Trace agent connection phases without long-lived entered spans

docs/telemetry.md

@@ -94,6 +94,12 @@ existing debug events too; inspect them before enabling it broadly.
   and wake dispatch. Counts distinguish grouped, filtered, and returned rows;
   wake events identify the chosen agent and whether the route was explicit,
   without recording device identifiers or addresses.
+- Connectivity uses short `agent_dns`, `agent_connect`, `agent_handshake_send`,
+  and CC `agent_auth_verify` spans, rather than connection-long spans. Connect
+  attempts also contribute to operation metrics. Lifecycle events report retries
+  with backoff and CC disconnect duration. Sending credentials is not an auth ACK;
+  CC's authentication event is the authoritative result. DNS diagnostics are a
+  separate lookup, not a measurement of the resolver inside WebSocket connect.
 
 Instrument operation boundaries rather than individual rows or terminal chunks.
 Use `skip_all`, explicitly allow count fields, and instrument async futures rather

wakey-agent/src/session.rs

@@ -4,7 +4,7 @@ use std::net::IpAddr;
 use std::time::Instant;
 use tokio::time::{Duration, MissedTickBehavior, interval, sleep};
 use tokio_tungstenite::{connect_async, tungstenite::Message};
-use tracing::{debug, error, info, info_span, warn};
+use tracing::{Instrument, debug, error, info, info_span, warn};
 
 use crate::config::AgentConfig;
 use crate::dispatch::{dispatch_command, inventory_for_config};
@@ -25,7 +25,7 @@ pub async fn run(config: AgentConfig) -> Result<()> {
                 backoff = config.reconnect_base_ms.max(100);
             }
             Err(err) => {
-                warn!(error = %err, backoff_ms = backoff, "agent session ended; reconnecting");
+                warn!(agent_id = %config.agent_id, error = %err, backoff_ms = backoff, "agent session ended; reconnecting");
                 sleep(Duration::from_millis(backoff)).await;
                 backoff = next_backoff_ms(backoff, config.reconnect_max_ms);
             }
@@ -40,20 +40,14 @@ async fn run_once(
         crate::terminal::TerminalManagerEvent,
     >,
 ) -> Result<()> {
-    let session_id = format!(
+    // Connection-long spans export too late and entered guards are unsafe across
-        "{}-{}",
+    // awaits. Short phase spans export while a healthy socket is still running.
-        std::process::id(),
-        std::time::SystemTime::now()
-            .duration_since(std::time::UNIX_EPOCH)
-            .map(|d| d.as_millis())
-            .unwrap_or_default()
-    );
-    let span = info_span!("agent_session", session_id = %session_id, agent_id = %config.agent_id);
-    let _span_guard = span.enter(); // the ENTIRETY of below is agent_session.
-
     let ws_url = websocket_url(&config.server_url)?;
     info!(%ws_url, agent_id = %config.agent_id, "connecting agent websocket");
-    if let Some((dns_resolve_ms, resolved_addrs)) = dns_resolution_diagnostics(&ws_url).await {
+    if let Some((dns_resolve_ms, resolved_addrs)) = dns_resolution_diagnostics(&ws_url)
+        .instrument(info_span!("agent_dns", agent_id = %config.agent_id))
+        .await
+    {
         info!(
             host = %ws_url.host_str().unwrap_or(""),
             dns_resolve_ms,
@@ -70,7 +64,15 @@ async fn run_once(
         }
     }
     let connect_started = Instant::now();
-    let (stream, _) = connect_async(ws_url.as_str())
+    let (stream, _) = async {
+        let mut operation = wakey_core::telemetry::Operation::new("agent_connect");
+        let result = connect_async(ws_url.as_str()).await;
+        if result.is_ok() {
+            operation.outcome("ok");
+        }
+        result
+    }
+    .instrument(info_span!("agent_connect", agent_id = %config.agent_id))
     .await
     .context("failed to connect websocket")?;
     let ws_connect_ms = connect_started.elapsed().as_millis() as u64;
@@ -80,6 +82,7 @@ async fn run_once(
     }
     let (mut sink, mut source) = stream.split();
 
