diff --git a/bucket/cloudflared.json b/bucket/cloudflared.json
index 54741b9a21..cd977ba5db 100644
--- a/bucket/cloudflared.json
+++ b/bucket/cloudflared.json
@@ -1,5 +1,5 @@
 {
-    "version": "2021.5.5",
+    "version": "2021.5.6",
     "description": "Command-line client to interact with Cloudflare's Argo Tunnel, Cloudflare Access, start up a DNS over HTTPS resolver and more.",
     "homepage": "https://github.com/cloudflare/cloudflared",
     "license": {
@@ -8,12 +8,12 @@
     },
     "architecture": {
         "64bit": {
-            "url": "https://github.com/cloudflare/cloudflared/releases/download/2021.5.5/cloudflared-windows-amd64.exe#/cloudflared.exe",
-            "hash": "b1b488c7cd1c9cc25c177960fef12dd81888ca2a4de6dbd50dc1c22f0758336d"
+            "url": "https://github.com/cloudflare/cloudflared/releases/download/2021.5.6/cloudflared-windows-amd64.exe#/cloudflared.exe",
+            "hash": "3e766e30ad76d503668f06fa1b56d98da5268e0e72bff6cc3f5eaf9aa3cdf580"
         },
         "32bit": {
-            "url": "https://github.com/cloudflare/cloudflared/releases/download/2021.5.5/cloudflared-windows-386.exe#/cloudflared.exe",
-            "hash": "b3a558787c97fd92cd18d6726122156796e4a1eae3865bb9eeb41b27eb92a05e"
+            "url": "https://github.com/cloudflare/cloudflared/releases/download/2021.5.6/cloudflared-windows-386.exe#/cloudflared.exe",
+            "hash": "f7dc4afb512fdbb42dab35af5fd899479dbb15f6f664c74eada5d29f9fd33005"
         }
     },
     "bin": "cloudflared.exe",