https://github.com/spring-projects/spring-integration/blob/775bfd6168925c8fee94a22deec11ca84926550e/spring-integration-smb/src/main/java/org/springframework/integration/smb/session/SmbSession.java#L341 Hi, the method linked above checks the remote path (which is a smb path) for `FILE_SEPARATOR` which is initialized as ``` private static final String FILE_SEPARATOR = FileSystems.getDefault().getSeparator(); ``` Clearly on Windows that is "\\" which is never found in a smb path. So the need to create possibly missing remote dirs is never detected.