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Flawed TLS certificates are not uncommon on the Internet. While they signal apotential issue, in most cases they have benign causes (e.g., misconfigurationor even deliberate deployment). This adds fuzziness to the decision on whetherto trust a connection or not. Little is known about perceptions of flawedcertificates by IT professionals, even though their decisions impact highnumbers of end users. Moreover, it is unclear how much the content of errormessages and documentation influences these perceptions. To shed light on theseissues, we observed 75 attendees of an industrial IT conference investigatingdifferent certificate validation errors. We also analyzed the influence ofreworded error messages and redesigned documentation. We find that peopleworking in IT have very nuanced opinions, with trust decisions being far frombinary. The self-signed and the name-constrained certificates seem to beover-trusted (the latter also being poorly understood). We show that even smallchanges in existing error messages can positively influence resource use,comprehension, and trust assessment. At the end of the article, we summarizelessons learned from conducting usable security studies with IT professionals.

Will You Trust This TLS Certificate? Perceptions of People Working in IT (Extended Version)