diff --git a/bucket/doctl.json b/bucket/doctl.json
index c7ee4c9bc2..c869fd13e5 100644
--- a/bucket/doctl.json
+++ b/bucket/doctl.json
@@ -1,16 +1,16 @@
 {
     "description": "A command line tool for Digital Ocean services",
     "homepage": "https://github.com/digitalocean/doctl",
-    "version": "1.20.1",
+    "version": "1.21.1",
     "license": "Apache-2.0",
     "architecture": {
         "64bit": {
-            "url": "https://github.com/digitalocean/doctl/releases/download/v1.20.1/doctl-1.20.1-windows-4.0-amd64.zip",
-            "hash": "23e92b714f5c76f18b5ad32a88f3618a392a9d7c36b9eb900c7e361188bea18d"
+            "url": "https://github.com/digitalocean/doctl/releases/download/v1.21.1/doctl-1.21.1-windows-amd64.zip",
+            "hash": "75677aaf23980dd740d74f9a9b7cbf1fb043a1d53787b0460955e8b92c37faef"
         },
         "32bit": {
-            "url": "https://github.com/digitalocean/doctl/releases/download/v1.20.1/doctl-1.20.1-windows-4.0-386.zip",
-            "hash": "f4b479bfc2be4beab2b307dae592d1271403745e64bd0687a617befb13baa068"
+            "url": "https://github.com/digitalocean/doctl/releases/download/v1.21.1/doctl-1.21.1-windows-386.zip",
+            "hash": "7265703d9fa249ae0e478437d00b3f2fd8deb498afb29425ba323e194a6dbab6"
         }
     },
     "bin": "doctl.exe",
@@ -18,14 +18,19 @@
     "autoupdate": {
         "architecture": {
             "64bit": {
-                "url": "https://github.com/digitalocean/doctl/releases/download/v$version/doctl-$version-windows-4.0-amd64.zip"
+                "url": "https://github.com/digitalocean/doctl/releases/download/v$version/doctl-$version-windows-amd64.zip",
+                "hash": {
+                    "url": "$baseurl/doctl-$version-windows-amd64.sha256",
+                    "regex": "$sha256"
+                }
             },
             "32bit": {
-                "url": "https://github.com/digitalocean/doctl/releases/download/v$version/doctl-$version-windows-4.0-386.zip"
+                "url": "https://github.com/digitalocean/doctl/releases/download/v$version/doctl-$version-windows-386.zip",
+                "hash": {
+                    "url": "$baseurl/doctl-$version-windows-386.sha256",
+                    "regex": "$sha256"
+                }
             }
-        },
-        "hash": {
-            "url": "$url.sha256"
         }
     }
 }