feat: allow TLS connections with invalid certificate if the key is unchanged

src/context.rs

@@ -25,7 +25,7 @@ use crate::key::self_fingerprint;
 use crate::log::warn;
 use crate::logged_debug_assert;
 use crate::message::{self, MessageState, MsgId};
-use crate::net::tls::TlsSessionStore;
+use crate::net::tls::{SpkiHashStore, TlsSessionStore};
 use crate::peer_channels::Iroh;
 use crate::push::PushSubscriber;
 use crate::quota::QuotaInfo;
@@ -308,6 +308,13 @@ pub struct InnerContext {
     /// TLS session resumption cache.
     pub(crate) tls_session_store: TlsSessionStore,
 
+    /// Store for TLS SPKI hashes.
+    ///
+    /// Used to remember public keys
+    /// of TLS certificates to accept them
+    /// even after they expire.
+    pub(crate) spki_hash_store: SpkiHashStore,
+
     /// Iroh for realtime peer channels.
     pub(crate) iroh: Arc<RwLock<Option<Iroh>>>,
 
@@ -511,6 +518,7 @@ impl Context {
             push_subscriber,
             push_subscribed: AtomicBool::new(false),
             tls_session_store: TlsSessionStore::new(),
+            spki_hash_store: SpkiHashStore::new(),
             iroh: Arc::new(RwLock::new(None)),
             self_fingerprint: OnceLock::new(),
             self_public_key: Mutex::new(None),

src/imap/client.rs

@@ -220,6 +220,8 @@ impl Client {
             alpn(addr.port()),
             logging_stream,
             &context.tls_session_store,
+            &context.spki_hash_store,
+            &context.sql,
         )
         .await?;
         let buffered_stream = BufWriter::new(tls_stream);
@@ -282,6 +284,8 @@ impl Client {
             "",
             tcp_stream,
             &context.tls_session_store,
+            &context.spki_hash_store,
+            &context.sql,
         )
         .await
         .context("STARTTLS upgrade failed")?;
@@ -310,6 +314,8 @@ impl Client {
             alpn(port),
             proxy_stream,
             &context.tls_session_store,
+            &context.spki_hash_store,
+            &context.sql,
         )
         .await?;
         let buffered_stream = BufWriter::new(tls_stream);
@@ -373,6 +379,8 @@ impl Client {
             "",
             proxy_stream,
             &context.tls_session_store,
+            &context.spki_hash_store,
+            &context.sql,
         )
         .await
         .context("STARTTLS upgrade failed")?;

src/net.rs

@@ -12,7 +12,7 @@ use tokio_io_timeout::TimeoutStream;
 
 use crate::context::Context;
 use crate::net::session::SessionStream;
-use crate::net::tls::TlsSessionStore;
+use crate::net::tls::{SpkiHashStore, TlsSessionStore};
 use crate::sql::Sql;
 use crate::tools::time;
 
@@ -130,6 +130,8 @@ pub(crate) async fn connect_tls_inner(
     strict_tls: bool,
     alpn: &str,
     tls_session_store: &TlsSessionStore,
+    spki_hash_store: &SpkiHashStore,
+    sql: &Sql,
 ) -> Result<impl SessionStream + 'static> {
     let use_sni = true;
     let tcp_stream = connect_tcp_inner(addr).await?;
@@ -141,6 +143,8 @@ pub(crate) async fn connect_tls_inner(
         alpn,
         tcp_stream,
         tls_session_store,
+        spki_hash_store,
+        sql,
     )
     .await?;
     Ok(tls_stream)

src/net/http.rs

@@ -87,6 +87,8 @@ where
                     "",
                     proxy_stream,
                     &context.tls_session_store,
+                    &context.spki_hash_store,
+                    &context.sql,
                 )
                 .await?;
                 Box::new(tls_stream)
@@ -99,6 +101,8 @@ where
                     "",
                     tcp_stream,
                     &context.tls_session_store,
+                    &context.spki_hash_store,
+                    &context.sql,
                 )
                 .await?;
                 Box::new(tls_stream)

src/net/proxy.rs

@@ -436,6 +436,8 @@ impl ProxyConfig {
                     "",
                     tcp_stream,
                     &context.tls_session_store,
+                    &context.spki_hash_store,
+                    &context.sql,
                 )
                 .await?;
                 let auth = if let Some((username, password)) = &https_config.user_password {

src/net/tls.rs

@@ -6,13 +6,20 @@ use std::sync::Arc;
 use anyhow::Result;
 
 use crate::net::session::SessionStream;
+use crate::sql::Sql;
+use crate::tools::time;
 
 use tokio_rustls::rustls;
 use tokio_rustls::rustls::client::ClientSessionStore;
+use tokio_rustls::rustls::server::ParsedCertificate;
 
 mod danger;
-use danger::NoCertificateVerification;
+use danger::CustomCertificateVerifier;
 
