diff --git a/pkg/fleet/bootstraper/bootstraper.go b/pkg/fleet/bootstraper/bootstraper.go
index d9baa02992f80..e0404938a2883 100644
--- a/pkg/fleet/bootstraper/bootstraper.go
+++ b/pkg/fleet/bootstraper/bootstraper.go
@@ -20,6 +20,9 @@ import (
 const (
 	installerPackage = "datadog-installer"
 	installerBinPath = "bin/installer/installer"
+
+	hashFilePath = "/opt/datadog-installer/run/installer-hash"
+	rootTmpDir   = "/opt/datadog-installer/run"
 )
 
 // Option are the options for the bootstraper.
@@ -85,6 +88,7 @@ func WithSite(site string) Option {
 // 2. Export the installer image as an OCI layout on the disk.
 // 3. Extract the installer image layers on the disk.
 // 4. Run the installer from the extract layer with `install file://<layout-path>`.
+// 5. Write a file on the disk with the hash of the installed version.
 func Bootstrap(ctx context.Context, opts ...Option) error {
 	o := newOptions()
 	for _, opt := range opts {
@@ -101,9 +105,20 @@ func Bootstrap(ctx context.Context, opts ...Option) error {
 	if downloadedPackage.Name != installerPackage {
 		return fmt.Errorf("unexpected package name: %s, expected %s", downloadedPackage.Name, installerPackage)
 	}
+	hash, err := downloadedPackage.Image.Digest()
+	if err != nil {
+		return fmt.Errorf("failed to get image digest: %w", err)
+	}
+	existingHash, err := os.ReadFile(hashFilePath)
+	if err != nil && !os.IsNotExist(err) {
+		return fmt.Errorf("failed to read hash file: %w", err)
+	}
+	if string(existingHash) == hash.String() {
+		return nil
+	}
 
 	// 2. Export the installer image as an OCI layout on the disk.
-	layoutTmpDir, err := os.MkdirTemp("", "")
+	layoutTmpDir, err := os.MkdirTemp(rootTmpDir, "")
 	if err != nil {
 		return fmt.Errorf("failed to create temporary directory: %w", err)
 	}
@@ -114,7 +129,7 @@ func Bootstrap(ctx context.Context, opts ...Option) error {
 	}
 
 	// 3. Extract the installer image layers on the disk.
-	binTmpDir, err := os.MkdirTemp("", "")
+	binTmpDir, err := os.MkdirTemp(rootTmpDir, "")
 	if err != nil {
 		return fmt.Errorf("failed to create temporary directory: %w", err)
 	}
@@ -131,5 +146,11 @@ func Bootstrap(ctx context.Context, opts ...Option) error {
 	if err != nil {
 		return fmt.Errorf("failed to run installer: %w", err)
 	}
+
+	// 5. Write a file on the disk with the hash of the installed version.
+	err = os.WriteFile(hashFilePath, []byte(hash.String()), 0644)
+	if err != nil {
+		return fmt.Errorf("failed to write hash file: %w", err)
+	}
 	return nil
 }
diff --git a/test/new-e2e/tests/installer/linux_test.go b/test/new-e2e/tests/installer/linux_test.go
index 5a29e35668b16..1063bb0461de2 100644
--- a/test/new-e2e/tests/installer/linux_test.go
+++ b/test/new-e2e/tests/installer/linux_test.go
@@ -108,6 +108,7 @@ func TestSuseARM(t *testing.T) {
 }
 
 func (v *installerSuite) bootstrap(remoteUpdatesEnabled bool) {
+	v.Env().RemoteHost.MustExecute("sudo rm /opt/datadog-installer/run/installer-hash || true")
 	v.Env().RemoteHost.MustExecute(
 		"sudo -E datadog-bootstrap bootstrap",
 		client.WithEnvVariables(client.EnvVar{
@@ -227,6 +228,7 @@ func (v *installerSuite) TestExperimentCrash() {
 
 func (v *installerSuite) TestUninstall() {
 	host := v.Env().RemoteHost
+	v.bootstrap(false)
 
 	installAssertions := []string{
 		"test -d /opt/datadog-packages",