diff --git a/apps/settings/lib/Controller/ChangePasswordController.php b/apps/settings/lib/Controller/ChangePasswordController.php
index 7c3ab9546bc59..41f2584721cd8 100644
--- a/apps/settings/lib/Controller/ChangePasswordController.php
+++ b/apps/settings/lib/Controller/ChangePasswordController.php
@@ -107,7 +107,7 @@ public function changePersonalPassword(string $oldpassword = '', string $newpass
 		}
 
 		try {
-			if ($newpassword === null || $user->setPassword($newpassword) === false) {
+			if ($newpassword === null || strlen($newpassword) > 469 || $user->setPassword($newpassword) === false) {
 				return new JSONResponse([
 					'status' => 'error',
 					'data' => [
@@ -158,6 +158,15 @@ public function changeUserPassword(string $username = null, string $password = n
 			]);
 		}
 
+		if (strlen($password) > 469) {
+			return new JSONResponse([
+				'status' => 'error',
+				'data' => [
+					'message' => $this->l->t('Unable to change password. Password too long.'),
+				],
+			]);
+		}
+
 		$currentUser = $this->userSession->getUser();
 		$targetUser = $this->userManager->get($username);
 		if ($currentUser === null || $targetUser === null ||
diff --git a/apps/settings/src/components/UserList/UserRow.vue b/apps/settings/src/components/UserList/UserRow.vue
index de0a09f2221de..f2947019f40bf 100644
--- a/apps/settings/src/components/UserList/UserRow.vue
+++ b/apps/settings/src/components/UserList/UserRow.vue
@@ -107,6 +107,7 @@
 				ref="password"
 				:disabled="loading.password || loading.all"
 				:minlength="minPasswordLength"
+				maxlength="469"
 				:placeholder="t('settings', 'Add new password')"
 				autocapitalize="off"
 				autocomplete="new-password"
diff --git a/apps/settings/templates/settings/personal/security/password.php b/apps/settings/templates/settings/personal/security/password.php
index 88536ab6b238a..85959e252ccdf 100644
--- a/apps/settings/templates/settings/personal/security/password.php
+++ b/apps/settings/templates/settings/personal/security/password.php
@@ -46,6 +46,7 @@
 				<div class="personal-show-container">
 					<label for="pass2" class="hidden-visually"><?php p($l->t('New password'));?>: </label>
 					<input type="password" id="pass2" name="newpassword"
+						   maxlength="469"
 						   placeholder="<?php p($l->t('New password')); ?>"
 						   data-typetoggle="#personal-show"
 						   autocomplete="new-password" autocapitalize="none" autocorrect="off" />
diff --git a/config/config.sample.php b/config/config.sample.php
index 9856aeba4d725..025cf1105a01a 100644
--- a/config/config.sample.php
+++ b/config/config.sample.php
@@ -308,6 +308,21 @@
  */
 'auth.webauthn.enabled' => true,
 
+/**
+ * Whether encrypted password should be stored in the database
+ *
+ * The passwords are only decrypted using the login token stored uniquely in the
+ * clients and allow to connect to external storages, autoconfigure mail account in
+ * the mail app and periodically check if the password it still valid.
+ *
+ * This might be desirable to disable this functionality when using one time
+ * passwords or when having a password policy enforcing long passwords (> 300
+ * characters).
+ *
+ * By default the passwords are stored encrypted in the database.
+ */
+'auth.storeCryptedPassword' => true,
+
 /**
  * By default the login form is always available. There are cases (SSO) where an
  * admin wants to avoid users entering their credentials to the system if the SSO
diff --git a/lib/private/Authentication/Token/PublicKeyTokenProvider.php b/lib/private/Authentication/Token/PublicKeyTokenProvider.php
index a1d75828e2758..96bf9a8608798 100644
--- a/lib/private/Authentication/Token/PublicKeyTokenProvider.php
+++ b/lib/private/Authentication/Token/PublicKeyTokenProvider.php
@@ -346,7 +346,7 @@ private function newToken(string $token,
 
 		$config = array_merge([
 			'digest_alg' => 'sha512',
-			'private_key_bits' => 2048,
+			'private_key_bits' => $password !== null && strlen($password) > 250 ? 4096 : 2048,
 		], $this->config->getSystemValue('openssl', []));
 
 		// Generate new key
@@ -368,7 +368,10 @@ private function newToken(string $token,
 		$dbToken->setPublicKey($publicKey);
 		$dbToken->setPrivateKey($this->encrypt($privateKey, $token));
 
-		if (!is_null($password)) {
+		if (!is_null($password) && $this->config->getSystemValueBool('auth.storeCryptedPassword', true)) {
+			if (strlen($password) > 469) {
+				throw new \RuntimeException('Trying to save a password with more than 469 characters is not supported. If you want to use big passwords, disable the auth.storeCryptedPassword option in config.php');
+			}
 			$dbToken->setPassword($this->encryptPassword($password, $publicKey));
 		}
 
diff --git a/tests/lib/Authentication/Token/PublicKeyTokenProviderTest.php b/tests/lib/Authentication/Token/PublicKeyTokenProviderTest.php
index 6ad57515c1627..db61244db5b65 100644
--- a/tests/lib/Authentication/Token/PublicKeyTokenProviderTest.php
+++ b/tests/lib/Authentication/Token/PublicKeyTokenProviderTest.php
@@ -25,6 +25,7 @@
 
 use OC\Authentication\Exceptions\ExpiredTokenException;
 use OC\Authentication\Exceptions\InvalidTokenException;
+use OC\Authentication\Exceptions\PasswordlessTokenException;
 use OC\Authentication\Token\IToken;
 use OC\Authentication\Token\PublicKeyToken;
 use OC\Authentication\Token\PublicKeyTokenMapper;
@@ -83,6 +84,10 @@ public function testGenerateToken() {
 		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
 		$type = IToken::PERMANENT_TOKEN;
 
