diff --git a/internal/daemon/worker/handler.go b/internal/daemon/worker/handler.go
index 5b2178b9bf..52b57fa914 100644
--- a/internal/daemon/worker/handler.go
+++ b/internal/daemon/worker/handler.go
@@ -194,6 +194,7 @@ func (w *Worker) handleProxy(listenerCfg *listenerutil.ListenerConfig) (http.Han
 					}
 					return
 				}
+				event.WriteSysEvent(ctx, op, "session successfully activated", "session_id", sessionId)
 			}
 		}
 
@@ -234,7 +235,12 @@ func (w *Worker) handleProxy(listenerCfg *listenerutil.ListenerConfig) (http.Han
 			}
 			return
 		}
-		defer session.CloseConnections(ctx, sessClient, w.sessionInfoMap, map[string]string{ci.Id: si.Id})
+		event.WriteSysEvent(ctx, op, "connection successfully authorized", "session_id", sessionId, "connection_id", ci.Id)
+		defer func() {
+			if session.CloseConnections(ctx, sessClient, w.sessionInfoMap, map[string]string{ci.Id: si.Id}) {
+				event.WriteSysEvent(ctx, op, "connection closed", "session_id", sessionId, "connection_id", ci.Id)
+			}
+		}()
 
 		si.Lock()
 		ci.ConnCtx = connCtx
diff --git a/internal/daemon/worker/session/session.go b/internal/daemon/worker/session/session.go
index 346c9a7954..f2eed4f2a4 100644
--- a/internal/daemon/worker/session/session.go
+++ b/internal/daemon/worker/session/session.go
@@ -112,19 +112,20 @@ func closeConnection(ctx context.Context, sessClient pbs.SessionServiceClient, r
 	return resp, nil
 }
 
-// CloseConnections is a helper worker function that sends connection
-// close requests to the controller, and sets close times within the
-// worker. It is called during the worker status loop and on
-// connection exit on the proxy.
+// CloseConnections is a helper worker function that sends connection close
+// requests to the controller, and sets close times within the worker. It is
+// called during the worker status loop and on connection exit on the proxy.
 //
-// closeInfo is a map of connections mapped to their individual
-// session.
-func CloseConnections(ctx context.Context, sessClient pbs.SessionServiceClient, sessionInfo *sync.Map, closeInfo map[string]string) {
+// The boolean indicates whether the function was successful, e.g. had any
+// errors. Individual events will be sent for the errors if there are any.
+//
+// closeInfo is a map of connections mapped to their individual session.
+func CloseConnections(ctx context.Context, sessClient pbs.SessionServiceClient, sessionInfo *sync.Map, closeInfo map[string]string) bool {
 	const op = "session.CloseConnections"
 	if closeInfo == nil {
 		// This should not happen, but it's a no-op if it does. Just
 		// return.
-		return
+		return false
 	}
 
 	// How we handle close info depends on whether or not we succeeded with
@@ -155,7 +156,7 @@ func CloseConnections(ctx context.Context, sessClient pbs.SessionServiceClient,
 
 	if err != nil {
 		event.WriteError(ctx, op, err, event.WithInfoMsg("serious error in processing return data from controller, aborting additional session/connection state modification"))
-		return
+		return false
 	}
 
 	// Mark connections as closed
@@ -164,7 +165,10 @@ func CloseConnections(ctx context.Context, sessClient pbs.SessionServiceClient,
 		for _, err := range errs {
 			event.WriteError(ctx, op, err, event.WithInfoMsg("error marking connection closed in state"))
 		}
+		return false
 	}
+
+	return true
 }
 
 // makeCloseConnectionRequest creates a CloseConnectionRequest for
diff --git a/internal/daemon/worker/status.go b/internal/daemon/worker/status.go
index 9d312a6d7a..91d789214f 100644
--- a/internal/daemon/worker/status.go
+++ b/internal/daemon/worker/status.go
@@ -322,7 +322,7 @@ func (w *Worker) cleanupConnections(cancelCtx context.Context, ignoreSessionStat
 		if err != nil {
 			event.WriteError(cancelCtx, op, err, event.WithInfo("failed to create controller session client, connections won't be cleaned up"))
 		} else {
-			session.CloseConnections(cancelCtx, sessClient, w.sessionInfoMap, closeInfo)
+			_ = session.CloseConnections(cancelCtx, sessClient, w.sessionInfoMap, closeInfo)
 		}
 	}