Silverstripe CMS sites through 4.4.4 which have opted into HTTP Cache Headers on responses served by the framework's HTTP layer can be vulnerable to web cache poisoning. Through modifying the X-Original-Url and X-HTTP-Method-Override headers, responses with malicious HTTP headers can return unexpected responses to other consumers of this cached response. Most other headers associated with web cache poisoning are already disabled through request hostname forgery whitelists.
In the Versioned Files module through 2.0.3 for SilverStripe 3.x, unpublished versions of files are publicly exposed to anyone who can guess their URL. This guess could be highly informed by a basic understanding of the symbiote/silverstripe-versionedfiles source code. (Users who upgrade from SilverStripe 3.x to 4.x and had Versioned Files installed have no further need for this module, because the 4.x release has built-in versioning. However, nothing in the upgrade process automates the destruction of these insecure artefacts, nor alerts the user to the criticality of destruction.)
SilverStripe through 4.3.3 has incorrect access control for protected files uploaded via Upload::loadIntoFile(). An attacker may be able to guess a filename in silverstripe/assets via the AssetControlExtension.