://example.com/example/path/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/example/path',
+                ],
+                'expected' => '/example',
+            ],
+            'A basic URI with query parameters' => [
+                'pattern' => '/example',
+                'basepath' => '',
+                'uri' => "https://example.com/example?foo=bar&baz=qux",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com',
+                ],
+                'expected' => "https://example.com/example?foo=bar&baz=qux",
+            ],
+            'A request behind a terminating SSL proxy' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://example.com:443/moodle/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/moodle',
+                    'sslproxy' => true,
+                ],
+                'expected' => 'https://example.com/moodle/example',
+            ],
+            'A request behind a terminating SSL proxy with query parameters' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://example.com:443/moodle/example?foo=bar&baz=qux",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/moodle',
+                    'sslproxy' => true,
+                ],
+                'expected' => 'https://example.com/moodle/example?foo=bar&baz=qux',
+            ],
+            'A request behind a terminating SSL proxy and random port' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://example.com:1024/moodle/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/moodle',
+                    'sslproxy' => true,
+                ],
+                'expected' => 'https://example.com/moodle/example',
+            ],
+            'A request behind a terminating SSL proxy and random port where the wwwroot has an explicit port' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://example.com:1024/moodle/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com:8443/moodle',
+                    'sslproxy' => true,
+                ],
+                'expected' => 'https://example.com:8443/moodle/example',
+            ],
+            'A request behind a terminating SSL proxy where the wwwroot has an explicity port and query parameters' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://example.com:1024/moodle/example?foo=bar&baz=qux",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com:8443/moodle',
+                    'sslproxy' => true,
+                ],
+                'expected' => 'https://example.com:8443/moodle/example?foo=bar&baz=qux',
+            ],
+            'A request behind a SSL proxy proxy with different path is invalid' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://example.com:443/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/moodle',
+                    'sslproxy' => true,
+                ],
+                'expected' => false,
+            ],
+            'A request behind a reverse proxy' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://172.30.10.101:443/moodle/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/moodle',
+                    'reverseproxy' => true,
+                ],
+                'expected' => 'https://example.com/moodle/example',
+            ],
+            'A request behind a reverse proxy with query params' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://172.30.10.101:443/moodle/example?foo=bar&baz=qux",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/moodle',
+                    'reverseproxy' => true,
+                ],
+                'expected' => 'https://example.com/moodle/example?foo=bar&baz=qux',
+            ],
+            'A request behind a reverse proxy with different path is invalid' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://172.30.10.101:443/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com/moodle',
+                    'reverseproxy' => true,
+                ],
+                'expected' => false,
+            ],
+            'A request behind a reverse proxy where the wwwroot has an explicit port' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://172.30.10.101:443/moodle/example",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com:8443/moodle',
+                    'reverseproxy' => true,
+                ],
+                'expected' => 'https://example.com:8443/moodle/example',
+            ],
+            'A request behind a reverse proxy where the wwwroot has an explicit port and parameters' => [
+                'pattern' => '/example',
+                'basepath' => '/moodle',
+                'uri' => "http://172.30.10.101:443/moodle/example?foo=bar&baz=qux",
+                'cfg' => [
+                    'wwwroot' => 'https://example.com:8443/moodle',
+                    'reverseproxy' => true,
+                ],
+                'expected' => 'https://example.com:8443/moodle/example?foo=bar&baz=qux',
+            ],
+        ];
     }
 }