diff --git a/ee/agent/startupsettings/writer.go b/ee/agent/startupsettings/writer.go
index 154d0d6b2..4c6105346 100644
--- a/ee/agent/startupsettings/writer.go
+++ b/ee/agent/startupsettings/writer.go
@@ -12,7 +12,6 @@ import (
 	"github.com/kolide/launcher/ee/agent/flags/keys"
 	agentsqlite "github.com/kolide/launcher/ee/agent/storage/sqlite"
 	"github.com/kolide/launcher/ee/agent/types"
-	"github.com/kolide/launcher/pkg/osquery"
 	"github.com/kolide/launcher/pkg/traces"
 )
 
@@ -101,7 +100,7 @@ func (s *startupSettingsWriter) Close() error {
 }
 
 func (s *startupSettingsWriter) extractAutoTableConstructionConfig() (string, error) {
-	osqConfig, err := s.knapsack.ConfigStore().Get([]byte(osquery.ConfigKey))
+	osqConfig, err := s.knapsack.ConfigStore().Get([]byte("config"))
 	if err != nil {
 		return "", fmt.Errorf("could not get osquery config from store: %w", err)
 	}
diff --git a/ee/agent/startupsettings/writer_test.go b/ee/agent/startupsettings/writer_test.go
index 6fa7fe21a..cf3167a42 100644
--- a/ee/agent/startupsettings/writer_test.go
+++ b/ee/agent/startupsettings/writer_test.go
@@ -12,7 +12,6 @@ import (
 	agentsqlite "github.com/kolide/launcher/ee/agent/storage/sqlite"
 	typesmocks "github.com/kolide/launcher/ee/agent/types/mocks"
 	"github.com/kolide/launcher/pkg/log/multislogger"
-	"github.com/kolide/launcher/pkg/osquery"
 	"github.com/stretchr/testify/mock"
 	"github.com/stretchr/testify/require"
 	_ "modernc.org/sqlite"
@@ -140,7 +139,7 @@ func TestFlagsChanged(t *testing.T) {
 	configJson, err := json.Marshal(configMap)
 	require.NoError(t, err, "marshalling config map")
 
-	configStore.Set([]byte(osquery.ConfigKey), configJson)
+	configStore.Set([]byte("config"), configJson)
 	k.On("ConfigStore").Return(configStore)
 
 	// Set up storage db, which should create the database and set all flags
diff --git a/pkg/osquery/extension.go b/pkg/osquery/extension.go
index 7e41d3143..631937a3c 100644
--- a/pkg/osquery/extension.go
+++ b/pkg/osquery/extension.go
@@ -15,6 +15,7 @@ import (
 
 	"github.com/google/uuid"
 	"github.com/kolide/launcher/ee/agent"
+	"github.com/kolide/launcher/ee/agent/startupsettings"
 	"github.com/kolide/launcher/ee/agent/types"
 	"github.com/kolide/launcher/pkg/backoff"
 	"github.com/kolide/launcher/pkg/osquery/runtime/history"
@@ -51,7 +52,7 @@ const (
 	// DB key for node key
 	nodeKeyKey = "nodeKey"
 	// DB key for last retrieved config
-	ConfigKey = "config"
+	configKey = "config"
 	// DB keys for the rsa keys
 	privateKeyKey = "privateKey"
 
@@ -332,7 +333,7 @@ func NodeKey(getter types.Getter) (string, error) {
 
 // Config returns the device config from the storage layer
 func Config(getter types.Getter) (string, error) {
-	key, err := getter.Get([]byte(ConfigKey))
+	key, err := getter.Get([]byte(configKey))
 	if err != nil {
 		return "", fmt.Errorf("error getting config key: %w", err)
 	}
@@ -504,7 +505,7 @@ func (e *Extension) GenerateConfigs(ctx context.Context) (map[string]string, err
 		)
 		// Try to use cached config
 		var confBytes []byte
-		confBytes, _ = e.knapsack.ConfigStore().Get([]byte(ConfigKey))
+		confBytes, _ = e.knapsack.ConfigStore().Get([]byte(configKey))
 
 		if len(confBytes) == 0 {
 			if !e.enrolled() {
@@ -516,7 +517,19 @@ func (e *Extension) GenerateConfigs(ctx context.Context) (map[string]string, err
 		config = string(confBytes)
 	} else {
 		// Store good config
-		e.knapsack.ConfigStore().Set([]byte(ConfigKey), []byte(config))
+		e.knapsack.ConfigStore().Set([]byte(configKey), []byte(config))
+
+		// open the start up settings writer just to trigger a write of the config,
+		// then we can immediately close it
+		startupSettingsWriter, err := startupsettings.OpenWriter(ctx, e.knapsack)
+		if err != nil {
+			e.slogger.Log(ctx, slog.LevelWarn,
+				"could not get startup settings writer",
+				"err", err,
+			)
+		} else {
+			startupSettingsWriter.Close()
+		}
 		// TODO log or record metrics when caching config fails? We
 		// would probably like to return the config and not an error in
 		// this case.
diff --git a/pkg/osquery/interactive/interactive.go b/pkg/osquery/interactive/interactive.go
index ae2257ec7..7506d26a8 100644
--- a/pkg/osquery/interactive/interactive.go
+++ b/pkg/osquery/interactive/interactive.go
@@ -61,7 +61,7 @@ func StartProcess(slogger *slog.Logger, rootDir, osquerydPath string, osqueryFla
 	// if we were not provided a config path flag, try to add default config
 	if !haveConfigPathOsqFlag {
 		// check to see if we can actually get a config plugin
-		configPlugin, err := configPlugin()
+		configPlugin, err := generateConfigPlugin()
 		if err != nil {
 			slogger.Log(context.TODO(), slog.LevelDebug,
 				"error creating config plugin",
@@ -189,7 +189,7 @@ func waitForFile(path string, interval, timeout time.Duration) error {
 	}
 }
 
-func configPlugin() (*config.Plugin, error) {
+func generateConfigPlugin() (*config.Plugin, error) {
 	r, err := startupsettings.OpenReader(context.TODO(), launcher.DefaultPath(launcher.RootDirectory))
 	if err != nil {
 		return nil, fmt.Errorf("error opening startup settings reader: %w", err)