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Explore advanced offensive strategies used by adversaries to penetrate the OT DMZ and pivot into sensitive operational technology control systems in this 17-minute conference talk from DEF CON 33. Learn how misconfigured remote access solutions, poorly segmented architectures, and legacy services create exploitable pathways into industrial environments through real-world red team operations and threat intelligence insights. Discover practical tactics, techniques, and procedures (TTPs) for identifying and abusing jump hosts, proxy services, Citrix gateways, and RDP relays to achieve lateral movement from enterprise footholds into OT networks. Examine methods for credential access and evasion within the DMZ layer while understanding how common assumptions about network segmentation often fail in practice. Gain defensive insights to help detect and mitigate these threats before they escalate, with content specifically designed for offensive security professionals, defenders, and industrial security leaders who need to understand current OT perimeter targeting methods and protection strategies.