Generally, an insurance agent owes only a regular agent’s duties of reasonable care, diligence, and judgment in procuring the insurance requested by an insured. However, an insurance agent may assume a greater duty to the insured when one of the following three exceptions arise: “(a) the agent misrepresents the nature, extent or scope of the coverage being offered or provided, (b) there is a request or inquiry by the insured for a particular type or extent of coverage, or (c) the agent assumes an additional duty by either express agreement or by ‘holding himself out’ as having expertise in a given field of insurance being sought by the insured.’ This decision holds that evidence of specialization at a minimum creates a presumption the agent/broker anticipates their clients will rely on their acknowledged expertise and supports courts imposing an extended duty. Here, the insured raised at least a triable issue of fact as to whether UPS’ subsidiary insurance agency was sufficiently specialized in inland marine insurance for UPS shipments that it had a duty to explain the dense, confusing language of the policy it sold to the insured which turned out not to cover the type of loss most likely to (and which did) occur to his cargo.