fix(agent): SPEC-018 Phase 1 review fixes (cancellable session loop, panic guard, service-create retry)

H: thread the SCM cooperative-stop flag into the connected session loop
(run_with_tray) via a new Option<&Arc<AtomicBool>> param. The flag was only
observed by the outer run_agent reconnect loop, which never runs while a
session is connected, so an SCM Stop/Shutdown left the service Running until
force-kill. The inner loop now checks it each tick, closes the WS cleanly, and
returns the SERVICE_STOP sentinel that the outer loop maps to a graceful stop.
The new param is optional: attended/viewer/interactive callers pass None and
behave exactly as before.

M: wrap the managed-agent runtime block_on in catch_unwind(AssertUnwindSafe) so
a panic in the agent future cannot unwind across the extern "system" service
entry (UB/abort). A caught panic becomes an Err -> ServiceExitCode::ServiceSpecific(1)
so SCM recovery engages cleanly.

L1: replace the fixed 2s sleep after delete() on reinstall with a bounded retry
on CreateService returning ERROR_SERVICE_MARKED_FOR_DELETE (1072), gated on
having actually deleted a prior instance.

L2: clarify the --elevated -> force_user_install mapping (comment only).

N1: add a clap-metadata test pinning the service-run subcommand name to
SERVICE_RUN_ARG, cross-linked from the existing literal test.

N2: correct the service doc comments now that graceful stop interrupts the
connected case too.

Verified on Windows host: cargo fmt --check, clippy -D warnings, release build
(x86_64-pc-windows-msvc), and cargo test (58 passed) all green.

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

agent/src/main.rs

@@ -234,7 +234,24 @@ fn main() -> Result<()> {
         Some(Commands::Install {
             user_only,
             elevated,
-        }) => run_install(user_only || elevated),
+        }) => {
+            // `run_install`'s parameter is `force_user_install` — when true it
+            // skips the UAC re-elevation attempt and installs in-place with
+            // whatever rights this process already has.
+            //
+            // - `user_only`: the user explicitly asked for a per-user install;
+            //   honour it directly.
+            // - `elevated`: this is the internal, already-elevated re-exec spawned
+            //   by `try_elevate_and_install` ("install --elevated"). It must NOT
+            //   attempt to elevate AGAIN (that would loop / re-prompt), so we pass
+            //   force=true here too. This is correct even though it routes through
+            //   the "user install" parameter, because the re-exec genuinely runs
+            //   elevated: `is_elevated()` returns true inside `install()`, so the
+            //   path resolves to Program Files and the LocalSystem service installs
+            //   normally. The flag only suppresses re-elevation; it does not force a
+            //   per-user (non-elevated) install when we are already elevated.
+            run_install(user_only || elevated)
+        }
         Some(Commands::Uninstall) => run_uninstall(),
         Some(Commands::Launch { url }) => run_launch(&url),
         Some(Commands::VersionInfo) => {
@@ -413,14 +430,40 @@ pub fn run_managed_agent_service(
     }
 
