Is SkyWatch an insurance company? SkyWatch.AI Support 25 December 2019 11:33 Updated Follow SkyWatch is a licensed insurance producer (agent). Our policies are underwritten by Chaucer, A Lloyd's syndicate. Related articles How does SkyWatch.AI's policy compare to a traditional policy through a broker? Who is the insurance underwriter/carrier? Does SkyWatch.AI allow flight planning or just insurance? How can I contact SkyWatch.AI? Where is SkyWatch.AI insurance active? Comments 0 comments Article is closed for comments.