The initialization of DTLS uses the s->server member which is not set correctly.

--
Index: ssl/ssl_lib.c
===================================================================
RCS file: /v/openssl/cvs/openssl/ssl/ssl_lib.c,v
retrieving revision 1.172
diff -u -r1.172 ssl_lib.c
--- ssl/ssl_lib.c       4 Aug 2008 22:10:38 -0000       1.172
+++ ssl/ssl_lib.c       15 Sep 2008 11:36:46 -0000
@@ -358,12 +358,12 @@

        s->method=ctx->method;

-       if (!s->method->ssl_new(s))
-               goto err;
-
        s->references=1;
        s->server=(ctx->method->ssl_accept == ssl_undefined_function)?0:1;

+       if (!s->method->ssl_new(s))
+               goto err;
+
        SSL_clear(s);

        CRYPTO_new_ex_data(CRYPTO_EX_INDEX_SSL, s, &s->ex_data);
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