     let rt = tokio::runtime::Runtime::new()?;
-    rt.block_on(async move {
+
-        // SPEC-016 Phase B: resolve the operating credential before connecting.
+    // SPEC-018 (finding M): this future runs across the `extern "system"` service
-        // Running as SYSTEM, the SYSTEM+Administrators-ACL'd cak_ store is now
+    // entry point (ffi_service_main -> service_main -> run_service -> here). A
-        // readable in-context, so the Phase B fail-fast guard is not hit on this
+    // panic that unwound across that FFI boundary is undefined behaviour (the C
-        // path (it remains as a safety net for any non-SYSTEM invocation).
+    // ABI cannot carry a Rust unwind) and would abort the process instead of
-        resolve_agent_credential(&mut config).await?;
+    // taking the intended ServiceSpecific(1) fault path. Catch it here and convert
-        run_agent(config, Some(shutdown)).await
+    // it into an `Err`, which `run_service` maps to ServiceExitCode::ServiceSpecific(1)
-    })
+    // so the SCM applies its configured recovery (restart) cleanly. `Running` is
+    // already reported before we get here, so a fault does not strand StartPending.
+    let outcome = std::panic::catch_unwind(std::panic::AssertUnwindSafe(|| {
+        rt.block_on(async move {
+            // SPEC-016 Phase B: resolve the operating credential before connecting.
+            // Running as SYSTEM, the SYSTEM+Administrators-ACL'd cak_ store is now
+            // readable in-context, so the Phase B fail-fast guard is not hit on this
+            // path (it remains as a safety net for any non-SYSTEM invocation).
+            resolve_agent_credential(&mut config).await?;
+            run_agent(config, Some(shutdown)).await
+        })
+    }));
+
+    match outcome {
+        Ok(result) => result,
+        Err(panic) => {
+            // Recover a human-readable message from the panic payload for the log;
+            // do not re-panic (that would unwind across the FFI boundary again).
+            let detail = panic
+                .downcast_ref::<&str>()
+                .map(|s| s.to_string())
+                .or_else(|| panic.downcast_ref::<String>().cloned())
+                .unwrap_or_else(|| "non-string panic payload".to_string());
+            error!("managed-agent runtime panicked: {detail}");
+            Err(anyhow::anyhow!("managed-agent runtime panicked: {detail}"))
+        }
+    }
 }
 
 /// SPEC-018 Phase 1: handle an interactive launch of a MANAGED agent binary (one
@@ -812,11 +855,22 @@ async fn run_agent(
                 }
 
                 if let Err(e) = session
-                    .run_with_tray(tray.as_ref(), chat_ctrl.as_ref())
+                    .run_with_tray(tray.as_ref(), chat_ctrl.as_ref(), service_shutdown.as_ref())
                     .await
                 {
                     let error_msg = e.to_string();
 
+                    // SPEC-018 (finding H): the connected session loop broke
+                    // because the SCM asked the service to stop. The loop already
+                    // closed the WebSocket cleanly; treat this as a graceful stop
+                    // (no reconnect) so the service transitions StopPending ->
+                    // Stopped. Only the service path can produce this (it is the
+                    // only caller that passes a shutdown flag).
+                    if error_msg.contains(session::SERVICE_STOP_SENTINEL) {
+                        info!("Service stop requested during session; exiting agent loop");
+                        return Ok(());
+                    }
+
                     if error_msg.contains("USER_EXIT") {
                         info!("Session ended by user");
                         cleanup_on_exit();
@@ -904,3 +958,32 @@ async fn run_agent(
         }
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use clap::CommandFactory;
+
+    /// SPEC-018 finding N1: pin the clap subcommand name to the constant the SCM
+    /// is registered with. The service is installed with `SERVICE_RUN_ARG` as its
+    /// launch argument; when the SCM starts it, clap must route that exact token
+    /// into [`Commands::ServiceRun`]. If the `#[command(name = "service-run")]`
+    /// attribute and the constant ever drift apart, the SCM would start the binary
+    /// but clap would fail to match the subcommand and the process would fall
+    /// through to default (non-service) mode and exit. Asserting against the live
+    /// clap metadata (not a second string literal) makes that drift impossible.
+    #[test]
+    #[cfg(windows)]
+    fn service_run_subcommand_matches_scm_launch_arg() {
+        let cmd = Cli::command();
+        let has_matching_subcommand = cmd
+            .get_subcommands()
+            .any(|sc| sc.get_name() == service::SERVICE_RUN_ARG);
+        assert!(
+            has_matching_subcommand,
+            "no clap subcommand named '{}' (the SCM launch arg); the ServiceRun \
+             #[command(name = ...)] attribute drifted from service::SERVICE_RUN_ARG",
+            service::SERVICE_RUN_ARG
+        );
+    }
+}

