diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2da58d7629..045a86ee67 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -56,6 +56,8 @@ Canonical reference for changes, improvements, and bugfixes for Boundary.
 * cli: Fix issue when using the `authenticate` command against a password auth
   method on Windows where the password would be swallowed when the login name is
   submitted ([PR](https://github.com/hashicorp/boundary/pull/3800))
+* worker: Fix an issue that could cause intermittent startup issues on slow
+  systems ([PR](https://github.com/hashicorp/boundary/pull/3803))
 
 ## 0.13.1 (2023/07/10)
 
diff --git a/internal/daemon/worker/controller_connection.go b/internal/daemon/worker/controller_connection.go
index a96402efd1..2dc2a2f636 100644
--- a/internal/daemon/worker/controller_connection.go
+++ b/internal/daemon/worker/controller_connection.go
@@ -162,12 +162,12 @@ func (w *Worker) upstreamDialerFunc(extraAlpnProtos ...string) func(context.Cont
 			default:
 				// In this case, event, so that the operator can understand that
 				// it was rejected
-				event.WriteError(ctx, op, fmt.Errorf("controller rejected activation token as invalid"))
+				event.WriteError(w.baseContext, op, fmt.Errorf("controller rejected activation token as invalid"))
 				return nil, errors.Wrap(w.baseContext, err, op)
 			}
 
 		default:
-			event.WriteError(ctx, op, err)
+			event.WriteError(w.baseContext, op, err)
 			return nil, errors.Wrap(w.baseContext, err, op)
 		}
 
@@ -176,7 +176,7 @@ func (w *Worker) upstreamDialerFunc(extraAlpnProtos ...string) func(context.Cont
 				w.everAuthenticated.Store(authenticationStatusFirstAuthentication)
 			}
 
-			event.WriteSysEvent(ctx, op, "worker has successfully authenticated")
+			event.WriteSysEvent(w.baseContext, op, "worker has successfully authenticated")
 		}
 
 		return conn, err
@@ -204,13 +204,13 @@ func (w *Worker) v1KmsAuthDialFn(ctx context.Context, addr string, extraAlpnProt
 	written, err := tlsConn.Write([]byte(authInfo.ConnectionNonce))
 	if err != nil {
 		if err := nonTlsConn.Close(); err != nil {
-			event.WriteError(ctx, op, err, event.WithInfoMsg("error closing connection after writing failure"))
+			event.WriteError(w.baseContext, op, err, event.WithInfoMsg("error closing connection after writing failure"))
 		}
 		return nil, fmt.Errorf("unable to write connection nonce: %w", err)
 	}
 	if written != len(authInfo.ConnectionNonce) {
 		if err := nonTlsConn.Close(); err != nil {
-			event.WriteError(ctx, op, err, event.WithInfoMsg("error closing connection after writing failure"))
+			event.WriteError(w.baseContext, op, err, event.WithInfoMsg("error closing connection after writing failure"))
 		}
 		return nil, fmt.Errorf("expected to write %d bytes of connection nonce, wrote %d", len(authInfo.ConnectionNonce), written)
 	}