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Are you sure the problem occurs during session resumption?
SSL version 2 hello was disabled by default on the client in JDK 7. If you want to use it, you will have to enable it by calling SSLSocket/SSLEngine.setProtocols() explicit.
Some older servers don't know what to do with unknown extensions. They are supposed to ignore them, but some actually close the connections with an error. By encapsulating, you are essentially stripping off any extensions because there is no such thing in the SSLv2 format. Suggest upgrading server if possible.