diff --git a/bucket/upbound-cli.json b/bucket/upbound-cli.json
index 2d46da7648..5f88bd79b2 100644
--- a/bucket/upbound-cli.json
+++ b/bucket/upbound-cli.json
@@ -1,12 +1,12 @@
 {
-    "version": "0.20.0",
+    "version": "0.21.0",
     "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/v0.20.0/bin/windows_amd64/up.exe",
-            "hash": "79766d6af51c7aa467232a5444511fd4361e1f7244124583b75004f03da9a78a"
+            "url": "https://cli.upbound.io/stable/v0.21.0/bin/windows_amd64/up.exe",
+            "hash": "99fc37b3c5ee99d3c509341643a96fe3470e0f0653ced179c15d9aa4dc44d172"
         }
     },
     "bin": "up.exe",