I understand that session ids generated by tomcat are unique and fairly random. However I am wondering if that is true between tomcat restarts i.e. Is their any possibility that same session id is generated again after server is restarted ?
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As per @stdunbar, the same session id will not be regenerated after a server restart.
However, you need to be aware that Tomcat will save existing sessions to disk during an orderly shutdown and reload them when the server is restarted.
Therefore you may see the same session ids between restarts, but they will belong to the same client.