diff --git a/lib/private/Net/HostnameClassifier.php b/lib/private/Net/HostnameClassifier.php
index e0f1435d6f167..13acca326ddfc 100644
--- a/lib/private/Net/HostnameClassifier.php
+++ b/lib/private/Net/HostnameClassifier.php
@@ -38,6 +38,7 @@ class HostnameClassifier {
 	 * IP addresses are not considered local. Use the IpAddressClassifier for those.
 	 */
 	public function isLocalHostname(string $hostname): bool {
+		$hostname = rtrim($hostname, '.');
 		// Disallow local network top-level domains from RFC 6762
 		$topLevelDomain = substr((strrchr($hostname, '.') ?: ''), 1);
 		if (in_array($topLevelDomain, self::LOCAL_TOPLEVEL_DOMAINS)) {
diff --git a/lib/private/Net/IpAddressClassifier.php b/lib/private/Net/IpAddressClassifier.php
index 9d701b21e4199..d7563f3529961 100644
--- a/lib/private/Net/IpAddressClassifier.php
+++ b/lib/private/Net/IpAddressClassifier.php
@@ -13,6 +13,8 @@
 use IPLib\Address\IPv6;
 use IPLib\Factory;
 use IPLib\ParseStringFlag;
+use IPLib\Range\RangeInterface;
+use IPLib\Range\Subnet;
 use Symfony\Component\HttpFoundation\IpUtils;
 use function filter_var;
 
@@ -27,12 +29,48 @@ class IpAddressClassifier {
 		'192.0.0.0/24', // See RFC 6890
 	];
 
+	private RangeInterface $nat64Range;
+	private RangeInterface $rfc8215;
+	private RangeInterface $teredo;
+	private RangeInterface $ipv4Compatible;
+
+	public function __construct() {
+		$this->nat64Range = Subnet::parseString('64:ff9b::/96');
+		$this->rfc8215 = Subnet::parseString('64:ff9b:1::/48');
+		$this->teredo = Subnet::parseString('2001::/32');
+		$this->ipv4Compatible = Subnet::parseString('::0:0/96');
+	}
+
+	/**
+	 * Get the ipv4 that an ipv6 address maps to, if any.
+	 *
+	 * Note that this is not just ipv6 representations of ipv4 addresses,
+	 * but also any NAT or proxy style translation addresses
+	 */
+	public function getMappedIpv4(IPv6 $ip): ?IPv4 {
+		$ipv4 = $ip->toIPv4();
+		$ipv6Bytes = $ip->getBytes();
+		if ($ipv4) {
+			return $ipv4;
+		} elseif ($this->nat64Range->contains($ip)) {
+			return IPv4::fromBytes(array_slice($ipv6Bytes, -4, 4));
+		} elseif ($this->ipv4Compatible->contains($ip)) {
+			return IPv4::fromBytes(array_slice($ipv6Bytes, -4, 4));
+		} elseif ($this->teredo->contains($ip)) {
+			$xorBytes = array_slice($ipv6Bytes, -4, 4);
+			return IPv4::fromBytes(array_map(fn (int $byte) => $byte ^ 0xFF, $xorBytes));
+		}
+
+		return null;
+	}
+
 	/**
 	 * Check host identifier for local IPv4 and IPv6 address ranges
 	 *
 	 * Hostnames are not considered local. Use the HostnameClassifier for those.
 	 */
 	public function isLocalAddress(string $ip): bool {
+		$ip = rtrim($ip, '.');
 		$parsedIp = Factory::parseAddressString(
 			$ip,
 			ParseStringFlag::IPV4_MAYBE_NON_DECIMAL | ParseStringFlag::IPV4ADDRESS_MAYBE_NON_QUAD_DOTTED | ParseStringFlag::MAY_INCLUDE_ZONEID
@@ -43,12 +81,16 @@ public function isLocalAddress(string $ip): bool {
 		}
 		/* Replace by normalized form */
 		if ($parsedIp instanceof IPv6) {
-			$ipv4 = $parsedIp->toIPv4();
-			$ipv6Bytes = $parsedIp->getBytes();
+			// rfc8215 is a generic reservation for ipv6/ipv4 translation mechanisms,
+			// no assumptions can be made about how ipv4 addresses are encoded within.
+			//
+			// Thus the only thing we can do is treat them all as local
+			if ($this->rfc8215->contains($parsedIp)) {
+				return true;
+			}
+			$ipv4 = $this->getMappedIpv4($parsedIp);
 			if ($ipv4) {
 				$ip = (string)$ipv4;
-			} elseif (array_slice($ipv6Bytes, 0, 4) === [0x00, 0x64, 0xFF, 0x9B]) {
-				$ip = (string)IPv4::fromBytes(array_slice($ipv6Bytes, -4, 4));
 			} else {
 				$ip = (string)$parsedIp;
 			}
diff --git a/lib/private/Security/RemoteHostValidator.php b/lib/private/Security/RemoteHostValidator.php
index 459bcb8d512e8..db491ad444023 100644
--- a/lib/private/Security/RemoteHostValidator.php
+++ b/lib/private/Security/RemoteHostValidator.php
@@ -36,6 +36,8 @@ public function isValid(string $host): bool {
 			return true;
 		}
 
