Flawed TLS certificates are not uncommon on the Internet. While they signal a potential issue, in most cases they have benign causes (e.g., misconfiguration or even deliberate deployment). This adds fuzziness to the decision on whether to trust a connection or not. Little is known about perceptions of flawed certificates by IT professionals, even though their decisions impact high numbers of end users. Moreover, it is unclear how much does the content of error messages and documentation influence these perceptions. To shed light on these issues, we observed 75 attendees of an industrial IT conference investigating different certificate validation errors. We also analysed the influence of re-worded error messages and redesigned documentation. We find that people working in IT have very nuanced opinions with trust decisions being far from binary. The self-signed and the name constrained certificates seem to be over-trusted (the latter also being poorly understood). We show that even small changes in existing error messages can positively influence resource use, comprehension, and trust assessment. Our re-worded error messages and documentation can be directly adopted.