diff --git a/third_party/astrolabe/appinfo/info.xml b/third_party/astrolabe/appinfo/info.xml
index 1992b8f..31209a6 100644
--- a/third_party/astrolabe/appinfo/info.xml
+++ b/third_party/astrolabe/appinfo/info.xml
@@ -57,4 +57,7 @@ See [documentation](https://github.com/cbcoutinho/nextcloud-mcp-server) for conf
 			<type>link</type>
 		</navigation>
 	</navigations>
+	<background-jobs>
+		<job>OCA\Astrolabe\BackgroundJob\RefreshUserTokens</job>
+	</background-jobs>
 </info>
diff --git a/third_party/astrolabe/lib/BackgroundJob/RefreshUserTokens.php b/third_party/astrolabe/lib/BackgroundJob/RefreshUserTokens.php
new file mode 100644
index 0000000..c79add2
--- /dev/null
+++ b/third_party/astrolabe/lib/BackgroundJob/RefreshUserTokens.php
@@ -0,0 +1,155 @@
+<?php
+
+declare(strict_types=1);
+
+namespace OCA\Astrolabe\BackgroundJob;
+
+use OCA\Astrolabe\Service\IdpTokenRefresher;
+use OCA\Astrolabe\Service\McpTokenStorage;
+use OCP\AppFramework\Utility\ITimeFactory;
+use OCP\BackgroundJob\IJob;
+use OCP\BackgroundJob\TimedJob;
+use Psr\Log\LoggerInterface;
+
+/**
+ * Background job to proactively refresh OAuth tokens before expiration.
+ *
+ * Runs every 15 minutes and refreshes tokens based on their actual expiration
+ * time. Works with any IdP (Nextcloud OIDC, Keycloak, etc.) since it uses
+ * the real token expiration rather than IdP configuration.
+ *
+ * Refresh strategy: Refresh when less than 50% of token lifetime remains,
+ * ensuring tokens are refreshed well before expiration regardless of the
+ * IdP's configured token lifetime.
+ *
+ * @psalm-suppress UnusedClass - Background jobs are loaded dynamically by Nextcloud
+ */
+class RefreshUserTokens extends TimedJob {
+	/** Job runs every 15 minutes */
+	private const JOB_INTERVAL_SECONDS = 900;
+
+	/** Refresh when this percentage of token lifetime remains */
+	private const REFRESH_AT_REMAINING_PERCENT = 0.5;
+
+	/** Minimum threshold to avoid constant refresh (5 minutes) */
+	private const MIN_THRESHOLD_SECONDS = 300;
+
+	/** Default assumed token lifetime if we can't determine it (1 hour) */
+	private const DEFAULT_TOKEN_LIFETIME_SECONDS = 3600;
+
+	public function __construct(
+		ITimeFactory $time,
+		private McpTokenStorage $tokenStorage,
+		private IdpTokenRefresher $tokenRefresher,
+		private LoggerInterface $logger,
+	) {
+		parent::__construct($time);
+		$this->setInterval(self::JOB_INTERVAL_SECONDS);
+		$this->setTimeSensitivity(IJob::TIME_INSENSITIVE);
+	}
+
+	protected function run(mixed $argument): void {
+		$this->logger->info('RefreshUserTokens: Starting background token refresh');
+
+		$userIds = $this->tokenStorage->getAllUsersWithTokens();
+		$this->logger->debug('RefreshUserTokens: Found ' . count($userIds) . ' users with tokens');
+
+		$refreshed = 0;
+		$failed = 0;
+		$skipped = 0;
+
+		foreach ($userIds as $userId) {
+			$result = $this->refreshUserTokenIfNeeded($userId);
+			match ($result) {
+				'refreshed' => $refreshed++,
+				'failed' => $failed++,
+				'skipped' => $skipped++,
+			};
+		}
+
+		$this->logger->info("RefreshUserTokens: Complete - refreshed=$refreshed, failed=$failed, skipped=$skipped");
