fix: add wall-clock certificate expiry check to webhook TLS rotation

crates/stackable-webhook/src/tls/cert_resolver.rs

@@ -1,4 +1,4 @@
-use std::sync::Arc;
+use std::{sync::Arc, time::SystemTime};
 
 use arc_swap::ArcSwap;
 use snafu::{OptionExt, ResultExt, Snafu};
@@ -57,6 +57,9 @@ pub struct CertificateResolver {
     /// Using a [`ArcSwap`] (over e.g. [`tokio::sync::RwLock`]), so that we can easily
     /// (and performant) bridge between async write and sync read.
     current_certified_key: ArcSwap<CertifiedKey>,
+    /// The wall-clock expiry time (`not_after`) of the current certificate.
+    /// Used to detect clock drift between monotonic and wall-clock time.
+    current_not_after: ArcSwap<SystemTime>,
     subject_alterative_dns_names: Arc<Vec<String>>,
 
     certificate_tx: mpsc::Sender<Certificate>,
@@ -68,7 +71,7 @@ impl CertificateResolver {
         certificate_tx: mpsc::Sender<Certificate>,
     ) -> Result<Self> {
         let subject_alterative_dns_names = Arc::new(subject_alterative_dns_names);
-        let certified_key = Self::generate_new_certificate_inner(
+        let (certified_key, not_after) = Self::generate_new_certificate_inner(
             subject_alterative_dns_names.clone(),
             &certificate_tx,
         )
@@ -77,20 +80,37 @@ impl CertificateResolver {
         Ok(Self {
             subject_alterative_dns_names,
             current_certified_key: ArcSwap::new(certified_key),
+            current_not_after: ArcSwap::new(Arc::new(not_after)),
             certificate_tx,
         })
     }
 
     pub async fn rotate_certificate(&self) -> Result<()> {
-        let certified_key = self.generate_new_certificate().await?;
+        let (certified_key, not_after) = self.generate_new_certificate().await?;
 
         // TODO: Sign the new cert somehow with the old cert. See https://github.com/stackabletech/decisions/issues/56
         self.current_certified_key.store(certified_key);
+        self.current_not_after.store(Arc::new(not_after));
 
         Ok(())
     }
 
-    async fn generate_new_certificate(&self) -> Result<Arc<CertifiedKey>> {
+    /// Returns `true` if the current certificate is expired or will expire
+    /// within the given `buffer` duration according to wall-clock time.
+    ///
+    /// This catches cases where the monotonic timer (used by `tokio::time`)
+    /// has drifted from wall-clock time, e.g. due to system hibernation.
+    pub fn needs_rotation(&self, buffer: std::time::Duration) -> bool {
+        let not_after = **self.current_not_after.load();
+        // If subtraction underflows (buffer > time since epoch), fall back to
+        // UNIX_EPOCH so that the comparison always triggers rotation.
+        let deadline = not_after
+            .checked_sub(buffer)
+            .unwrap_or(SystemTime::UNIX_EPOCH);
+        SystemTime::now() >= deadline
+    }
+
+    async fn generate_new_certificate(&self) -> Result<(Arc<CertifiedKey>, SystemTime)> {
         let subject_alterative_dns_names = self.subject_alterative_dns_names.clone();
         Self::generate_new_certificate_inner(subject_alterative_dns_names, &self.certificate_tx)
             .await
@@ -106,7 +126,7 @@ impl CertificateResolver {
     async fn generate_new_certificate_inner(
         subject_alterative_dns_names: Arc<Vec<String>>,
         certificate_tx: &mpsc::Sender<Certificate>,
-    ) -> Result<Arc<CertifiedKey>> {
+    ) -> Result<(Arc<CertifiedKey>, SystemTime)> {
         // The certificate generations can take a while, so we use `spawn_blocking`
         let (cert, certified_key) = tokio::task::spawn_blocking(move || {
             let tls_provider =
@@ -144,12 +164,14 @@ impl CertificateResolver {
         .await
         .context(TokioSpawnBlockingSnafu)??;
 
+        let not_after = cert.tbs_certificate.validity.not_after.to_system_time();
+
         certificate_tx
             .send(cert)
             .await
             .map_err(|_err| CertificateResolverError::SendCertificateToChannel)?;
 
