I just tried the run-on-pypy branch.  It doesn't segfault pypy on import, but none of the tests pass.

elf@linux640:/tmp$ /opt/pypy-1.4/bin/pypy `which trial` OpenSSL.test.test_crypto
OpenSSL.test.test_crypto
  FunctionTests
    test_dump_certificate ... RPython traceback:
  File "implement.c", line 199776, in _PyObject_New
  File "implement.c", line 241951, in _PyObject_NewVar
  File "implement.c", line 179834, in from_ref
  File "implement_4.c", line 132364, in CpyTypedescr_type_realize
  File "implement_1.c", line 44168, in type_realize
  File "implement_1.c", line 123481, in W_PyCTypeObject___init__
  File "implement.c", line 179783, in from_ref
Fatal RPython error: AssertionError
Aborted
elf@linux640:/tmp$ /opt/pypy-1.4/bin/pypy `which trial` OpenSSL.test.test_rand
OpenSSL.test.test_rand
  RandTests
    test_add ...                                                        [ERROR]
    test_bytes ...                                                      [ERROR]
    test_files ...                                                      [ERROR]
    test_seed ...                                                       [ERROR]
    test_status ...                                                     [ERROR]

===============================================================================
[ERROR]
Traceback (most recent call last):
  File "/opt/pypy-latest/lib-python/2.5.2/unittest.py", line 270, in run
    self.tearDown()
  File "/opt/pypy-latest/site-packages/OpenSSL/test/util.py", line 37, in tearDown
    _exception_from_error_queue()
OpenSSL.SSL.Error: []

OpenSSL.test.test_rand.RandTests.test_add
OpenSSL.test.test_rand.RandTests.test_bytes
OpenSSL.test.test_rand.RandTests.test_files
OpenSSL.test.test_rand.RandTests.test_seed
OpenSSL.test.test_rand.RandTests.test_status
-------------------------------------------------------------------------------
Ran 5 tests in 0.206s

FAILED (errors=5)
elf@linux640:/tmp$ /opt/pypy-1.4/bin/pypy `which trial` OpenSSL.test.test_ssl
OpenSSL.test.test_ssl
  ConnectionTests
    test_get_context ...                                                [ERROR]
                                               [ERROR]
    test_get_context_wrong_args ...                                     [ERROR]
                                    [ERROR]
    test_type ...                                                       [ERROR]
                                                      [ERROR]
  ConstantsTests
    test_op_cookie_exchange ...                                         [ERROR]
    test_op_no_query_mtu ...                                            [ERROR]
    test_op_no_ticket ...                                               [ERROR]
  ContextTests
    test_add_extra_chain_cert ...                                       [ERROR]
                                      [ERROR]
    test_add_extra_chain_cert_invalid_cert ...                          [ERROR]
                         [ERROR]
    test_load_verify_directory ...                                      [ERROR]
                                     [ERROR]
    test_load_verify_file ...                                           [ERROR]
                                          [ERROR]
    test_load_verify_invalid_file ...                                   [ERROR]
                                  [ERROR]
    test_method ...                                                     [ERROR]
                                                    [ERROR]
    test_set_default_verify_paths ...                                   [ERROR]
                                  [ERROR]
    test_set_default_verify_paths_signature ...                         [ERROR]
                        [ERROR]
    test_set_info_callback ...                                          [ERROR]
                                         [ERROR]
    test_set_passwd_cb ...                                              [ERROR]
                                             [ERROR]
    test_type ...                                                       [ERROR]
                                                      [ERROR]
    test_use_privatekey ...                                             [ERROR]
                                            [ERROR]
  ErrorTests
    test_type ...                                                       [ERROR]
  MemoryBIOTests
    test_add_client_ca_errors ...                                       [ERROR]
                                      [ERROR]
    test_memoryConnect ...                                              [ERROR]
                                             [ERROR]
    test_multiple_add_client_ca ...                                     [ERROR]
                                    [ERROR]
    test_mutated_ca_list ...                                            [ERROR]
                                           [ERROR]
    test_one_add_client_ca ...                                          [ERROR]
                                         [ERROR]
    test_outgoingOverflow ... Segmentation fault