Hmm maybe the sessionId cookie gets lost somehow during the test? Can you 
verify that the first request creates a session on the server and the 
response contains a Set-Cookie header with the sessionId? Finally the 
second request should send that sessionId cookie to the server otherwise a 
new session will be created again.

Does it work when you launch your GWT tests using the JVM parameter:

-Dgwt.args="-prod -runStyle Manual:1"

and then visit the provided URL in a browser? That basically compiles your 
GWT test module to JavaScript and lets you execute the tests in a browser.

-- J.

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