diff --git a/lib/moodlelib.php b/lib/moodlelib.php
index d00252caba9..462aea614be 100644
--- a/lib/moodlelib.php
+++ b/lib/moodlelib.php
@@ -10243,23 +10243,12 @@ function is_proxybypass( $url ) {
     // Get the possible bypass hosts into an array.
     $matches = explode( ',', $CFG->proxybypass );
 
-    // Check for a match.
-    // (IPs need to match the left hand side and hosts the right of the url,
-    // but we can recklessly check both as there can't be a false +ve).
-    foreach ($matches as $match) {
-        $match = trim($match);
+    // Check for a exact match on the IP or in the domains.
+    $isdomaininallowedlist = \core\ip_utils::is_domain_in_allowed_list($host, $matches);
+    $isipinsubnetlist = \core\ip_utils::is_ip_in_subnet_list($host, $CFG->proxybypass, ',');
 
-        // Try for IP match (Left side).
-        $lhs = substr($host, 0, strlen($match));
-        if (strcasecmp($match, $lhs)==0) {
-            return true;
-        }
-
-        // Try for host match (Right side).
-        $rhs = substr($host, -strlen($match));
-        if (strcasecmp($match, $rhs)==0) {
-            return true;
-        }
+    if ($isdomaininallowedlist || $isipinsubnetlist) {
+        return true;
     }
 
     // Nothing matched.
diff --git a/lib/tests/moodlelib_test.php b/lib/tests/moodlelib_test.php
index bc8ac172a8e..1bdc12e732b 100644
--- a/lib/tests/moodlelib_test.php
+++ b/lib/tests/moodlelib_test.php
@@ -5522,4 +5522,70 @@ EOT;
         $this->assertEquals(false, html_is_blank('<p>.</p>'));
         $this->assertEquals(false, html_is_blank('<img src="#">'));
     }
+
+    /**
+     * Provider for is_proxybypass
+     *
+     * @return array of test cases.
+     */
+    public function is_proxybypass_provider(): array {
+
+        return [
+            'Proxybypass contains the same IP as the beginning of the URL' => [
+                'http://192.168.5.5-fake-app-7f000101.nip.io',
+                '192.168.5.5, 127.0.0.1',
+                false
+            ],
+            'Proxybypass contains the last part of the URL' => [
+                'http://192.168.5.5-fake-app-7f000101.nip.io',
+                'app-7f000101.nip.io',
+                false
+            ],
+            'Proxybypass contains the last part of the URL 2' => [
+                'http://store.mydomain.com',
+                'mydomain.com',
+                false
+            ],
+            'Proxybypass contains part of the url' => [
+                'http://myweb.com',
+                'store.myweb.com',
+                false
+            ],
+            'Different IPs used in proxybypass' => [
+                'http://192.168.5.5',
+                '192.168.5.3',
+                false
+            ],
+            'Proxybypass and URL matchs' => [
+                'http://store.mydomain.com',
+                'store.mydomain.com',
+                true
+            ],
+            'IP used in proxybypass' => [
+                'http://192.168.5.5',
+                '192.168.5.5',
+                true
+            ],
+        ];
+    }
+
+    /**
+     * Check if $url matches anything in proxybypass list
+     *
+     * Test function {@see is_proxybypass()}.
+     * @dataProvider is_proxybypass_provider
+     * @param string $url url to check
+     * @param string $proxybypass
+     * @param bool $expected Expected value.
+     */
+    public function test_is_proxybypass(string $url, string $proxybypass, bool $expected): void {
+        $this->resetAfterTest();
+
+        global $CFG;
+        $CFG->proxyhost = '192.168.5.5'; // Test with a fake proxy.
+        $CFG->proxybypass = $proxybypass;
+
+        $this->assertEquals($expected, is_proxybypass($url));
+    }
+
 }