diff --git a/bucket/cloudflared.json b/bucket/cloudflared.json
index c7b4e3588e..54741b9a21 100644
--- a/bucket/cloudflared.json
+++ b/bucket/cloudflared.json
@@ -1,5 +1,5 @@
 {
-    "version": "2021.5.4",
+    "version": "2021.5.5",
     "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/2021.5.4/cloudflared-windows-amd64.exe#/cloudflared.exe",
-            "hash": "e0b3c15c3cad2af9c6704c3a2b68f11dbe6d47536e7ec1f3974f77fd50e483c0"
+            "url": "https://github.com/cloudflare/cloudflared/releases/download/2021.5.5/cloudflared-windows-amd64.exe#/cloudflared.exe",
+            "hash": "b1b488c7cd1c9cc25c177960fef12dd81888ca2a4de6dbd50dc1c22f0758336d"
         },
         "32bit": {
-            "url": "https://github.com/cloudflare/cloudflared/releases/download/2021.5.4/cloudflared-windows-386.exe#/cloudflared.exe",
-            "hash": "080d7f69258cd6b25326c319aa79254162f97a34143df4c4a3b87f7ccceb2947"
+            "url": "https://github.com/cloudflare/cloudflared/releases/download/2021.5.5/cloudflared-windows-386.exe#/cloudflared.exe",
+            "hash": "b3a558787c97fd92cd18d6726122156796e4a1eae3865bb9eeb41b27eb92a05e"
         }
     },
     "bin": "cloudflared.exe",