diff --git a/windows-agent/internal/proservices/proservices.go b/windows-agent/internal/proservices/proservices.go
index 681bfc104..ceccbda4d 100644
--- a/windows-agent/internal/proservices/proservices.go
+++ b/windows-agent/internal/proservices/proservices.go
@@ -9,6 +9,7 @@ import (
 
 	agent_api "github.com/canonical/ubuntu-pro-for-windows/agentapi/go"
 	"github.com/canonical/ubuntu-pro-for-windows/common"
+	"github.com/canonical/ubuntu-pro-for-windows/windows-agent/internal/cloudinit"
 	"github.com/canonical/ubuntu-pro-for-windows/windows-agent/internal/config"
 	"github.com/canonical/ubuntu-pro-for-windows/windows-agent/internal/distros/database"
 	"github.com/canonical/ubuntu-pro-for-windows/windows-agent/internal/grpc/interceptorschain"
@@ -99,6 +100,16 @@ func New(ctx context.Context, args ...Option) (s Manager, err error) {
 
 	conf := config.New(ctx, opts.cacheDir)
 
+	// Write cloud-init agent data, and do so again every time the config changes.
+	f := func() {
+		if err := cloudinit.WriteAgentData(ctx, conf); err != nil {
+			log.Error(ctx, err)
+		}
+	}
+
+	f()
+	conf.Notify(f)
+
 	db, err := database.New(ctx, opts.cacheDir, conf)
 	if err != nil {
 		return s, err