diff --git a/go/vt/topotools/routing_rules.go b/go/vt/topotools/routing_rules.go
index a3bc5a8a957..9056eef4283 100644
--- a/go/vt/topotools/routing_rules.go
+++ b/go/vt/topotools/routing_rules.go
@@ -189,6 +189,7 @@ func UpdateKeyspaceRoutingRules(ctx context.Context, ts *topo.Server, reason str
 	if lockErr != nil {
 		// If the key does not yet exist then let's create it.
 		if !topo.IsErrType(lockErr, topo.NoNode) {
+			log.Warningf("Failed to lock keyspace routing rules: %v", lockErr)
 			return lockErr
 		}
 		rules := make(map[string]string)
@@ -198,7 +199,9 @@ func UpdateKeyspaceRoutingRules(ctx context.Context, ts *topo.Server, reason str
 		// This will fail if the key already exists and thus avoids any races here. The first
 		// writer will win and the others will have to retry. This situation should be very
 		// rare as we are typically only updating the rules from here on out.
+		log.Warningf("Creating keyspace routing rules for the first time")
 		if err := ts.CreateKeyspaceRoutingRules(ctx, buildKeyspaceRoutingRules(&rules)); err != nil {
+			log.Warningf("Failed to create keyspace routing rules: %v", err)
 			return err
 		}
 		return nil
@@ -209,6 +212,7 @@ func UpdateKeyspaceRoutingRules(ctx context.Context, ts *topo.Server, reason str
 		return err
 	}
 	if err := update(lockCtx, &rules); err != nil {
+		log.Warningf("Failed to update keyspace routing rules: %v", err)
 		return err
 	}
 	if err := saveKeyspaceRoutingRulesLocked(lockCtx, ts, rules); err != nil {
diff --git a/go/vt/vtctl/workflow/utils.go b/go/vt/vtctl/workflow/utils.go
index d4e8d7b4ec0..02cdd0403b8 100644
--- a/go/vt/vtctl/workflow/utils.go
+++ b/go/vt/vtctl/workflow/utils.go
@@ -882,7 +882,10 @@ func updateKeyspaceRoutingRules(ctx context.Context, ts *topo.Server, reason str
 	// If we were racing with another caller to create the initial routing rules, then
 	// we can immediately retry the operation.
 	if !topo.IsErrType(err, topo.NodeExists) {
+		log.Warningf("failed to update keyspace routing rules, NOT topo.NodeExists: %v", err)
 		return err
+	} else {
+		log.Warningf("failed to update keyspace routing rules, GOT topo.NodeExists, retrying: %v", err)
 	}
 	return update()
 }