Penetration test reports commonly contain mention of vulnerabilities in SSL/TLS (hereafter referred to as just SSL). In many cases, this is due to system administrators not understanding the details of these services’ configuration and assuming that simply using SSL provides security. The issues identified during penetration tests are usually low in severity, as an average attacker would find them difficult to exploit, but they should be taken seriously to ensure that data in transit is properly secured. If something’s worth doing, it’s worth doing well. This whitepaper, co-written with Will Alexander, discusses how organisations can avoid SSL issues commonly found during penetration tests, ensure that data in transit is properly secured and ultimately instil in users a sense of confidence that their information is adequately protected.