diff --git a/charts/cloudflared/Chart.yaml b/charts/cloudflared/Chart.yaml
index 543ca01..67ca4dd 100644
--- a/charts/cloudflared/Chart.yaml
+++ b/charts/cloudflared/Chart.yaml
@@ -1,6 +1,6 @@
 apiVersion: v2
 name: cloudflared
-version: 1.14.3
+version: 1.14.4
 description: Cloudflared Tunnel
 keywords:
   - cloudflare
@@ -15,4 +15,4 @@ dependencies:
     repository: https://bjw-s.github.io/helm-charts/
     version: 3.7.3
 icon: https://avatars.githubusercontent.com/u/314135?s=48&v=4
-appVersion: "2025.2.1"
+appVersion: "2025.5.0"
diff --git a/charts/cloudflared/README.md b/charts/cloudflared/README.md
index 5487769..2e1bf4f 100644
--- a/charts/cloudflared/README.md
+++ b/charts/cloudflared/README.md
@@ -1,6 +1,6 @@
 # cloudflared
 
-![Version: 1.14.3](https://img.shields.io/badge/Version-1.14.3-informational?style=flat-square) ![AppVersion: 2025.2.1](https://img.shields.io/badge/AppVersion-2025.2.1-informational?style=flat-square)
+![Version: 1.14.4](https://img.shields.io/badge/Version-1.14.4-informational?style=flat-square) ![AppVersion: 2025.5.0](https://img.shields.io/badge/AppVersion-2025.5.0-informational?style=flat-square)
 
 Cloudflared Tunnel
 
@@ -27,7 +27,7 @@ Cloudflared Tunnel
 |-----|------|---------|-------------|
 | existingSecretKey | string | `"cf-tunnel-token"` | Name of key that contains the token in the existingSecret |
 | existingSecretName | string | `"cloudflared-secret"` | Name of existing secret that contains Cloudflare token |
-| image | object | `{"pullPolicy":"IfNotPresent","repository":"cloudflare/cloudflared","tag":"2025.2.1"}` | Default image |
+| image | object | `{"pullPolicy":"IfNotPresent","repository":"cloudflare/cloudflared","tag":"2025.5.0"}` | Default image |
 | name | string | `"cloudflared"` | Name override of release |
 | resources | object | `{"requests":{"cpu":"10m","memory":"128Mi"}}` | Default resources |
 
diff --git a/charts/cloudflared/values.yaml b/charts/cloudflared/values.yaml
index 4ae251c..6881351 100644
--- a/charts/cloudflared/values.yaml
+++ b/charts/cloudflared/values.yaml
@@ -10,7 +10,7 @@ existingSecretKey: cf-tunnel-token
 # -- Default image
 image:
   repository: cloudflare/cloudflared
-  tag: "2025.2.1"
+  tag: "2025.5.0"
   pullPolicy: IfNotPresent
 
 # -- Default resources