diff --git a/server/install.go b/server/install.go
index e72555e..fe0fcea 100644
--- a/server/install.go
+++ b/server/install.go
@@ -447,6 +447,14 @@ func (ip *InstallationProcess) Execute() (string, error) {
 		NetworkMode: container.NetworkMode(config.Get().Docker.Network.Mode),
 	}
 
+	// Ensure the root directory for the server exists properly before attempting
+	// to trigger the reinstall of the server. It is possible the directory would
+	// not exist when this runs if Wings boots with a missing directory and a user
+	// triggers a reinstall before trying to start the server.
+	if err := ip.Server.EnsureDataDirectoryExists(); err != nil {
+		return "", err
+	}
+
 	ip.Server.Log().WithField("install_script", ip.tempDir()+"/install.sh").Info("creating install container for server process")
 	// Remove the temporary directory when the installation process finishes for this server container.
 	defer func() {