Modern day fraud looks different, partly due to technological change and the use of financialized entities in a changed regulatory environment which has removed many frictions that used to exist in business. Sometimes the victim is the direct author of its own loss, as with authorized push payment fraud. Often, this comes about because some form of deception has been practiced on the victim and so the issue is with gatekeeper liability, often for an omission. We now see the rediscovery of a common law duty based on failure to prevent fraud on the part of banks in the UK. This may be due to courts’ willingness to accept regulatory standards in deciding on facilitator liability, even if that may not have been the case in the past with respect to the more direct liability of financial institutions. Negligence may have to be understood in context, however, if liability is linked to external regulatory codes. But facilitators are not just entities themselves; often senior individuals in those entities can and must be incentivized to set up systems to prevent external wrongdoing or regulatory breaches. While they are usually insulated from liability to third parties, their duties to their company or entity must also be understood in context so that a proper chain of responsibility can be created. Regulatory changes provided new powers to decision makers but may have imposed duties on facilitators and we need to find the right framework to ensure that they are exercised properly and judged accordingly.