If I recall correctly, when I saw this problem the issue was sending user data larger than the MTU detected during handshake negotiation. The DTLS code seems to have some inconsistencies related to this, as MTU should not have an effect on user data -- the protocol only provides fragmentation of handshakes.

 - Ariel

Joel Reardon via RT wrote:
For version 0.9.8h
in do_dtls1_write()

in the block:

/* first check if there is a SSL3_BUFFER still being written
  * out.  This will happen with non blocking IO */
if (s->s3->wbuf.left != 0)
{
        OPENSSL_assert(0); /* XDTLS:  want to see if we ever get
here */
        return(ssl3_write_pending(s,type,buf,len));
}


To answer the comment's question: "Yes, we do get there."

Regards,
Joel Reardon

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- Ariel Salomon / Senior Software Engineer
Real-Time Innovations (RTI) / www.rti.com
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RTI - The Real-Time Middleware Experts


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