+		$host = rtrim($host, '.');
+
 		$host = idn_to_utf8(strtolower(urldecode($host)));
 		if ($host === false) {
 			return false;
diff --git a/tests/lib/Net/HostnameClassifierTest.php b/tests/lib/Net/HostnameClassifierTest.php
index 656ad4f54a535..90e16a17b23df 100644
--- a/tests/lib/Net/HostnameClassifierTest.php
+++ b/tests/lib/Net/HostnameClassifierTest.php
@@ -30,6 +30,7 @@ public static function localHostnamesData(): array {
 			['another-host.local'],
 			['service.localhost'],
 			['randomdomain.internal'],
+			['another-host.local.'],
 		];
 	}
 
@@ -47,6 +48,7 @@ public static function publicHostnamesData(): array {
 			['example.org'],
 			['host.domain'],
 			['cloud.domain.tld'],
+			['cloud.domain.tld.'],
 		];
 	}
 
diff --git a/tests/lib/Net/IpAddressClassifierTest.php b/tests/lib/Net/IpAddressClassifierTest.php
index d4d8bf5cd223a..9fe35453b05c1 100644
--- a/tests/lib/Net/IpAddressClassifierTest.php
+++ b/tests/lib/Net/IpAddressClassifierTest.php
@@ -9,6 +9,8 @@
 
 namespace lib\Net;
 
+use IPLib\Address\IPv4;
+use IPLib\Address\IPv6;
 use OC\Net\IpAddressClassifier;
 use Test\TestCase;
 
@@ -53,6 +55,10 @@ public static function localIpAddressData(): array {
 			['100.100.100.200'],
 			['192.0.0.1'],
 			['64:ff9b::a9fe:a9fe'], // NAT64 of 169.254.169.254
+			['::ffff:127.0.0.1'],
+			['2130706433'],
+			['0177.0.0.1'],
+			['169.254.169.254'],
 		];
 	}
 
@@ -62,4 +68,26 @@ public function testLocalAddress(string $ip): void {
 
 		self::assertTrue($isLocal);
 	}
+
+	public static function mappedAddresses(): array {
+		return [
+			['64:ff9b::a9fe:a9fe', '169.254.169.254'],
+			['::ffff:7f00:1', '127.0.0.1'],
+			['::127.0.0.1', '127.0.0.1'],
+			['::7f00:1', '127.0.0.1'],
+			['2001:0000:4136:e378:8000:63bf:3fff:fdd2', '192.0.2.45'],
+			['2001:4860:4860::8888', null],
+		];
+	}
+
+	#[\PHPUnit\Framework\Attributes\DataProvider('mappedAddresses')]
+	public function testMappedAddresses(string $ipv6, ?string $ipv4): void {
+		$mapped = $this->classifier->getMappedIpv4(IPv6::parseString($ipv6));
+
+		if ($ipv4 === null) {
+			self::assertEquals(null, $mapped);
+		} else {
+			self::assertEquals(IPv4::parseString($ipv4), $mapped);
+		}
+	}
 }