+	}
+
+	/**
+	 * Refresh a user's token if it's nearing expiration.
+	 *
+	 * Calculates the refresh threshold based on the token's actual lifetime,
+	 * refreshing when less than 50% of the lifetime remains.
+	 *
+	 * @return string 'refreshed', 'failed', or 'skipped'
+	 */
+	private function refreshUserTokenIfNeeded(string $userId): string {
+		$token = $this->tokenStorage->getUserToken($userId);
+
+		if ($token === null) {
+			return 'skipped';
+		}
+
+		$expiresAt = (int)($token['expires_at'] ?? 0);
+		$issuedAt = isset($token['issued_at']) ? (int)$token['issued_at'] : null;
+		$timeRemaining = $expiresAt - time();
+
+		// Calculate token lifetime from stored data or use default
+		if ($issuedAt !== null) {
+			$tokenLifetime = $expiresAt - $issuedAt;
+		} else {
+			// Fallback: use default lifetime assumption
+			$tokenLifetime = self::DEFAULT_TOKEN_LIFETIME_SECONDS;
+		}
+
+		// Calculate threshold: refresh when 50% of lifetime remains
+		$threshold = max(
+			(int)($tokenLifetime * self::REFRESH_AT_REMAINING_PERCENT),
+			self::MIN_THRESHOLD_SECONDS
+		);
+
+		if ($timeRemaining > $threshold) {
+			// Token still has plenty of time, skip
+			return 'skipped';
+		}
+
+		// Token is expiring soon, attempt refresh
+		if (!isset($token['refresh_token'])) {
+			$this->logger->warning("RefreshUserTokens: User $userId has no refresh token");
+			return 'failed';
+		}
+
+		$this->logger->debug("RefreshUserTokens: Refreshing token for user $userId (remaining={$timeRemaining}s, threshold={$threshold}s)");
+
+		try {
+			/** @var string $refreshToken */
+			$refreshToken = $token['refresh_token'];
+			$newTokenData = $this->tokenRefresher->refreshAccessToken($refreshToken);
+
+			if ($newTokenData === null) {
+				$this->logger->warning("RefreshUserTokens: Refresh returned null for user $userId");
+				// Don't delete token here - let on-demand refresh handle cleanup
+				return 'failed';
+			}
+
+			// Calculate new expiration and store issued_at for future calculations
+			$expiresIn = (int)($newTokenData['expires_in'] ?? self::DEFAULT_TOKEN_LIFETIME_SECONDS);
+			$now = time();
+
+			/** @var string $accessToken */
+			$accessToken = $newTokenData['access_token'];
+			/** @var string $newRefreshToken */
+			$newRefreshToken = $newTokenData['refresh_token'] ?? $refreshToken;
+
+			$this->tokenStorage->storeUserToken(
+				$userId,
+				$accessToken,
+				$newRefreshToken,
+				$now + $expiresIn,
+				$now  // issued_at
+			);
+
+			$this->logger->debug("RefreshUserTokens: Successfully refreshed token for user $userId");
+			return 'refreshed';
+
+		} catch (\Exception $e) {
+			$this->logger->error("RefreshUserTokens: Failed to refresh for user $userId: " . $e->getMessage());
+			return 'failed';
+		}
+	}
+}
diff --git a/third_party/astrolabe/lib/Search/SemanticSearchProvider.php b/third_party/astrolabe/lib/Search/SemanticSearchProvider.php
index 8da0cb4..bdcb2f0 100644
--- a/third_party/astrolabe/lib/Search/SemanticSearchProvider.php
+++ b/third_party/astrolabe/lib/Search/SemanticSearchProvider.php
@@ -5,6 +5,7 @@ declare(strict_types=1);
 namespace OCA\Astrolabe\Search;
 