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
 		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
 
 		$this->assertInstanceOf(PublicKeyToken::class, $actual);
@@ -93,6 +98,48 @@ public function testGenerateToken() {
 		$this->assertSame($password, $this->tokenProvider->getPassword($actual, $token));
 	}
 
+	public function testGenerateTokenNoPassword() {
+		$token = 'token';
+		$uid = 'user';
+		$user = 'User';
+		$password = 'passme';
+		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
+		$type = IToken::PERMANENT_TOKEN;
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, false],
+			]);
+		$this->expectException(PasswordlessTokenException::class);
+
+		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
+
+		$this->assertInstanceOf(PublicKeyToken::class, $actual);
+		$this->assertSame($uid, $actual->getUID());
+		$this->assertSame($user, $actual->getLoginName());
+		$this->assertSame($name, $actual->getName());
+		$this->assertSame(IToken::DO_NOT_REMEMBER, $actual->getRemember());
+		$this->tokenProvider->getPassword($actual, $token);
+	}
+
+	public function testGenerateTokenLongPassword() {
+		$token = 'token';
+		$uid = 'user';
+		$user = 'User';
+		$password = '';
+		for ($i = 0; $i < 500; $i++) {
+			$password .= 'e';
+		}
+		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
+		$type = IToken::PERMANENT_TOKEN;
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
+		$this->expectException(\RuntimeException::class);
+
+		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
+	}
+
 	public function testGenerateTokenInvalidName() {
 		$token = 'token';
 		$uid = 'user';
@@ -103,6 +150,10 @@ public function testGenerateTokenInvalidName() {
 			. 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12'
 			. 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
 		$type = IToken::PERMANENT_TOKEN;
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
 
 		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
 
@@ -157,6 +208,10 @@ public function testGetPassword() {
 		$password = 'passme';
 		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
 		$type = IToken::PERMANENT_TOKEN;
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
 
 		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
 
@@ -185,6 +240,10 @@ public function testGetPasswordInvalidToken() {
 		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
 		$type = IToken::PERMANENT_TOKEN;
 
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
 		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
 
 		$this->tokenProvider->getPassword($actual, 'wrongtoken');
@@ -197,6 +256,10 @@ public function testSetPassword() {
 		$password = 'passme';
 		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
 		$type = IToken::PERMANENT_TOKEN;
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
 
 		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
 
@@ -301,7 +364,7 @@ public function testRenewSessionTokenWithoutPassword() {
 		$this->tokenProvider->renewSessionToken('oldId', 'newId');
 	}
 
-	public function testRenewSessionTokenWithPassword() {
+	public function testRenewSessionTokenWithPassword(): void {
 		$token = 'oldId';
 		$uid = 'user';
 		$user = 'User';
@@ -309,6 +372,10 @@ public function testRenewSessionTokenWithPassword() {
 		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
 		$type = IToken::PERMANENT_TOKEN;
 
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
 		$oldToken = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
 
 		$this->mapper
@@ -319,7 +386,7 @@ public function testRenewSessionTokenWithPassword() {
 		$this->mapper
 			->expects($this->once())
 			->method('insert')
-			->with($this->callback(function (PublicKeyToken $token) use ($user, $uid, $name) {
+			->with($this->callback(function (PublicKeyToken $token) use ($user, $uid, $name): bool {
 				return $token->getUID() === $uid &&
 					$token->getLoginName() === $user &&
 					$token->getName() === $name &&
@@ -331,14 +398,14 @@ public function testRenewSessionTokenWithPassword() {
 		$this->mapper
 			->expects($this->once())
 			->method('delete')
-			->with($this->callback(function ($token) use ($oldToken) {
+			->with($this->callback(function ($token) use ($oldToken): bool {
 				return $token === $oldToken;
 			}));
 
 		$this->tokenProvider->renewSessionToken('oldId', 'newId');
 	}
 
-	public function testGetToken() {
+	public function testGetToken(): void {
 		$token = new PublicKeyToken();
 
 		$this->config->method('getSystemValue')
@@ -441,6 +508,10 @@ public function testRotate() {
 		$name = 'User-Agent: Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv:1.9.2.12) Gecko/20101026 Firefox/3.6.12';
 		$type = IToken::PERMANENT_TOKEN;
 
+		$this->config->method('getSystemValueBool')
+			->willReturnMap([
+				['auth.storeCryptedPassword', true, true],
+			]);
 		$actual = $this->tokenProvider->generateToken($token, $uid, $user, $password, $name, $type, IToken::DO_NOT_REMEMBER);
 
 		$new = $this->tokenProvider->rotate($actual, 'oldtoken', 'newtoken');