+mod spki;
+pub use spki::SpkiHashStore;
+
+#[expect(clippy::too_many_arguments)]
 pub async fn wrap_tls<'a>(
     strict_tls: bool,
     hostname: &str,
@@ -21,10 +28,21 @@ pub async fn wrap_tls<'a>(
     alpn: &str,
     stream: impl SessionStream + 'static,
     tls_session_store: &TlsSessionStore,
+    spki_hash_store: &SpkiHashStore,
+    sql: &Sql,
 ) -> Result<impl SessionStream + 'a> {
     if strict_tls {
-        let tls_stream =
-            wrap_rustls(hostname, port, use_sni, alpn, stream, tls_session_store).await?;
+        let tls_stream = wrap_rustls(
+            hostname,
+            port,
+            use_sni,
+            alpn,
+            stream,
+            tls_session_store,
+            spki_hash_store,
+            sql,
+        )
+        .await?;
         let boxed_stream: Box<dyn SessionStream> = Box::new(tls_stream);
         Ok(boxed_stream)
     } else {
@@ -94,16 +112,19 @@ impl TlsSessionStore {
     }
 }
 
+#[expect(clippy::too_many_arguments)]
 pub async fn wrap_rustls<'a>(
     hostname: &str,
     port: u16,
     use_sni: bool,
     alpn: &str,
     stream: impl SessionStream + 'a,
     tls_session_store: &TlsSessionStore,
+    spki_hash_store: &SpkiHashStore,
+    sql: &Sql,
 ) -> Result<impl SessionStream + 'a> {
-    let mut root_cert_store = rustls::RootCertStore::empty();
-    root_cert_store.extend(webpki_roots::TLS_SERVER_ROOTS.iter().cloned());
+    let root_cert_store =
+        rustls::RootCertStore::from_iter(webpki_roots::TLS_SERVER_ROOTS.iter().cloned());
 
     let mut config = rustls::ClientConfig::builder()
         .with_root_certificates(root_cert_store)
@@ -127,20 +148,28 @@ pub async fn wrap_rustls<'a>(
     config.resumption = resumption;
     config.enable_sni = use_sni;
 
-    // Do not verify certificates for hostnames starting with `_`.
-    // They are used for servers with self-signed certificates, e.g. for local testing.
-    // Hostnames starting with `_` can have only self-signed TLS certificates or wildcard certificates.
-    // It is not possible to get valid non-wildcard TLS certificates because CA/Browser Forum requirements
-    // explicitly state that domains should start with a letter, digit or hyphen:
-    // https://github.com/cabforum/servercert/blob/24f38fd4765e019db8bb1a8c56bf63c7115ce0b0/docs/BR.md
-    if hostname.starts_with("_") {
-        config
-            .dangerous()
-            .set_certificate_verifier(Arc::new(NoCertificateVerification::new()));
-    }
+    config
+        .dangerous()
+        .set_certificate_verifier(Arc::new(CustomCertificateVerifier::new(
+            spki_hash_store.get_spki_hash(hostname, sql).await?,
+        )));
 
     let tls = tokio_rustls::TlsConnector::from(Arc::new(config));
     let name = tokio_rustls::rustls::pki_types::ServerName::try_from(hostname)?.to_owned();
     let tls_stream = tls.connect(name, stream).await?;
+
+    // Successfully connected.
+    // Remember SPKI hash to accept it later if certificate expires.
+    let (_io, client_connection) = tls_stream.get_ref();
+    if let Some(end_entity) = client_connection
+        .peer_certificates()
+        .and_then(|certs| certs.first())
+    {
+        let now = time();
+        let parsed_certificate = ParsedCertificate::try_from(end_entity)?;
+        let spki = parsed_certificate.subject_public_key_info();
+        spki_hash_store.save_spki(hostname, &spki, sql, now).await?;
+    }
+
     Ok(tls_stream)
 }

src/net/tls/danger.rs

@@ -1,26 +1,93 @@
-//! Dangerous TLS implementation of accepting invalid certificates for Rustls.
+//! Custom TLS verification.
+//!
+//! We want to accept expired certificates.
 