 use OCA\Astrolabe\AppInfo\Application;
+use OCA\Astrolabe\Service\IdpTokenRefresher;
 use OCA\Astrolabe\Service\McpServerClient;
 use OCA\Astrolabe\Service\McpTokenStorage;
 use OCA\Astrolabe\Settings\Admin as AdminSettings;
@@ -35,6 +36,7 @@ class SemanticSearchProvider implements IProvider {
 	public function __construct(
 		private McpServerClient $client,
 		private McpTokenStorage $tokenStorage,
+		private IdpTokenRefresher $tokenRefresher,
 		private IConfig $config,
 		private IL10N $l10n,
 		private IURLGenerator $urlGenerator,
@@ -85,12 +87,30 @@ class SemanticSearchProvider implements IProvider {
 			return SearchResult::complete($this->getName(), []);
 		}
 
-		// Get OAuth token for user
-		$accessToken = $this->tokenStorage->getAccessToken($user->getUID());
+		$userId = $user->getUID();
+
+		// Create refresh callback matching ApiController pattern
+		/** @return array{access_token: string, refresh_token: string, expires_in: int}|null */
+		$refreshCallback = function (string $refreshToken): ?array {
+			$newTokenData = $this->tokenRefresher->refreshAccessToken($refreshToken);
+
+			if ($newTokenData === null) {
+				return null;
+			}
+
+			return [
+				'access_token' => $newTokenData['access_token'],
+				'refresh_token' => $newTokenData['refresh_token'] ?? $refreshToken,
+				'expires_in' => $newTokenData['expires_in'] ?? 3600,
+			];
+		};
+
+		// Get OAuth token for user with automatic refresh
+		$accessToken = $this->tokenStorage->getAccessToken($userId, $refreshCallback);
 		if ($accessToken === null) {
 			// User hasn't authorized the app yet - return empty results
 			$this->logger->debug('No OAuth token for user in semantic search', [
-				'user_id' => $user->getUID(),
+				'user_id' => $userId,
 			]);
 			return SearchResult::complete($this->getName(), []);
 		}
diff --git a/third_party/astrolabe/lib/Service/McpTokenStorage.php b/third_party/astrolabe/lib/Service/McpTokenStorage.php
index 5d499fa..8c36211 100644
--- a/third_party/astrolabe/lib/Service/McpTokenStorage.php
+++ b/third_party/astrolabe/lib/Service/McpTokenStorage.php
@@ -5,6 +5,7 @@ declare(strict_types=1);
 namespace OCA\Astrolabe\Service;
 
 use OCP\IConfig;
+use OCP\IDBConnection;
 use OCP\Security\ICrypto;
 use Psr\Log\LoggerInterface;
 
@@ -20,15 +21,18 @@ class McpTokenStorage {
 
 	private $config;
 	private $crypto;
+	private $db;
 	private $logger;
 
 	public function __construct(
 		IConfig $config,
 		ICrypto $crypto,
+		IDBConnection $db,
 		LoggerInterface $logger,
 	) {
 		$this->config = $config;
 		$this->crypto = $crypto;
+		$this->db = $db;
 		$this->logger = $logger;
 	}
 
@@ -41,18 +45,21 @@ class McpTokenStorage {
 	 * @param string $accessToken OAuth access token
 	 * @param string $refreshToken OAuth refresh token
 	 * @param int $expiresAt Unix timestamp when token expires
+	 * @param int|null $issuedAt Unix timestamp when token was issued (for lifetime calculation)
 	 */
 	public function storeUserToken(
 		string $userId,
 		string $accessToken,
 		string $refreshToken,
 		int $expiresAt,
+		?int $issuedAt = null,
 	): void {
 		try {
 			$tokenData = [
 				'access_token' => $accessToken,
 				'refresh_token' => $refreshToken,
 				'expires_at' => $expiresAt,
+				'issued_at' => $issuedAt ?? time(),
 			];
 
 			// Encrypt token data before storage
@@ -153,6 +160,35 @@ class McpTokenStorage {
 		}
 	}
 
+	/**
+	 * Get all user IDs that have OAuth tokens stored.
+	 *
+	 * Queries oc_preferences directly since IConfig doesn't support
+	 * listing all users with a specific key set.
+	 *
+	 * @return list<string> Array of user IDs
+	 */
+	public function getAllUsersWithTokens(): array {
+		$qb = $this->db->getQueryBuilder();
+		$qb->select('userid')
+			->from('preferences')
+			->where($qb->expr()->eq('appid', $qb->createNamedParameter('astrolabe')))
+			->andWhere($qb->expr()->eq('configkey', $qb->createNamedParameter('oauth_tokens')));
+
+		$result = $qb->executeQuery();
+		/** @var list<string> $userIds */
+		$userIds = [];
+		/** @psalm-suppress MixedAssignment - IResult::fetch() returns mixed */
+		while (($row = $result->fetch()) !== false) {
+			if (is_array($row) && isset($row['userid']) && is_string($row['userid'])) {
+				$userIds[] = $row['userid'];
+			}
+		}
+		$result->closeCursor();
+
+		return $userIds;
+	}
+
 	/**
 	 * Get the access token for a user, handling expiration and refresh.
 	 *