diff --git a/nsock/src/nsock_connect.c b/nsock/src/nsock_connect.c
index 93a43c94d..f2291676e 100644
--- a/nsock/src/nsock_connect.c
+++ b/nsock/src/nsock_connect.c
@@ -473,11 +473,14 @@ nsock_event_id nsock_connect_ssl(nsock_pool nsp, nsock_iod nsiod, nsock_ev_handl
   struct npool *ms = (struct npool *)nsp;
   struct nevent *nse;
 
-  if (!ms->sslctx)
+  if (proto == IPPROTO_UDP)
   {
-    if (proto == IPPROTO_UDP)
+    if (!ms->dtlsctx)
       nsock_pool_dtls_init(ms, 0);
-    else
+  }
+  else
+  {
+    if (!ms->sslctx)
       nsock_pool_ssl_init(ms, 0);
   }
 
@@ -523,6 +526,8 @@ nsock_event_id nsock_reconnect_ssl(nsock_pool nsp, nsock_iod nsiod, nsock_ev_han
   struct niod *nsi = (struct niod *)nsiod;
   struct npool *ms = (struct npool *)nsp;
   struct nevent *nse;
+  /* nsock_reconnect_ssl not supported for DTLS (yet?) */
+  assert(nsi->lastproto != IPPROTO_UDP);
 
   if (!ms->sslctx)
     nsock_pool_ssl_init(ms, 0);
diff --git a/nsock/src/nsock_core.c b/nsock/src/nsock_core.c
index 9f4f1bb30..411838fa8 100644
--- a/nsock/src/nsock_core.c
+++ b/nsock/src/nsock_core.c
@@ -340,6 +340,7 @@ void handle_connect_result(struct npool *ms, struct nevent *nse, enum nse_status
   int sslconnect_inprogress = nse->type == NSE_TYPE_CONNECT_SSL && nse->iod &&
     (nse->sslinfo.ssl_desire == SSL_ERROR_WANT_READ ||
      nse->sslinfo.ssl_desire == SSL_ERROR_WANT_WRITE);
+  SSL_CTX *sslctx = NULL;
 #else
   int sslconnect_inprogress = 0;
 #endif
@@ -366,11 +367,12 @@ void handle_connect_result(struct npool *ms, struct nevent *nse, enum nse_status
     if (nse->type == NSE_TYPE_CONNECT_SSL &&
         nse->status == NSE_STATUS_SUCCESS) {
 #if HAVE_OPENSSL
-      assert(ms->sslctx != NULL);
+      sslctx = iod->lastproto == IPPROTO_UDP ? ms->dtlsctx : ms->sslctx;
+      assert(sslctx != NULL);
       /* Reuse iod->ssl if present. If set, this is the second try at connection
          without the SSL_OP_NO_SSLv2 option set. */
       if (iod->ssl == NULL) {
-        iod->ssl = SSL_new(ms->sslctx);
+        iod->ssl = SSL_new(sslctx);
         if (!iod->ssl)
           fatal("SSL_new failed: %s", ERR_error_string(ERR_get_error(), NULL));
       }
diff --git a/nsock/src/nsock_internal.h b/nsock/src/nsock_internal.h
index 2dc59424a..e73502e97 100644
--- a/nsock/src/nsock_internal.h
+++ b/nsock/src/nsock_internal.h
@@ -202,6 +202,9 @@ struct npool {
 #if HAVE_OPENSSL
   /* The SSL Context (options and such) */
   SSL_CTX *sslctx;
+#ifdef HAVE_DTLS_CLIENT_METHOD
+  SSL_CTX *dtlsctx;
+#endif
 #endif
 
   /* Optional proxy chain (NULL is not set). Can only be set once per NSP (using
diff --git a/nsock/src/nsock_pool.c b/nsock/src/nsock_pool.c
index 095b57929..460bc8e93 100644
--- a/nsock/src/nsock_pool.c
+++ b/nsock/src/nsock_pool.c
@@ -181,6 +181,7 @@ nsock_pool nsock_pool_new(void *userdata) {
 
