diff --git a/flake.nix b/flake.nix
index 633c389b8f516..57fc346a74c63 100644
--- a/flake.nix
+++ b/flake.nix
@@ -117,7 +117,7 @@
             name = "coder-${osArch}";
             # Updated with ./scripts/update-flake.sh`.
             # This should be updated whenever go.mod changes!
-            vendorHash = "sha256-tqVppjRTsyZOQ7ZOg7HCiFgfJWAHFjb2GsZEJvxL5i8=";
+            vendorHash = "sha256-RtAdfYeBXm+X/BKc+ExOOhQx1NcGNxOXK3ZMmHi2dlg=";
             proxyVendor = true;
             src = ./.;
             nativeBuildInputs = with pkgs; [ getopt openssl zstd ];
diff --git a/go.mod b/go.mod
index 717b94845dbff..000ad1c89f63a 100644
--- a/go.mod
+++ b/go.mod
@@ -187,7 +187,7 @@ require (
 	golang.org/x/tools v0.24.0
 	golang.org/x/xerrors v0.0.0-20240716161551-93cc26a95ae9
 	google.golang.org/api v0.195.0
-	google.golang.org/grpc v1.65.0
+	google.golang.org/grpc v1.66.0
 	google.golang.org/protobuf v1.34.2
 	gopkg.in/DataDog/dd-trace-go.v1 v1.67.0
 	gopkg.in/natefinch/lumberjack.v2 v2.2.1
diff --git a/go.sum b/go.sum
index 922063b85cc1c..7d619804d778e 100644
--- a/go.sum
+++ b/go.sum
@@ -1226,8 +1226,8 @@ google.golang.org/grpc v1.23.0/go.mod h1:Y5yQAOtifL1yxbo5wqy6BxZv8vAUGQwXBOALyac
 google.golang.org/grpc v1.25.1/go.mod h1:c3i+UQWmh7LiEpx4sFZnkU36qjEYZ0imhYfXVyQciAY=
 google.golang.org/grpc v1.27.0/go.mod h1:qbnxyOmOxrQa7FizSgH+ReBfzJrCY1pSN7KXBS8abTk=
 google.golang.org/grpc v1.33.2/go.mod h1:JMHMWHQWaTccqQQlmk3MJZS+GWXOdAesneDmEnv2fbc=
-google.golang.org/grpc v1.65.0 h1:bs/cUb4lp1G5iImFFd3u5ixQzweKizoZJAwBNLR42lc=
-google.golang.org/grpc v1.65.0/go.mod h1:WgYC2ypjlB0EiQi6wdKixMqukr6lBc0Vo+oOgjrM5ZQ=
+google.golang.org/grpc v1.66.0 h1:DibZuoBznOxbDQxRINckZcUvnCEvrW9pcWIE2yF9r1c=
+google.golang.org/grpc v1.66.0/go.mod h1:s3/l6xSSCURdVfAnL+TqCNMyTDAGN6+lZeVxnZR128Y=
 google.golang.org/protobuf v0.0.0-20200109180630-ec00e32a8dfd/go.mod h1:DFci5gLYBciE7Vtevhsrf46CRTquxDuWsQurQQe4oz8=
 google.golang.org/protobuf v0.0.0-20200221191635-4d8936d0db64/go.mod h1:kwYJMbMJ01Woi6D6+Kah6886xMZcty6N08ah7+eCXa0=
 google.golang.org/protobuf v0.0.0-20200228230310-ab0ca4ff8a60/go.mod h1:cfTl7dwQJ+fmap5saPgwCLgHXTUD7jkjRqWcaiX5VyM=