Three authentication methods are proposed by the JIRA REST API documentation: Basic Authentication is a simple but not very safe approach. Credentials are sent in the header on every request and encoding to Base64 is not a proper protection in this case; HTTPS connection is required. OAuth authentication - looks a bit complex and requires additional configuration at the JIRA server that is not always possible. Cookie-based Authentication - this approach seems to be the most convinient one: credentials are checked once, then the authentication cookie only is sent on subsequent requests. However, trying to use the cookie-based authentication I encountered an issue. The approach described in the documentation worked partially: I was able to create a new session and get the response containing the session cookie but all subsequent requests using this session cookie were rejected as unauthorized. Spending some time investigating this I found the cause of the issue: JSESSIO...