 #if HAVE_OPENSSL
   nsp->sslctx = NULL;
+  nsp->dtlsctx = NULL;
 #endif
 
   nsp->px_chain = NULL;
diff --git a/nsock/src/nsock_ssl.c b/nsock/src/nsock_ssl.c
index 7a06f519e..08ffb9716 100644
--- a/nsock/src/nsock_ssl.c
+++ b/nsock/src/nsock_ssl.c
@@ -98,8 +98,15 @@ void nsp_ssl_cleanup(struct npool *nsp)
   {
     if (nsp->sslctx != NULL)
       SSL_CTX_free(nsp->sslctx);
+#ifdef HAVE_DTLS_CLIENT_METHOD
+    if (nsp->dtlsctx != NULL)
+      SSL_CTX_free(nsp->dtlsctx);
+#endif
   }
   nsp->sslctx = NULL;
+#ifdef HAVE_DTLS_CLIENT_METHOD
+  nsp->dtlsctx = NULL;
+#endif
 }
 
 static SSL_CTX *ssl_init_helper(const SSL_METHOD *method) {
@@ -152,7 +159,7 @@ static SSL_CTX *ssl_init_common() {
  * are made from it. The connections made from this context will use only secure
  * ciphers but no server certificate verification is done. Returns the SSL_CTX
  * so you can set your own options. */
-static nsock_ssl_ctx nsock_pool_ssl_init_helper(struct npool *ms, int flags) {
+static nsock_ssl_ctx nsock_pool_ssl_init_helper(SSL_CTX *ctx, int flags) {
   char rndbuf[128];
 
   /* Get_random_bytes may or may not provide high-quality randomness. Add it to
@@ -171,17 +178,17 @@ static nsock_ssl_ctx nsock_pool_ssl_init_helper(struct npool *ms, int flags) {
   /* SSL_OP_ALL sets bug-compatibility for pretty much everything.
    * SSL_OP_NO_SSLv2 disables the less-secure SSLv2 while allowing us to use the
    * SSLv2-compatible SSLv23_client_method. */
-  SSL_CTX_set_verify(ms->sslctx, SSL_VERIFY_NONE, NULL);
-  SSL_CTX_clear_options(ms->sslctx, SSL_OP_NO_SSLv2);
-  SSL_CTX_set_options(ms->sslctx, flags & NSOCK_SSL_MAX_SPEED ?
+  SSL_CTX_set_verify(ctx, SSL_VERIFY_NONE, NULL);
+  SSL_CTX_clear_options(ctx, SSL_OP_NO_SSLv2);
+  SSL_CTX_set_options(ctx, flags & NSOCK_SSL_MAX_SPEED ?
                                   SSL_OP_ALL : SSL_OP_ALL|SSL_OP_NO_SSLv2);
 
-  if (!SSL_CTX_set_cipher_list(ms->sslctx, flags & NSOCK_SSL_MAX_SPEED ?
+  if (!SSL_CTX_set_cipher_list(ctx, flags & NSOCK_SSL_MAX_SPEED ?
                                            CIPHERS_FAST : CIPHERS_SECURE))
     fatal("Unable to set OpenSSL cipher list: %s",
           ERR_error_string(ERR_get_error(), NULL));
 
-  return ms->sslctx;
+  return ctx;
 }
 
 nsock_ssl_ctx nsock_pool_ssl_init(nsock_pool ms_pool, int flags) {
@@ -189,7 +196,7 @@ nsock_ssl_ctx nsock_pool_ssl_init(nsock_pool ms_pool, int flags) {
 
   if (ms->sslctx == NULL)
     ms->sslctx = ssl_init_common();
-  return nsock_pool_ssl_init_helper(ms, flags);
+  return nsock_pool_ssl_init_helper(ms->sslctx, flags);
 }
 
 #ifdef HAVE_DTLS_CLIENT_METHOD
@@ -205,9 +212,9 @@ nsock_ssl_ctx nsock_pool_dtls_init(nsock_pool ms_pool, int flags) {
   SSL_CTX *dtls_ctx = NULL;
   struct npool *ms = (struct npool *)ms_pool;
 
-  if (ms->sslctx == NULL)
-    ms->sslctx = dtls_init_common();
-  dtls_ctx = (SSL_CTX *) nsock_pool_ssl_init_helper(ms, flags);
+  if (ms->dtlsctx == NULL)
+    ms->dtlsctx = dtls_init_common();
+  dtls_ctx = (SSL_CTX *) nsock_pool_ssl_init_helper(ms->dtlsctx, flags);
 
   /* Don't add padding or the ClientHello will fragment and not connect properly. */
   SSL_CTX_clear_options(dtls_ctx, SSL_OP_TLSEXT_PADDING);