agent/src/service/mod.rs

@@ -12,7 +12,11 @@
 //!      relay WSS connection.
 //!   2. Report a correct service lifecycle to the SCM (`StartPending` ->
 //!      `Running` -> `StopPending` -> `Stopped`) and handle `Stop`/`Shutdown`
-//!      gracefully (signal the agent loop to close the WS connection and exit).
+//!      gracefully. The control handler sets a shared shutdown flag; the agent
+//!      runtime observes it both between reconnect attempts AND inside the
+//!      connected session loop (SPEC-018 finding H), so a stop received while a
+//!      session is live breaks out promptly, closes the WS connection cleanly,
+//!      and exits — rather than waiting for the SCM to force-kill.
 //!   3. Provide install/uninstall of the service (LocalSystem, auto-start, crash
 //!      recovery) so managed mode uses the service as its single autostart
 //!      instead of the per-user `HKCU\…\Run` entry.
@@ -122,6 +126,11 @@ fn run_service() -> Result<()> {
             // we intentionally do not accept SESSIONCHANGE yet.
             ServiceControl::Stop | ServiceControl::Shutdown => {
                 info!("received {control_event:?}; signalling agent to shut down");
+                // Set the cooperative-stop flag. The agent runtime observes it on
+                // every idle tick of the connected session loop and between
+                // reconnect attempts (SPEC-018 finding H), so it breaks out and
+                // closes the WebSocket cleanly within ~100ms even if a session is
+                // currently connected.
                 shutdown_for_handler.store(true, Ordering::SeqCst);
                 ServiceControlHandlerResult::NoError
             }
@@ -253,6 +262,7 @@ pub fn install_service(exe_path: &std::path::Path) -> Result<()> {
     .context("failed to connect to the Service Control Manager (run as Administrator)")?;
 
     // Remove any prior installation so the binary path / args are refreshed.
+    let mut deleted_existing = false;
     if let Ok(existing) = manager.open_service(
         SERVICE_NAME,
         ServiceAccess::QUERY_STATUS | ServiceAccess::STOP | ServiceAccess::DELETE,
@@ -263,9 +273,7 @@ pub fn install_service(exe_path: &std::path::Path) -> Result<()> {
             .delete()
             .context("failed to delete the existing service before reinstall")?;
         drop(existing);
-        // The SCM marks a service for deletion but only removes it once all handles
+        deleted_existing = true;
-        // close; a brief settle avoids a CreateService "marked for deletion" race.
-        std::thread::sleep(Duration::from_secs(2));
     }
 
     let service_info = ServiceInfo {
@@ -282,8 +290,7 @@ pub fn install_service(exe_path: &std::path::Path) -> Result<()> {
         account_password: None,
     };
 
-    let service = manager
+    let service = create_service_with_retry(&manager, &service_info, deleted_existing)
-        .create_service(&service_info, ServiceAccess::CHANGE_CONFIG)
         .context("failed to create the GuruConnect managed agent service")?;
 
     service
@@ -300,6 +307,56 @@ pub fn install_service(exe_path: &std::path::Path) -> Result<()> {
     Ok(())
 }
 
