diff --git a/cmd/cli/commands/run/run.go b/cmd/cli/commands/run/run.go
index 5211bf8..45335ab 100644
--- a/cmd/cli/commands/run/run.go
+++ b/cmd/cli/commands/run/run.go
@@ -124,7 +124,7 @@ func archiveIfChanged(gameID, srcDir, destTarGz, stateFile string) error {
 	defer f.Close()
 
 	if err := archive.Tar(f, srcDir); err != nil {
-		return fmt.Errorf("failed archiving files")
+		return fmt.Errorf("failed archiving files: %w", err)
 	}
 
 	now := time.Now().UTC().Format(time.RFC3339)
diff --git a/pkg/tools/archive/archive.go b/pkg/tools/archive/archive.go
index b3a6b7d..0ebef41 100644
--- a/pkg/tools/archive/archive.go
+++ b/pkg/tools/archive/archive.go
@@ -83,23 +83,23 @@ func Tar(file io.Writer, root string) error {
 	// Walk again to add files
 	err := filepath.Walk(root, func(path string, info os.FileInfo, walkErr error) error {
 		if walkErr != nil {
-			return walkErr
+			return fmt.Errorf("failed to walk through the directory: %w", walkErr)
 		}
 
-		path, err := filepath.Rel(root, path)
+		relpath, err := filepath.Rel(root, path)
 		if err != nil {
-			return err
+			return fmt.Errorf("failed to make relative path: %w", err)
 		}
 
 		// Create tar header
 		header, err := tar.FileInfoHeader(info, path)
 		if err != nil {
-			return err
+			return fmt.Errorf("failed to make file info header: %w", err)
 		}
-		header.Name = path
+		header.Name = relpath
 
 		if err := tw.WriteHeader(header); err != nil {
-			return err
+			return fmt.Errorf("failed to write header: %w", err)
 		}
 
 		if !info.Mode().IsRegular() {
@@ -108,11 +108,11 @@ func Tar(file io.Writer, root string) error {
 
 		file, err := os.Open(path)
 		if err != nil {
-			return err
+			return fmt.Errorf("failed to open file: %w", err)
 		}
 		defer file.Close()
 		if _, err := io.Copy(tw, file); err != nil {
-			return err
+			return fmt.Errorf("failed to copy file: %w", err)
 		}
 		return nil
 	})