diff --git a/x-pack/elastic-agent/CHANGELOG.asciidoc b/x-pack/elastic-agent/CHANGELOG.asciidoc
index b41651723c75..3a888c26442b 100644
--- a/x-pack/elastic-agent/CHANGELOG.asciidoc
+++ b/x-pack/elastic-agent/CHANGELOG.asciidoc
@@ -37,6 +37,7 @@
 - Fix reloading of log level for services {pull}[24055]24055
 - Fix: Successfully installed and enrolled agent running standalone{pull}[24128]24128
 - Make installer atomic on windows {pull}[24253]24253
+- Fix windows installer during enroll {pull}[24343]24343
 - Fix failing installation on windows 7 {pull}[24387]24387
 - Fix capabilities resolution in inspect command {pull}[24346]24346
 
diff --git a/x-pack/elastic-agent/pkg/artifact/install/atomic/atomic_installer.go b/x-pack/elastic-agent/pkg/artifact/install/atomic/atomic_installer.go
index 980bb2127f9d..60c5f1d28cfd 100644
--- a/x-pack/elastic-agent/pkg/artifact/install/atomic/atomic_installer.go
+++ b/x-pack/elastic-agent/pkg/artifact/install/atomic/atomic_installer.go
@@ -52,6 +52,21 @@ func (i *Installer) Install(ctx context.Context, spec program.Spec, version, ins
 		os.RemoveAll(tempInstallDir)
 	}
 
+	// on windows rename is not atomic, let's force it to flush the cache
+	defer func() {
+		if runtime.GOOS == "windows" {
+			if f, err := os.OpenFile(installDir, os.O_RDWR, 0777); err == nil {
+				f.Sync()
+				f.Close()
+			}
+
+			if f, err := os.OpenFile(tempInstallDir, os.O_RDWR, 0777); err == nil {
+				f.Sync()
+				f.Close()
+			}
+		}
+	}()
+
 	if err := i.installer.Install(ctx, spec, version, tempInstallDir); err != nil {
 		// cleanup unfinished install
 		if rerr := os.RemoveAll(tempInstallDir); rerr != nil {
@@ -70,12 +85,5 @@ func (i *Installer) Install(ctx context.Context, spec program.Spec, version, ins
 		return err
 	}
 
-	// on windows rename is not atomic, let's force it to flush the cache
-	if runtime.GOOS == "windows" {
-		if f, err := os.OpenFile(installDir, os.O_SYNC|os.O_RDWR, 0755); err == nil {
-			f.Sync()
-		}
-	}
-
 	return nil
 }
diff --git a/x-pack/elastic-agent/pkg/artifact/install/zip/zip_installer.go b/x-pack/elastic-agent/pkg/artifact/install/zip/zip_installer.go
index 3073da25ca40..034e4be7b416 100644
--- a/x-pack/elastic-agent/pkg/artifact/install/zip/zip_installer.go
+++ b/x-pack/elastic-agent/pkg/artifact/install/zip/zip_installer.go
@@ -69,7 +69,7 @@ func (i *Installer) Install(ctx context.Context, spec program.Spec, version, ins
 	return nil
 }
 
-func (i *Installer) unzip(ctx context.Context, artifactPath string) error {
+func (i *Installer) unzip(_ context.Context, artifactPath string) error {
 	r, err := zip.OpenReader(artifactPath)
 	if err != nil {
 		return err
@@ -120,11 +120,6 @@ func (i *Installer) unzip(ctx context.Context, artifactPath string) error {
 	}
 
 	for _, f := range r.File {
-		// if we were cancelled in between
-		if err := ctx.Err(); err != nil {
-			return err
-		}
-
 		if err := unpackFile(f); err != nil {
 			return err
 		}