+/// Create the service, retrying briefly if the SCM still has the prior instance
+/// "marked for deletion" (SPEC-018 finding L1).
+///
+/// When a service is deleted, the SCM only removes it from its database once every
+/// open handle to it closes; until then a fresh `CreateService` fails with
+/// `ERROR_SERVICE_MARKED_FOR_DELETE` (1072). The previous implementation papered
+/// over this with a fixed 2s sleep after `delete()`, which is both slower than
+/// necessary in the common case and still racy on a busy box. Instead we attempt
+/// the create immediately and, only if we just deleted an existing instance and
+/// hit 1072, retry a few times with short backoff — succeeding as soon as the SCM
+/// finishes the removal, and giving up with the real error if it never does.
+///
+/// The retry is gated on `deleted_existing`: on a clean first install there was no
+/// prior instance, so a 1072 there is unexpected and is surfaced immediately
+/// rather than masked by retries.
+fn create_service_with_retry(
+    manager: &ServiceManager,
+    service_info: &ServiceInfo,
+    deleted_existing: bool,
+) -> Result<windows_service::service::Service, windows_service::Error> {
+    // ERROR_SERVICE_MARKED_FOR_DELETE (winerror.h). The service is gone from the
+    // caller's perspective but the SCM has not finished reaping it.
+    const ERROR_SERVICE_MARKED_FOR_DELETE: i32 = 1072;
+    // Bounded: ~5 attempts over ~2s total worst case (matches the old fixed sleep
+    // ceiling) but returns the instant the SCM is ready.
+    const MAX_ATTEMPTS: u32 = 5;
+    const BACKOFF: Duration = Duration::from_millis(400);
+
+    let mut attempt = 0;
+    loop {
+        attempt += 1;
+        match manager.create_service(service_info, ServiceAccess::CHANGE_CONFIG) {
+            Ok(service) => return Ok(service),
+            Err(windows_service::Error::Winapi(ref io_err))
+                if deleted_existing
+                    && io_err.raw_os_error() == Some(ERROR_SERVICE_MARKED_FOR_DELETE)
+                    && attempt < MAX_ATTEMPTS =>
+            {
+                warn!(
+                    "{SERVICE_NAME} still marked for deletion by the SCM \
+                     (attempt {attempt}/{MAX_ATTEMPTS}); retrying in {}ms",
+                    BACKOFF.as_millis()
+                );
+                std::thread::sleep(BACKOFF);
+            }
+            Err(e) => return Err(e),
+        }
+    }
+}
+
 /// Configure SCM crash-recovery so the service restarts on unexpected exit.
 ///
 /// `windows-service` 0.7 does not expose `ChangeServiceConfig2` recovery actions
@@ -429,6 +486,12 @@ mod tests {
     /// `service-run` subcommand `main.rs` dispatches into [`run_dispatcher`]; a
     /// mismatch would register a service the SCM could start but that would fall
     /// through to normal (non-service) mode and immediately exit.
+    ///
+    /// This pins the value of the constant itself. The companion test
+    /// `tests::service_run_subcommand_matches_scm_launch_arg` in `main.rs` pins the
+    /// other half — that the clap `#[command(name = "service-run")]` attribute on
+    /// `Commands::ServiceRun` resolves to this same constant — so the two string
+    /// literals cannot silently drift apart.
     #[test]
     fn service_run_arg_matches_subcommand_name() {
         assert_eq!(SERVICE_RUN_ARG, "service-run");

agent/src/session/mod.rs

@@ -41,8 +41,18 @@ use crate::proto::{message, AgentStatus, ChatMessage, Heartbeat, HeartbeatAck, M
 use crate::transport::WebSocketTransport;
 use crate::tray::{TrayAction, TrayController};
 use anyhow::Result;
+use std::sync::atomic::{AtomicBool, Ordering};
+use std::sync::Arc;
 use std::time::{Duration, Instant};
 
+/// Sentinel error string returned by [`SessionManager::run_with_tray`] when the
+/// loop breaks because the SCM asked the managed-agent service to stop (SPEC-018,
+/// finding H). The outer `run_agent` loop matches on this to treat the exit as a
+/// graceful service stop (clean WS close, no reconnect) rather than a session
+/// error. Only the service path passes a shutdown flag, so only the service path
+/// can ever produce this.
+pub const SERVICE_STOP_SENTINEL: &str = "SERVICE_STOP";
+
 // Heartbeat interval (30 seconds)
 const HEARTBEAT_INTERVAL: Duration = Duration::from_secs(30);
 // Status report interval (60 seconds)
@@ -285,16 +295,34 @@ impl SessionManager {
         Ok(())
     }
 
-    /// Run the session main loop with tray and chat event processing
+    /// Run the session main loop with tray and chat event processing.
+    ///
+    /// `service_shutdown` (SPEC-018 finding H) is the SCM cooperative-stop flag.
+    /// It is `Some(flag)` ONLY on the managed-agent service path; the
+    /// attended/viewer/interactive callers pass `None` and behave EXACTLY as
+    /// before. When present, the flag is polled on every idle tick (the natural
+    /// ~100ms seam below) so an SCM Stop/Shutdown received while CONNECTED breaks
+    /// this inner loop promptly — instead of only being observed by the outer
+    /// `run_agent` reconnect loop, which never runs while a session is connected.
+    /// On a set flag the loop closes the WebSocket cleanly (via the shared exit
+    /// path at the bottom) and returns the [`SERVICE_STOP_SENTINEL`] error, which
+    /// the outer loop maps to a graceful stop.
     pub async fn run_with_tray(
         &mut self,
         tray: Option<&TrayController>,
         chat: Option<&ChatController>,
+        service_shutdown: Option<&Arc<AtomicBool>>,
     ) -> Result<()> {
         if self.transport.is_none() {
             anyhow::bail!("Not connected");
         }
 
