diff --git a/bucket/upbound-cli.json b/bucket/upbound-cli.json
index aa3c15172d..f8d3cc5190 100644
--- a/bucket/upbound-cli.json
+++ b/bucket/upbound-cli.json
@@ -1,12 +1,12 @@
 {
-    "version": "0.26.0",
+    "version": "0.27.0",
     "description": "Official CLI for interacting with Upbound Cloud, Upbound Enterprise, and Universal Crossplane (UXP).",
     "homepage": "https://cloud.upbound.io/docs/cli",
     "license": "Apache-2.0",
     "architecture": {
         "64bit": {
-            "url": "https://cli.upbound.io/stable/v0.26.0/bin/windows_amd64/up.exe",
-            "hash": "f1c94014e8eb9b86d9377e44522031288d39b4247806c8fa2b96421b41e108d2"
+            "url": "https://cli.upbound.io/stable/v0.27.0/bin/windows_amd64/up.exe",
+            "hash": "68b769de2a027b4e02c44758d1d459de372f6e2ec98ea515ef7ca1e5ec261526"
         }
     },
     "bin": "up.exe",