diff --git a/CHANGELOG.md b/CHANGELOG.md
index 365af26..c5e5ebb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,4 +1,5 @@
 # 0.6.2 (Next)
+- Added support for Headscale 0.27.0 and 0.27.1
 - Bundle all `node_modules` aside from native ones to reduce bundle and container size (closes [#331](https://github.com/tale/headplane/issues/331)).
 - Allow conditionally compiling the SSH WASM integration when building (closes [#337](https://github.com/tale/headplane/issues/337)).
 - Implemented the ability to customize the build with a custom script (see `./build.sh --help` for more information).
diff --git a/app/openapi-canonical-families.json b/app/openapi-canonical-families.json
index 5445408..4c95fe2 100644
--- a/app/openapi-canonical-families.json
+++ b/app/openapi-canonical-families.json
@@ -1,4 +1,5 @@
 {
 	"0.26.1": ["0.26.0", "0.26.1"],
-	"0.27.0": ["0.27.0"]
+	"0.27.0": ["0.27.0"],
+	"0.27.1": ["0.27.1"]
 }
diff --git a/app/openapi-operation-hashes.json b/app/openapi-operation-hashes.json
index 37e97e3..d1312dd 100644
--- a/app/openapi-operation-hashes.json
+++ b/app/openapi-operation-hashes.json
@@ -77,5 +77,32 @@
 		"POST /api/v1/user": "a4e1d889d7962da5",
 		"DELETE /api/v1/user/{id}": "3d553e4b74296884",
 		"POST /api/v1/user/{oldId}/rename/{newName}": "996c03ebf81576d7"
+	},
+	"0.27.1": {
+		"GET /api/v1/apikey": "efe31b6dc980e158",
+		"POST /api/v1/apikey": "39953a96c1da5312",
+		"POST /api/v1/apikey/expire": "ca56add866802f17",
+		"DELETE /api/v1/apikey/{prefix}": "3f0125f7abe7abb1",
+		"POST /api/v1/debug/node": "204f9ae3f9f738c6",
+		"GET /api/v1/health": "5e447272e72b2e5f",
+		"GET /api/v1/node": "8bb18b8c7cfb4f20",
+		"POST /api/v1/node/backfillips": "6da4d1d3922a8001",
+		"POST /api/v1/node/register": "539f7cb3a84d43d4",
+		"GET /api/v1/node/{nodeId}": "8a7da3d24dc82c37",
+		"DELETE /api/v1/node/{nodeId}": "f832f33d84fd3724",
+		"POST /api/v1/node/{nodeId}/approve_routes": "e6c22e46ad44903d",
+		"POST /api/v1/node/{nodeId}/expire": "53efc8e2017c16ae",
+		"POST /api/v1/node/{nodeId}/rename/{newName}": "d355388ac934dc90",
+		"POST /api/v1/node/{nodeId}/tags": "b6a8296dcc2939b5",
+		"POST /api/v1/node/{nodeId}/user": "ae3a30b43ffd1922",
+		"GET /api/v1/policy": "d6c639be304cd3c0",
+		"PUT /api/v1/policy": "6cbe80bde771a388",
+		"GET /api/v1/preauthkey": "14db6a04f90d7a7e",
+		"POST /api/v1/preauthkey": "0b4308e049d4eb58",
+		"POST /api/v1/preauthkey/expire": "31f377a66d3a5c4f",
+		"GET /api/v1/user": "228831b58ccc5a17",
+		"POST /api/v1/user": "a4e1d889d7962da5",
+		"DELETE /api/v1/user/{id}": "3d553e4b74296884",
+		"POST /api/v1/user/{oldId}/rename/{newName}": "996c03ebf81576d7"
 	}
 }
diff --git a/tests/generate-openapi-hashes.ts b/tests/generate-openapi-hashes.ts
index fd5d292..9a27084 100644
--- a/tests/generate-openapi-hashes.ts
+++ b/tests/generate-openapi-hashes.ts
@@ -14,6 +14,7 @@ const SPEC_MAP = {
 	'0.26.0': '/v0.26.0/gen/openapiv2/headscale/v1/headscale.swagger.json',
 	'0.26.1': '/v0.26.1/gen/openapiv2/headscale/v1/headscale.swagger.json',
 	'0.27.0': '/v0.27.0/gen/openapiv2/headscale/v1/headscale.swagger.json',
+	'0.27.1': '/v0.27.1/gen/openapiv2/headscale/v1/headscale.swagger.json',
 } as const;
 
 async function hashOpenApiOperations(specUrl: string) {