+        // Helper: has the SCM asked the service to stop? Always false off the
+        // service path (where `service_shutdown` is `None`).
+        let stop_requested = |flag: Option<&Arc<AtomicBool>>| -> bool {
+            flag.is_some_and(|f| f.load(Ordering::SeqCst))
+        };
+
         // Send initial status
         self.send_status().await?;
 
@@ -307,6 +335,29 @@ impl SessionManager {
 
         // Main loop
         loop {
+            // SPEC-018 (finding H): honour an SCM stop request received while the
+            // session is CONNECTED. The outer `run_agent` loop only observes the
+            // flag between connection attempts, but a managed agent spends its
+            // entire connected life inside THIS loop — so without this check an
+            // SCM Stop while connected would not break out until the connection
+            // dropped on its own. Breaking here falls through to the shared exit
+            // path below, which closes the transport cleanly (clean WS close);
+            // the sentinel tells the outer loop this was a graceful stop.
+            if stop_requested(service_shutdown) {
+                tracing::info!("Service stop requested; ending connected session loop");
+                self.release_streaming();
+                self.state = SessionState::Disconnected;
+                if let Some(transport) = self.transport.as_mut() {
+                    // Best-effort clean WebSocket close (sends a Close frame). A
+                    // failure here just means the peer/socket is already gone; the
+                    // service still stops cleanly.
+                    if let Err(e) = transport.close().await {
+                        tracing::warn!("error during clean WebSocket close on service stop: {}", e);
+                    }
+                }
+                return Err(anyhow::anyhow!(SERVICE_STOP_SENTINEL));
+            }
+
             // Process tray events
             if let Some(t) = tray {
                 if let Some(action) = t.process_events() {
@@ -745,3 +796,47 @@ impl SessionManager {
         Ok(())
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    /// SPEC-018 finding H: the connected-stop contract. When the SCM sets the
+    /// shutdown flag, `run_with_tray` returns an error whose message contains
+    /// [`SERVICE_STOP_SENTINEL`]; the outer `run_agent` loop recognises a graceful
+    /// stop with `error_msg.contains(SERVICE_STOP_SENTINEL)`. This pins that the
+    /// error the loop constructs on stop actually satisfies that match — so the
+    /// two halves (producer here, consumer in `main.rs`) cannot drift.
+    ///
+    /// A full end-to-end test of the in-loop interrupt would need a live connected
+    /// transport (a real or mocked server), which is an integration concern; this
+    /// unit test instead pins the wire contract the interrupt relies on.
+    #[test]
+    fn service_stop_sentinel_is_matched_by_outer_loop_check() {
+        let produced = anyhow::anyhow!(SERVICE_STOP_SENTINEL);
+        assert!(
+            produced.to_string().contains(SERVICE_STOP_SENTINEL),
+            "the stop error must contain the sentinel the outer loop matches on"
+        );
+        assert!(
+            !SERVICE_STOP_SENTINEL.is_empty(),
+            "the sentinel must be a non-empty, distinctive token"
+        );
+    }
+
+    /// The shutdown-flag check is a no-op (always `false`) when no flag is passed,
+    /// i.e. on the attended/viewer/interactive paths — guaranteeing the new
+    /// parameter is a pure addition that cannot alter non-service behaviour
+    /// (SPEC-018 finding H: "no regression").
+    #[test]
+    fn no_shutdown_flag_never_requests_stop() {
+        let none: Option<&Arc<AtomicBool>> = None;
+        let check = |flag: Option<&Arc<AtomicBool>>| flag.is_some_and(|f| f.load(Ordering::SeqCst));
+        assert!(!check(none));
+
+        let set = Arc::new(AtomicBool::new(true));
+        assert!(check(Some(&set)));
+        let unset = Arc::new(AtomicBool::new(false));
+        assert!(!check(Some(&unset)));
+    }
+}