I see this happen most often when a session tracking variable or critical parameter is not included in the recording for one reason or another.
Most commonly, the JSESSIONID or other custom, app-specific parameters to a request causes the server to return either a 400 (bad request) or 500 (internal server error) because it does not understand the request without proper parameters. Many times, a "context expired" SSL related message means that the server sent either no data or a partial error message back to the client because it did not provide the proper session or parameters in the request.
It is often resolved by going back and examining what was [not] posted in the specific request. If you right-click the failed message log item and select 'open associated request in editor...', then look at the Request > Form > Parameters and other related components of the request, it may be posting static values that need to be dynamic for the server to respond successfully.
Once you parameterize or adjust your request and then replay, make sure to have the Tools > Options > Engine > Simulation > "Store request bodies" preference enabled before you re-run the test. Now go back to the original request that was erroring out to see what's actually being posted. If your adjustment corrected the issue, you should no longer receive this error message.
