This updated version includes the suggestions of Nagendra Modadugu.

--- ssl/d1_both.c       2007-10-17 23:17:49.000000000 +0200
+++ ssl/d1_both.c       2009-03-23 19:39:10.000000000 +0100
@@ -136,7 +136,6 @@
  static void dtls1_set_message_header_int(SSL *s, unsigned char mt,
        unsigned long len, unsigned short seq_num, unsigned long frag_off,
        unsigned long frag_len);
-static int dtls1_retransmit_buffered_messages(SSL *s);
  static long dtls1_get_message_fragment(SSL *s, int st1, int stn,
        long max, int *ok);

@@ -942,8 +941,21 @@
        return dtls1_retransmit_buffered_messages(s) ;
        }

+int
+dtls1_get_queue_priority(unsigned short seq, int is_ccs)
+       {
+       /* The index of the retransmission queue actually is the message  
sequence number,
+        * since the queue only contains messages of a single handshake.  
However, the
+        * ChangeCipherSpec has no message sequence number and so using only  
the sequence
+        * will result in the CCS and Finished having the same index. To  
prevent this,
+        * the sequence number is multiplied by 2. In case of a CCS 1 is  
subtracted.
+        * This does not only differ CSS and Finished, it also maintains the  
order of the
+        * index (important for priority queues) and fits in the unsigned  
short variable.
+        */     
+       return seq * 2 - is_ccs;
+       }

-static int
+int
  dtls1_retransmit_buffered_messages(SSL *s)
        {
        pqueue sent = s->d1->sent_messages;
@@ -957,8 +969,9 @@
        for ( item = pqueue_next(&iter); item != NULL; item =  
pqueue_next(&iter))
                {
                frag = (hm_fragment *)item->data;
-               if ( dtls1_retransmit_message(s, frag->msg_header.seq, 0, 
&found)  
<= 0 &&
-                       found)
+                       if ( dtls1_retransmit_message(s,
+                               dtls1_get_queue_priority(frag->msg_header.seq, 
frag- 
 >msg_header.is_ccs),
+                               0, &found) <= 0 && found)
                        {
                        fprintf(stderr, "dtls1_retransmit_message() failed\n");
                        return -1;
@@ -974,7 +987,6 @@
        pitem *item;
        hm_fragment *frag;
        PQ_64BIT seq64;
-       unsigned int epoch = s->d1->w_epoch;

        /* this function is called immediately after a message has
         * been serialized */
@@ -988,7 +1000,6 @@
                {
                OPENSSL_assert(s->d1->w_msg_hdr.msg_len +
                        DTLS1_CCS_HEADER_LENGTH <= (unsigned int)s->init_num);
-               epoch++;
                }
        else
                {
@@ -1003,9 +1014,19 @@
        frag->msg_header.frag_len = s->d1->w_msg_hdr.msg_len;
        frag->msg_header.is_ccs = is_ccs;

+       /* save current state*/
+       frag->msg_header.saved_retransmit_state.enc_write_ctx = s- 
 >enc_write_ctx;
+       frag->msg_header.saved_retransmit_state.write_hash = s->write_hash;
+       frag->msg_header.saved_retransmit_state.compress = s->compress;
+       frag->msg_header.saved_retransmit_state.session = s->session;
+       frag->msg_header.saved_retransmit_state.epoch = s->d1->w_epoch;
+
        pq_64bit_init(&seq64);
-       pq_64bit_assign_word(&seq64, epoch<<16 | frag->msg_header.seq);

+       pq_64bit_assign_word(&seq64,
+                                                
dtls1_get_queue_priority(frag->msg_header.seq,
+                                                                               
                  frag->msg_header.is_ccs));
+               
        item = pitem_new(seq64, frag);
        pq_64bit_free(&seq64);
        if ( item == NULL)
@@ -1034,6 +1055,8 @@
        hm_fragment *frag ;
        unsigned long header_length;
        PQ_64BIT seq64;
+       struct dtls1_retransmit_state saved_state;
+       unsigned char save_write_sequence[8];

        /*
          OPENSSL_assert(s->init_num == 0);
@@ -1069,9 +1092,45 @@
                frag->msg_header.msg_len, frag->msg_header.seq, 0,
                frag->msg_header.frag_len);