-        Ok(certified_key)
+        Ok((certified_key, not_after))
     }
 }
 

crates/stackable-webhook/src/tls/mod.rs

@@ -39,8 +39,25 @@ use crate::{
 mod cert_resolver;
 
 pub const WEBHOOK_CA_LIFETIME: Duration = Duration::from_hours_unchecked(24);
-pub const WEBHOOK_CERTIFICATE_LIFETIME: Duration = Duration::from_hours_unchecked(24);
-pub const WEBHOOK_CERTIFICATE_ROTATION_INTERVAL: Duration = Duration::from_hours_unchecked(20);
+
+/// The wall-clock lifetime of generated webhook certificates. If this is ever
+/// reduced, ensure it stays well above [`CERTIFICATE_ROTATION_CHECK_INTERVAL`]
+/// (currently 5 minutes), otherwise the certificate could expire between checks.
+const WEBHOOK_CERTIFICATE_LIFETIME_HOURS: u64 = 24;
+pub const WEBHOOK_CERTIFICATE_LIFETIME: Duration =
+    Duration::from_hours_unchecked(WEBHOOK_CERTIFICATE_LIFETIME_HOURS);
+
+/// How often to check whether the certificate needs rotation. This is
+/// intentionally independent of the certificate lifetime — it controls how
+/// quickly we detect wall-clock drift (from hibernation, VM migration, etc.),
+/// not how long the certificate lives.
+const CERTIFICATE_ROTATION_CHECK_INTERVAL: Duration = Duration::from_minutes_unchecked(5);
+
+/// Rotate the certificate when less than 1/6 of its lifetime remains
+/// (4 hours for the current 24h lifetime). Derived from
+/// [`WEBHOOK_CERTIFICATE_LIFETIME`] so it scales if the lifetime changes.
+const CERTIFICATE_EXPIRY_BUFFER: Duration =
+    Duration::from_minutes_unchecked(WEBHOOK_CERTIFICATE_LIFETIME_HOURS * 60 / 6);
 
 pub type Result<T, E = TlsServerError> = std::result::Result<T, E>;
 
@@ -153,8 +170,12 @@ impl TlsServer {
             router,
         } = self;
 
-        let start = tokio::time::Instant::now() + *WEBHOOK_CERTIFICATE_ROTATION_INTERVAL;
-        let mut interval = tokio::time::interval_at(start, *WEBHOOK_CERTIFICATE_ROTATION_INTERVAL);
+        // Periodically check whether the certificate needs rotation based on
+        // wall-clock time. This avoids the monotonic vs wall-clock drift problem
+        // that can occur during hibernation, VM migration, or cgroup freezing.
+        let check_start = tokio::time::Instant::now() + *CERTIFICATE_ROTATION_CHECK_INTERVAL;
+        let mut rotation_check =
+            tokio::time::interval_at(check_start, *CERTIFICATE_ROTATION_CHECK_INTERVAL);
 
         let tls_acceptor = TlsAcceptor::from(Arc::new(config));
         let tcp_listener = TcpListener::bind(socket_addr)
@@ -183,11 +204,10 @@ impl TlsServer {
         loop {
             let tls_acceptor = tls_acceptor.clone();
 
-            // Wait for either a new TCP connection or the certificate rotation interval tick
             tokio::select! {
                 // We opt for a biased execution of arms to make sure we always check if a
-                // shutdown signal was received or the certificate needs rotation based on the
-                // interval. This ensures, we always use a valid certificate for the TLS connection.
+                // shutdown signal was received or the certificate needs rotation before
+                // accepting new connections.
                 biased;
 
                 // Once a shutdown signal is received (this future becomes `Poll::Ready`), break out
@@ -198,13 +218,16 @@ impl TlsServer {
                     break;
                 }
 
-                // This is cancellation-safe. If this branch is cancelled, the tick is NOT consumed.
-                // As such, we will not miss rotating the certificate.
-                _ = interval.tick() => {
-                    cert_resolver
-                        .rotate_certificate()
-                        .await
-                        .context(RotateCertificateSnafu)?
+                // Check wall-clock time to decide if the certificate needs rotation.
+                // This is cancellation-safe: if cancelled, the tick is NOT consumed.
+                _ = rotation_check.tick() => {
+                    if cert_resolver.needs_rotation(*CERTIFICATE_EXPIRY_BUFFER) {
+                        tracing::info!("certificate approaching expiry, rotating");
+                        cert_resolver
+                            .rotate_certificate()
+                            .await
+                            .context(RotateCertificateSnafu)?;
+                    }
                 }
 
                 // This is cancellation-safe. If cancelled, no new connections are accepted.