diff --git a/charts/stable/cloudflared/Chart.yaml b/charts/stable/cloudflared/Chart.yaml
index 2135326561d..4d4056785d8 100644
--- a/charts/stable/cloudflared/Chart.yaml
+++ b/charts/stable/cloudflared/Chart.yaml
@@ -9,7 +9,7 @@ annotations:
   trueforge.org/min_helm_version: "3.14"
   trueforge.org/train: stable
 apiVersion: v2
-appVersion: 2026.5.1
+appVersion: 2026.5.2
 dependencies:
   - name: common
     version: 29.3.4
@@ -35,5 +35,5 @@ sources:
   - https://github.com/trueforge-org/truecharts/tree/master/charts/stable/cloudflared
   - https://hub.docker.com/r/cloudflare/cloudflared
 type: application
-version: 16.4.1
+version: 16.4.2
 
diff --git a/charts/stable/cloudflared/values.yaml b/charts/stable/cloudflared/values.yaml
index 59322f4badc..dc855180bc4 100644
--- a/charts/stable/cloudflared/values.yaml
+++ b/charts/stable/cloudflared/values.yaml
@@ -2,7 +2,7 @@
 image:
   repository: docker.io/cloudflare/cloudflared
   pullPolicy: IfNotPresent
-  tag: 2026.5.1@sha256:a5b5e6fd9a372f054b9a843c219bfbcdceb54691605312a8b1ee72978bdf1aa1
+  tag: 2026.5.2@sha256:12ff5c6992a9863db4da270746af7c244bcaee49353039af8104268a18d6c4f0
 workload:
   main:
     podSpec: