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2009 - Null prefix attack
Moxie Marlinspike gets a certificate from ipsCA for a DNS name containing a null character. Although ipsCA correctly validates the DNS name as belonging to Moxie's domain, the null character tricks some clients into thinking the certificate belongs to www.paypal.com, enabling impersonation of PayPal.
Root cause: TLS clients were only comparing DNS names up to the first null character instead of in their entirety. ipsCA was allowing null characters in DNS names despite this being a violation of X.509 standards.
Cert Spotter detects null prefix attacks and alerts the owner of the domain being targeted.
2011 - Comodo
An attacker by the alias "Comodohacker" compromises several Comodo resellers and obtains rogue certificates for www.google.com, mail.google.com, addons.mozilla.org, login.live.com, login.yahoo.com, and login.skype.com.
Root cause: Comodo was trusting resellers to perform domain control validation, which is a critical certificate authority function, instead of doing it themselves.
2011 - DigiNotar
An unknown attacker completely compromises DigiNotar and after obtaining full administrative access to all critical CA systems, issues rogue certificates for numerous domains. Over 500 fake certificates are detected, but the full extent of the breach remains unknown. A rogue wildcard certificate for google.com is used for mass interception of traffic from Iranian citizens.
Root cause: Insufficient network segmentation and generally poor security practices allowed the attacker to completely compromise DigiNotar after exploiting a vulnerability in a publicly-facing web server running out-of-date software.
DigiNotar is quickly distrusted by all major platforms.
2011 - TurkTrust
TurkTrust accidentally issues two intermediate CA certificates to subscribers. These intermediate certificates can be used to forge certificates for any domain on the Internet. Sixteen months later, one of them is used to forge a certificate for google.com.
Root cause: TurkTrust mistakenly applied a security policy from their test environment to their production environment, causing unconstrained intermediate CA certificates to be issued instead of regular end-entity certificates.
2014 - NICCA
The National Informatics Centre (NIC) of India, a subordinate CA of the Indian Controller of Certifying Authorities (India CCA), issues rogue certificates for Google and Yahoo domains. NIC claims that their issuance process was compromised and that only four certificates were misissued. However, Google is aware of misissued certificates not reported by NIC, so it can only be assumed that the scope of the breach is unknown.
Root cause: Compromise of certificate authority, with unknown scope.
2015 - CNNIC
CNNIC, in violation of their certificate practice statement, willfully issues an unconstrained intermediate CA certificate to MCS Holdings, an organization with no certificate practice statement or technical infrastructure whatsoever to operate a certificate authority. MCS Holdings uses the intermediate CA to forge certificates for Google and likely other domains.
Root cause: CNNIC violated their certificate practice statement and failed to properly oversee the practices of their subordinate certificate authorities.
CNNIC is distrusted by browsers.
2015 - WoSign
A researcher discovers that WoSign will perform domain control validation via unprivileged TCP ports and uses this to obtain an unauthorized certificate for a university. Despite being informed of the misissuance, WoSign fails to notify web browsers and the incident is not noted in WoSign's annual audit. It will not be publicly disclosed until a year later.
Root cause: WoSign was allowing unprivileged TCP ports (1024 and above) to be used for domain control validation. Since non-administrative users are typically allowed to accept connections on unprivileged TCP ports, this allowed users to obtain certificates for domains they did not administer.
Initially, WoSign announces that all certificates they issue will be logged to Certificate Transparency logs, but they are ultimately distrusted by all major platforms due to their malfeasance.
https://sslmate.com/certspotter/failures