+       /* save current state */
+       saved_state.enc_write_ctx = s->enc_write_ctx;
+       saved_state.write_hash = s->write_hash;
+       saved_state.compress = s->compress;
+       saved_state.session = s->session;
+       saved_state.epoch = s->d1->w_epoch;
+       saved_state.epoch = s->d1->w_epoch;
+       
        s->d1->retransmitting = 1;
+       
+       /* restore state in which the message was originally sent */
+       s->enc_write_ctx = frag- 
 >msg_header.saved_retransmit_state.enc_write_ctx;
+       s->write_hash = frag->msg_header.saved_retransmit_state.write_hash;
+       s->compress = frag->msg_header.saved_retransmit_state.compress;
+       s->session = frag->msg_header.saved_retransmit_state.session;
+       s->d1->w_epoch = frag->msg_header.saved_retransmit_state.epoch;
+       
+       if (frag->msg_header.saved_retransmit_state.epoch ==  
saved_state.epoch - 1)
+       {
+               memcpy(save_write_sequence, s->s3->write_sequence, 
sizeof(s->s3- 
 >write_sequence));
+               memcpy(s->s3->write_sequence, s->d1->last_write_sequence, 
sizeof(s- 
 >s3->write_sequence));
+       }
+       
        ret = dtls1_do_write(s, frag->msg_header.is_ccs ?
-               SSL3_RT_CHANGE_CIPHER_SPEC : SSL3_RT_HANDSHAKE);
+                                                SSL3_RT_CHANGE_CIPHER_SPEC : 
SSL3_RT_HANDSHAKE);
+       
+       /* restore current state */
+       s->enc_write_ctx = saved_state.enc_write_ctx;
+       s->write_hash = saved_state.write_hash;
+       s->compress = saved_state.compress;
+       s->session = saved_state.session;
+       s->d1->w_epoch = saved_state.epoch;
+       
+       if (frag->msg_header.saved_retransmit_state.epoch ==  
saved_state.epoch - 1)
+       {
+               memcpy(s->d1->last_write_sequence, s->s3->write_sequence, 
sizeof(s- 
 >s3->write_sequence));
+               memcpy(s->s3->write_sequence, save_write_sequence, 
sizeof(s->s3- 
 >write_sequence));
+       }
+
        s->d1->retransmitting = 0;

        (void)BIO_flush(SSL_get_wbio(s));
--- ssl/d1_pkt.c        2008-10-13 08:43:06.000000000 +0200
+++ ssl/d1_pkt.c        2009-03-23 19:45:04.000000000 +0100
@@ -942,7 +942,9 @@
                                n2s(p, seq);
                                n2l3(p, frag_off);

-                               dtls1_retransmit_message(s, seq, frag_off, 
&found);
+                               dtls1_retransmit_message(s,
+                                                                               
 dtls1_get_queue_priority(frag->msg_header.seq, 0),
+                                                                               
 frag_off, &found);
                                if ( ! found  && SSL_in_init(s))
                                        {
                                        /* fprintf( stderr,"in init = %d\n", 
SSL_in_init(s)); */
@@ -1035,6 +1037,16 @@
                        goto start;
                        }

+               /* If we are server, we may have a repeated FINISHED of the
+                * client here, then retransmit our CCS and FINISHED.
+                */
+               if (msg_hdr.type == SSL3_MT_FINISHED)
+                       {
+                       dtls1_retransmit_buffered_messages(s);
+                       rr->length = 0;
+                       goto start;
+                       }
+
                if (((s->state&SSL_ST_MASK) == SSL_ST_OK) &&
                        !(s->s3->flags & SSL3_FLAGS_NO_RENEGOTIATE_CIPHERS))
                        {
@@ -1758,6 +1770,7 @@
        else
                {
                seq = s->s3->write_sequence;
+               memcpy(s->d1->last_write_sequence, seq, sizeof(s->s3- 
 >write_sequence));
                s->d1->w_epoch++;
                }

--- ssl/dtls1.h 2008-09-13 20:25:36.000000000 +0200
+++ ssl/dtls1.h 2009-03-23 19:31:39.000000000 +0100
@@ -101,6 +101,19 @@
        PQ_64BIT max_seq_num;  /* max record number seen so far */
        } DTLS1_BITMAP;

+struct dtls1_retransmit_state
+       {
+       EVP_CIPHER_CTX *enc_write_ctx;  /* cryptographic state */
+       const EVP_MD *write_hash;               /* used for mac generation */
+#ifndef OPENSSL_NO_COMP
+       COMP_CTX *compress;                             /* compression */
+#else
+       char *compress; 
+#endif
+       SSL_SESSION *session;
+       unsigned short epoch;
+       };
+
  struct hm_header_st
        {
        unsigned char type;
@@ -109,6 +122,7 @@
        unsigned long frag_off;
        unsigned long frag_len;
        unsigned int is_ccs;
+       struct dtls1_retransmit_state saved_retransmit_state;
        };

  struct ccs_header_st
@@ -168,6 +182,9 @@

        unsigned short handshake_read_seq;

+       /* save last sequence number for retransmissions */
+       unsigned char last_write_sequence[8];
+
        /* Received handshake records (processed and unprocessed) */
        record_pqueue unprocessed_rcds;
        record_pqueue processed_rcds;
--- ssl/ssl_locl.h      2009-01-05 15:43:07.000000000 +0100
+++ ssl/ssl_locl.h      2009-03-23 19:42:12.000000000 +0100
@@ -862,6 +862,8 @@
  int dtls1_buffer_message(SSL *s, int ccs);
  int dtls1_retransmit_message(SSL *s, unsigned short seq,
        unsigned long frag_off, int *found);
+int dtls1_get_queue_priority(unsigned short seq, int is_ccs);
+int dtls1_retransmit_buffered_messages(SSL *s);
  void dtls1_clear_record_buffer(SSL *s);
  void dtls1_get_message_header(unsigned char *data, struct  
hm_header_st *msg_hdr);
  void dtls1_get_ccs_header(unsigned char *data, struct ccs_header_st  
*ccs_hdr);




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