Advances like Industry 4.0 lead to a rising number of Internet-connected industrial deployments and thus an Industrial Internet of Things with growing attack vectors. To uphold a secure and safe operation of these deployments, industrial protocols nowadays include security features, e.g., end-to-end secure communication. However, so far, it is unclear how well these features are used in practice and which obstacles might prevent operators from securely running their deployments. In this research description paper, we summarize our recent research activities to close this gap. Specifically, we show that even secure-by-design protocols are by far no guarantee for secure deployments. Instead, many deployments still open the doors for eavesdropping attacks or malicious takeovers. Additionally, we give an outlook on how to overcome identified obstacles allowing operators to configure their deployments more securely.