+    async {
         send_json(
             &mut sink,
             &ClientMessage::Hello {
@@ -106,7 +109,11 @@ async fn run_once(
         )
         .await?;
         send_terminal_sessions(&mut sink, terminal_manager).await?;
-    info!(agent_id = %config.agent_id, "agent websocket session authenticated");
+        Ok::<_, anyhow::Error>(())
+    }
+    .instrument(info_span!("agent_handshake_send", agent_id = %config.agent_id))
+    .await?;
+    info!(agent_id = %config.agent_id, "agent hello and credentials sent; awaiting server traffic");
 
     let mut heartbeat = interval(Duration::from_secs(30));
     heartbeat.set_missed_tick_behavior(MissedTickBehavior::Skip);

wakey-control-plane/src/ws.rs

@@ -6,7 +6,7 @@ use futures_util::{SinkExt, StreamExt};
 use serde::Deserialize;
 use std::time::Instant;
 use tokio::sync::mpsc;
-use tracing::{debug, info, info_span, warn};
+use tracing::{Instrument, debug, info, info_span, warn};
 use uuid::Uuid;
 use wakey_agent::protocol::{
     AgentCapability, AgentCapabilityOptions, AgentTerminalSession, DEFAULT_TERMINAL_MAX_SESSIONS,
@@ -71,9 +71,9 @@ pub async fn agent_ws(ws: WebSocketUpgrade, State(state): State<AppState>) -> im
 
 async fn handle_agent_socket(state: AppState, socket: WebSocket) {
     let connection_id = Uuid::new_v4().to_string();
-    let span = info_span!("agent_ws_connection", connection_id = %connection_id);
+    // Lifecycle events are available immediately; do not hold an entered span
-    let _span_guard = span.enter();
+    // across socket awaits or wait for disconnect to export the connection.
-    info!("agent websocket upgraded");
+    info!(%connection_id, "agent websocket upgraded");
     let connected_at = Instant::now();
 
     let (mut write, mut read) = socket.split();
@@ -111,11 +111,11 @@ async fn handle_agent_socket(state: AppState, socket: WebSocket) {
         let msg = match frame {
             Some(Ok(msg)) => msg,
             Some(Err(err)) => {
-                warn!(error = %err, "agent websocket receive error");
+                warn!(%connection_id, error = %err, "agent websocket receive error");
                 break;
             }
             None => {
-                info!("agent websocket stream ended by peer");
+                info!(%connection_id, "agent websocket stream ended by peer");
                 break;
             }
         };
@@ -132,14 +132,14 @@ async fn handle_agent_socket(state: AppState, socket: WebSocket) {
                 )
                 .await
                 {
-                    warn!(error = %err, "closing agent websocket due to protocol/auth error");
+                    warn!(%connection_id, error = %err, "closing agent websocket due to protocol/auth error");
                     break;
                 }
             }
             Message::Ping(_) => {}
             Message::Pong(_) => {}
             Message::Close(frame) => {
-                info!(close = ?frame, "agent websocket close frame received");
+                info!(%connection_id, close = ?frame, "agent websocket close frame received");
                 break;
             }
             Message::Binary(_) => {
@@ -149,7 +149,7 @@ async fn handle_agent_socket(state: AppState, socket: WebSocket) {
     }
 
     if let Some(agent_id) = connection.authed_agent_id {
-        info!(agent_id = %agent_id, "agent disconnected");
+        info!(%connection_id, agent_id = %agent_id, connected_ms = now_duration_ms(connected_at.elapsed()), "agent disconnected");
         let mut sessions = state.sessions.write().await;
         let should_remove = sessions
             .get(&agent_id)
@@ -245,6 +245,7 @@ async fn process_agent_text(
             if !state
                 .store
                 .verify_agent_token(&agent_id, &agent_token)
+                .instrument(info_span!("agent_auth_verify", agent_id = %agent_id, %connection_id))
                 .await
             {
                 warn!(agent_id = %agent_id, "agent auth rejected");