diff --git a/lib/private/Session/Internal.php b/lib/private/Session/Internal.php
index d10091011573c..4d31d684adede 100644
--- a/lib/private/Session/Internal.php
+++ b/lib/private/Session/Internal.php
@@ -12,6 +12,7 @@
 
 use OC\Authentication\Token\IProvider;
 use OC\Diagnostics\TLogSlowOperation;
+use OC\User\Session as UserSession;
 use OCP\Authentication\Exceptions\InvalidTokenException;
 use OCP\Server;
 use OCP\Session\Exceptions\SessionNotAvailableException;
@@ -149,6 +150,7 @@ public function regenerateId(bool $deleteOldSession = true, bool $updateToken =
 
 			try {
 				$tokenProvider->renewSessionToken($oldId, $newId);
+				Server::get(UserSession::class)->renewMagicSessionId($oldId);
 			} catch (InvalidTokenException $e) {
 				// Just ignore
 			}
diff --git a/lib/private/User/Session.php b/lib/private/User/Session.php
index 578f8e75b9e25..7bb68ef3df835 100644
--- a/lib/private/User/Session.php
+++ b/lib/private/User/Session.php
@@ -977,6 +977,17 @@ public function loginWithCookie($uid, $currentToken, $oldSessionId) {
 	 * @param IUser $user
 	 */
 	public function createRememberMeToken(IUser $user) {
+		// The cookie outlives the session lifetime, so its token must not be
+		// cleaned up as a short-lived one.
+		try {
+			$sessionToken = $this->tokenProvider->getToken($this->session->getId());
+			if ($sessionToken instanceof PublicKeyToken && $sessionToken->getRemember() !== IToken::REMEMBER) {
+				$sessionToken->setRemember(IToken::REMEMBER);
+				$this->tokenProvider->updateToken($sessionToken);
+			}
+		} catch (InvalidTokenException|SessionNotAvailableException) {
+		}
+
 		$token = $this->random->generate(32);
 		$this->config->setUserValue($user->getUID(), 'login_token', $token, (string)$this->timeFactory->getTime());
 		$this->setMagicInCookie($user->getUID(), $token);
@@ -1061,6 +1072,18 @@ public function setMagicInCookie($username, $token) {
 		}
 	}
 
+	/**
+	 * Point the remember-me cookie at the regenerated session id, so cookie
+	 * login can still find the token that was renewed along with it.
+	 */
+	public function renewMagicSessionId(string $oldSessionId): void {
+		if (!isset($_COOKIE['nc_username'], $_COOKIE['nc_token'], $_COOKIE['nc_session_id'])
+			|| $_COOKIE['nc_session_id'] !== $oldSessionId) {
+			return;
+		}
+		$this->setMagicInCookie($_COOKIE['nc_username'], $_COOKIE['nc_token']);
+	}
+
 	/**
 	 * Remove cookie for "remember username"
 	 */
diff --git a/tests/lib/User/SessionTest.php b/tests/lib/User/SessionTest.php
index f466569eb9b3c..d0ba56df49f2f 100644
--- a/tests/lib/User/SessionTest.php
+++ b/tests/lib/User/SessionTest.php
@@ -1211,6 +1211,67 @@ public function testCreateRememberMeToken(): void {
 		$this->userSession->createRememberMeToken($user);
 	}
 
+	public static function rememberMeSessionTokenData(): array {
+		return [
+			'session token that is not remembered is upgraded' => [IToken::DO_NOT_REMEMBER, true],
+			'remembered session token is left alone' => [IToken::REMEMBER, false],
+		];
+	}
+
+	#[\PHPUnit\Framework\Attributes\DataProvider(methodName: 'rememberMeSessionTokenData')]
+	public function testCreateRememberMeTokenRemembersSessionToken(int $remember, bool $expectUpdate): void {
+		$user = $this->createMock(IUser::class);
+		$user->method('getUID')->willReturn('UserUid');
+		$this->session->method('getId')->willReturn('sessionid');
+		$token = new PublicKeyToken();
+		$token->setRemember($remember);
+		$this->tokenProvider->method('getToken')
+			->with('sessionid')
+			->willReturn($token);
+		$this->tokenProvider->expects($expectUpdate ? $this->once() : $this->never())
+			->method('updateToken')
+			->with($this->callback(fn (PublicKeyToken $t): bool => $t->getRemember() === IToken::REMEMBER));
+
+		$this->userSession->createRememberMeToken($user);
+	}
+
+	public function testCreateRememberMeTokenWithoutSessionToken(): void {
+		$user = $this->createMock(IUser::class);
+		$user->method('getUID')->willReturn('UserUid');
+		$this->random->method('generate')->willReturn('LongRandomToken');
+		$this->session->method('getId')->willReturn('sessionid');
+		$this->tokenProvider->method('getToken')->willThrowException(new InvalidTokenException());
+		$this->tokenProvider->expects($this->never())->method('updateToken');
+		$this->userSession->expects($this->once())
+			->method('setMagicInCookie')
+			->with('UserUid', 'LongRandomToken');
+
+		$this->userSession->createRememberMeToken($user);
+	}
+
+	public static function renewMagicSessionIdData(): array {
+		return [
+			'cookie holds the old session id' => [['nc_username' => 'u', 'nc_token' => 't', 'nc_session_id' => 'old'], true],
+			'cookie holds another session id' => [['nc_username' => 'u', 'nc_token' => 't', 'nc_session_id' => 'other'], false],
+			'no remember-me cookies' => [[], false],
+		];
+	}
+
+	#[\PHPUnit\Framework\Attributes\DataProvider(methodName: 'renewMagicSessionIdData')]
+	public function testRenewMagicSessionId(array $cookies, bool $expectRenewal): void {
+		$this->userSession->expects($expectRenewal ? $this->once() : $this->never())
+			->method('setMagicInCookie')
+			->with('u', 't');
+
+		$originalCookies = $_COOKIE;
+		$_COOKIE = $cookies;
+		try {
+			$this->userSession->renewMagicSessionId('old');
+		} finally {
+			$_COOKIE = $originalCookies;
+		}
+	}
+
 	public function testTryBasicAuthLoginValid(): void {
 		$request = $this->createMock(Request::class);
 		$request->method('__get')