diff --git a/pkg/kv/kvclient/kvtenant/setting_overrides.go b/pkg/kv/kvclient/kvtenant/setting_overrides.go
index 278d88cf3f19..bb8a9fb5d1ee 100644
--- a/pkg/kv/kvclient/kvtenant/setting_overrides.go
+++ b/pkg/kv/kvclient/kvtenant/setting_overrides.go
@@ -38,6 +38,16 @@ func (c *connector) runTenantSettingsSubscription(ctx context.Context, startupCh
 			c.tryForgetClient(ctx, client)
 			continue
 		}
+
+		// Reset the sentinel checks. We start a new sequence of messages
+		// from the server every time we (re)connect.
+		func() {
+			c.settingsMu.Lock()
+			defer c.settingsMu.Unlock()
+			c.settingsMu.receivedFirstAllTenantOverrides = false
+			c.settingsMu.receivedFirstSpecificOverrides = false
+		}()
+
 		for {
 			e, err := stream.Recv()
 			if err != nil {
@@ -51,7 +61,8 @@ func (c *connector) runTenantSettingsSubscription(ctx context.Context, startupCh
 			}
 			if e.Error != (errorspb.EncodedError{}) {
 				// Hard logical error. We expect io.EOF next.
-				log.Errorf(ctx, "error consuming TenantSettings RPC: %v", e.Error)
+				err := errors.DecodeError(ctx, e.Error)
+				log.Errorf(ctx, "error consuming TenantSettings RPC: %v", err)
 				continue
 			}
 
@@ -83,18 +94,29 @@ func (c *connector) processSettingsEvent(
 	c.settingsMu.Lock()
 	defer c.settingsMu.Unlock()
 
-	if (!c.settingsMu.receivedFirstAllTenantOverrides || !c.settingsMu.receivedFirstSpecificOverrides) && e.Incremental {
-		return false, errors.Newf("need to receive non-incremental setting events first")
-	}
-
 	var m map[string]settings.EncodedValue
 	switch e.Precedence {
 	case kvpb.TenantSettingsEvent_ALL_TENANTS_OVERRIDES:
+		if !c.settingsMu.receivedFirstAllTenantOverrides && e.Incremental {
+			return false, errors.Newf(
+				"need to receive non-incremental setting event first for precedence %v",
+				e.Precedence,
+			)
+		}
+
 		c.settingsMu.receivedFirstAllTenantOverrides = true
 		m = c.settingsMu.allTenantOverrides
+
 	case kvpb.TenantSettingsEvent_TENANT_SPECIFIC_OVERRIDES:
+		if !c.settingsMu.receivedFirstSpecificOverrides && e.Incremental {
+			return false, errors.Newf(
+				"need to receive non-incremental setting events first for precedence %v",
+				e.Precedence,
+			)
+		}
 		c.settingsMu.receivedFirstSpecificOverrides = true
 		m = c.settingsMu.specificOverrides
+
 	default:
 		return false, errors.Newf("unknown precedence value %d", e.Precedence)
 	}
diff --git a/pkg/server/settingswatcher/settings_watcher.go b/pkg/server/settingswatcher/settings_watcher.go
index 0154c5bd864b..2a2997006632 100644
--- a/pkg/server/settingswatcher/settings_watcher.go
+++ b/pkg/server/settingswatcher/settings_watcher.go
@@ -366,8 +366,9 @@ func (s *SettingsWatcher) updateOverrides(ctx context.Context) {
 		if key == versionSettingKey {
 			var newVersion clusterversion.ClusterVersion
 			if err := protoutil.Unmarshal([]byte(val.Value), &newVersion); err != nil {
-				log.Warningf(ctx, "ignoring invalid cluster version: %newVersion - "+
-					"the lack of a refreshed storage cluster version in a secondary tenant may prevent tenant upgrade", err)
+				log.Warningf(ctx, "ignoring invalid cluster version: %s - %v\n"+
+					"Note: the lack of a refreshed storage cluster version in a secondary tenant may prevent tenant upgrade.",
+					newVersion, err)
 			} else {
 				// We don't want to fully process the override in the case
 				// where we're dealing with the "version" setting, as we want