+use rustls::RootCertStore;
+use rustls::client::{verify_server_cert_signed_by_trust_anchor, verify_server_name};
 use rustls::pki_types::{CertificateDer, ServerName, UnixTime};
+use rustls::server::ParsedCertificate;
 use tokio_rustls::rustls;
 
+use crate::net::tls::spki::spki_hash;
+
 #[derive(Debug)]
-pub(super) struct NoCertificateVerification();
+pub(super) struct CustomCertificateVerifier {
+    /// Root certificates.
+    root_cert_store: RootCertStore,
+
+    /// Expected SPKI hash as a base64 of SHA-256.
+    spki_hash: Option<String>,
+}
 
-impl NoCertificateVerification {
-    pub(super) fn new() -> Self {
-        Self()
+impl CustomCertificateVerifier {
+    pub(super) fn new(spki_hash: Option<String>) -> Self {
+        let root_cert_store =
+            RootCertStore::from_iter(webpki_roots::TLS_SERVER_ROOTS.iter().cloned());
+        Self {
+            root_cert_store,
+            spki_hash,
+        }
     }
 }
 
-impl rustls::client::danger::ServerCertVerifier for NoCertificateVerification {
+impl rustls::client::danger::ServerCertVerifier for CustomCertificateVerifier {
     fn verify_server_cert(
         &self,
-        _end_entity: &CertificateDer<'_>,
-        _intermediates: &[CertificateDer<'_>],
-        _server_name: &ServerName<'_>,
+        end_entity: &CertificateDer<'_>,
+        intermediates: &[CertificateDer<'_>],
+        server_name: &ServerName<'_>,
+        // OCSP is a certificate revocation mechanism that is intentionally ignored.
+        // It is practically not used and is essentially deprecated
+        // in favor of Certificate Revocation Lists.
+        // Let's Encrypt has disabled OCSP responders in 2025:
+        // <https://letsencrypt.org/2025/08/06/ocsp-service-has-reached-end-of-life>.
+        // Theoretically checking of stapled OCSP responses could be implemented,
+        // but it is not interesting to implement it because it is not used
+        // by the servers: <https://github.com/rustls/webpki/issues/217>.
         _ocsp_response: &[u8],
-        _now: UnixTime,
+        now: UnixTime,
     ) -> Result<rustls::client::danger::ServerCertVerified, rustls::Error> {
+        let parsed_certificate = ParsedCertificate::try_from(end_entity)?;
+
+        let spki = parsed_certificate.subject_public_key_info();
+
+        let provider = rustls::crypto::ring::default_provider();
+
+        if let ServerName::DnsName(dns_name) = server_name
+            && dns_name.as_ref().starts_with("_")
+        {
+            // Do not verify certificates for hostnames starting with `_`.
+            // They are used for servers with self-signed certificates, e.g. for local testing.
+            // Hostnames starting with `_` can have only self-signed TLS certificates or wildcard certificates.
+            // It is not possible to get valid non-wildcard TLS certificates because CA/Browser Forum requirements
+            // explicitly state that domains should start with a letter, digit or hyphen:
+            // https://github.com/cabforum/servercert/blob/24f38fd4765e019db8bb1a8c56bf63c7115ce0b0/docs/BR.md
+        } else if let Some(hash) = &self.spki_hash
+            && spki_hash(&spki) == *hash
+        {
+            // Last time we successfully connected to this hostname with TLS checks,
+            // SPKI had this hash.
+            // It does not matter if certificate has now expired.
+        } else {
+            // verify_server_cert_signed_by_trust_anchor does no revocation checking:
+            // <https://docs.rs/rustls/0.23.37/rustls/client/fn.verify_server_cert_signed_by_trust_anchor.html>
+            // We don't do it either.
+            verify_server_cert_signed_by_trust_anchor(
+                &parsed_certificate,
+                &self.root_cert_store,
+                intermediates,
+                now,
+                provider.signature_verification_algorithms.all,
+            )?;
+        }
+
+        // Verify server name unconditionally.
+        //
+        // We do this even for self-signed certificates when hostname starts with `_`
+        // so we don't try to connect to captive portals
+        // and fail on MITM certificates if they are generated once
+        // and reused for all hostnames.
+        verify_server_name(&parsed_certificate, server_name)?;
         Ok(rustls::client::danger::ServerCertVerified::assertion())
     }