fix: surface failed Ticket notification delivery

crates/workspace-server/src/server.rs

@@ -5312,6 +5312,66 @@ fn ticket_notification_content(ticket_id: &str, current_state: &str) -> String {
     )
 }
 
+#[derive(Debug, Clone, Serialize, PartialEq, Eq)]
+struct TicketNotificationDeliveryWarning {
+    level: &'static str,
+    event: &'static str,
+    ticket_id: String,
+    recipient_runtime_id: String,
+    recipient_worker_id: String,
+    error_category: &'static str,
+}
+
+impl TicketNotificationDeliveryWarning {
+    fn new(ticket_id: &str, recipient: &RuntimeWorkerRef, error_category: &'static str) -> Self {
+        Self {
+            level: "warning",
+            event: "ticket_notification_delivery_failed",
+            ticket_id: ticket_id.to_string(),
+            recipient_runtime_id: recipient.runtime_id.clone(),
+            recipient_worker_id: recipient.worker_id.clone(),
+            error_category,
+        }
+    }
+}
+
+#[cfg(test)]
+static TICKET_NOTIFICATION_DELIVERY_WARNING_CAPTURE: Mutex<Vec<TicketNotificationDeliveryWarning>> =
+    Mutex::new(Vec::new());
+
+fn ticket_notification_delivery_error_category(
+    result: &std::result::Result<WorkerInputResult, RuntimeRegistryError>,
+) -> Option<&'static str> {
+    match result {
+        Ok(result) => match result.state {
+            WorkerOperationState::Accepted => None,
+            WorkerOperationState::Rejected => Some("runtime_rejected"),
+            WorkerOperationState::Unsupported => Some("runtime_unsupported"),
+        },
+        Err(RuntimeRegistryError::InvalidIdentifier { .. }) => Some("invalid_identifier"),
+        Err(RuntimeRegistryError::UnknownRuntime(_)) => Some("unknown_runtime"),
+        Err(RuntimeRegistryError::UnknownHost(_)) => Some("unknown_host"),
+        Err(RuntimeRegistryError::UnknownWorker { .. }) => Some("unknown_worker"),
+        Err(RuntimeRegistryError::RuntimeOperationFailed { .. }) => {
+            Some("runtime_operation_failed")
+        }
+    }
+}
+
+fn emit_ticket_notification_delivery_warning(warning: TicketNotificationDeliveryWarning) {
+    let serialized = serde_json::to_string(&warning)
+        .expect("Ticket notification delivery warnings serialize from bounded string fields");
+    eprintln!(
+        "{} yoi-server {serialized}",
+        Utc::now().to_rfc3339_opts(SecondsFormat::Millis, true)
+    );
+    #[cfg(test)]
+    TICKET_NOTIFICATION_DELIVERY_WARNING_CAPTURE
+        .lock()
+        .unwrap_or_else(|poisoned| poisoned.into_inner())
+        .push(warning);
+}
+
 fn notify_ticket_recipients(
     api: &WorkspaceApi,
     workspace_id: &str,
@@ -5343,7 +5403,7 @@ fn notify_ticket_recipients(
         if source.as_ref().is_some_and(|source| source == &recipient) {
             continue;
         }
-        let _ = api.runtime.send_input(
+        let result = api.runtime.send_input(
             &recipient,
             WorkerInputRequest {
                 kind: WorkerInputKind::Notify,
@@ -5351,6 +5411,13 @@ fn notify_ticket_recipients(
                 segments: None,
             },
         );
+        if let Some(error_category) = ticket_notification_delivery_error_category(&result) {
+            emit_ticket_notification_delivery_warning(TicketNotificationDeliveryWarning::new(
+                ticket_id,
+                &recipient,
+                error_category,
+            ));
+        }
     }
 }
 
@@ -15727,7 +15794,7 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn queued_ticket_mutation_succeeds_without_orchestrator() {
+    async fn queued_ticket_mutation_stays_committed_when_notification_recipient_is_missing() {
         let dir = tempfile::tempdir().unwrap();
         let api = test_api(dir.path()).await;
         let source = api
@@ -15766,6 +15833,43 @@ mod tests {
         let mut input = ticket::NewTicket::new("Queued notification");
         input.workflow_state = Some(TicketWorkflowState::Queued);
         let ticket_ref = backend.create(input).unwrap();
+        let missing_recipient =
+            RuntimeWorkerRef::new(EMBEDDED_WORKER_RUNTIME_ID, "missing-notification-recipient");
+        api.store
+            .upsert_worker_registry(&WorkerRegistryRecord {
+                workspace_id: TEST_WORKSPACE_ID.to_string(),
+                worker: missing_recipient.clone(),
+                display_name: "Missing notification recipient".to_string(),
+                profile: Some("builtin:coder".to_string()),
+                retention_state: "normal".to_string(),
+                transcript_ref: None,
+                session_ref: None,
+                summary_ref: None,
+                diagnostics_ref: None,
+                created_at: TEST_CREATED_AT.to_string(),
+                updated_at: TEST_CREATED_AT.to_string(),
+            })
+            .unwrap();
+        api.store
+            .set_current_ticket_worker_assignment(
+                &TicketWorkerAssignmentRecord {
+                    workspace_id: TEST_WORKSPACE_ID.to_string(),
+                    ticket_id: ticket_ref.id.clone(),
+                    assignment_id: "missing-recipient-assignment".to_string(),
+                    worker: missing_recipient.clone(),
+                    assigned_by: "test-user".to_string(),
+                    assigned_at: TEST_CREATED_AT.to_string(),
+                },
+                None,
+                "missing-recipient-assignment-event",
+                "missing-recipient-assignment-operation",
+                false,
+            )
+            .unwrap();
+        TICKET_NOTIFICATION_DELIVERY_WARNING_CAPTURE
+            .lock()
+            .unwrap_or_else(|poisoned| poisoned.into_inner())
+            .retain(|warning| warning.ticket_id != ticket_ref.id);
         let mut headers = HeaderMap::new();
         headers.insert(
             "x-yoi-runtime-id",
@@ -15788,6 +15892,28 @@ mod tests {
         )
         .await
         .unwrap();
+
+        assert_eq!(
+            api.authority.ticket(&ticket_ref.id).unwrap().state,
+            TicketWorkflowState::Queued.as_str()
+        );
+        let warnings = TICKET_NOTIFICATION_DELIVERY_WARNING_CAPTURE
+            .lock()
+            .unwrap_or_else(|poisoned| poisoned.into_inner())
+            .iter()
+            .filter(|warning| warning.ticket_id == ticket_ref.id)
+            .cloned()
+            .collect::<Vec<_>>();
+        assert_eq!(warnings.len(), 1);
+        let warning = &warnings[0];
+        assert_eq!(warning.level, "warning");
+        assert_eq!(warning.event, "ticket_notification_delivery_failed");
+        assert_eq!(warning.recipient_runtime_id, missing_recipient.runtime_id);
+        assert_eq!(warning.recipient_worker_id, missing_recipient.worker_id);
+        assert_eq!(warning.error_category, "unknown_worker");
+        let serialized = serde_json::to_string(warning).unwrap();
+        assert!(!serialized.contains("queued update"));
+        assert!(!serialized.contains("Ticket notification:"));
     }
 
     #[tokio::test]