diff --git a/include/polarssl/ssl.h b/include/polarssl/ssl.h
index 2c2bedab07..bd7f1f775b 100644
--- a/include/polarssl/ssl.h
+++ b/include/polarssl/ssl.h
@@ -1682,6 +1682,13 @@ int ssl_close_notify( ssl_context *ssl );
  */
 void ssl_free( ssl_context *ssl );
 
+/**
+ * \brief          Initialize SSL session structure
+ *
+ * \param session  SSL session
+ */
+void ssl_session_init( ssl_session *session );
+
 /**
  * \brief          Free referenced items in an SSL session including the
  *                 peer certificate and clear memory
diff --git a/library/ssl_srv.c b/library/ssl_srv.c
index 1e75408eeb..9d2507a3b6 100644
--- a/library/ssl_srv.c
+++ b/library/ssl_srv.c
@@ -343,6 +343,8 @@ static int ssl_parse_ticket( ssl_context *ssl,
 
     ssl_session_free( ssl->session_negotiate );
     memcpy( ssl->session_negotiate, &session, sizeof( ssl_session ) );
+
+    /* Zeroize instead of free as we copied the content */
     polarssl_zeroize( &session, sizeof( ssl_session ) );
 
     return( 0 );
diff --git a/library/ssl_tls.c b/library/ssl_tls.c
index a6761adce4..d3bfab5188 100644
--- a/library/ssl_tls.c
+++ b/library/ssl_tls.c
@@ -3270,80 +3270,108 @@ int ssl_parse_finished( ssl_context *ssl )
     return( 0 );
 }
 
+static void ssl_handshake_params_init( ssl_handshake_params *handshake,
+                                       ssl_key_cert *key_cert )
+{
+    memset( handshake, 0, sizeof( ssl_handshake_params ) );
+
+#if defined(POLARSSL_SSL_PROTO_SSL3) || defined(POLARSSL_SSL_PROTO_TLS1) || \
+    defined(POLARSSL_SSL_PROTO_TLS1_1)
+     md5_init(   &handshake->fin_md5  );
+    sha1_init(   &handshake->fin_sha1 );
+     md5_starts( &handshake->fin_md5  );
+    sha1_starts( &handshake->fin_sha1 );
+#endif
+#if defined(POLARSSL_SSL_PROTO_TLS1_2)
+#if defined(POLARSSL_SHA256_C)
+    sha256_init(   &handshake->fin_sha256    );
+    sha256_starts( &handshake->fin_sha256, 0 );
+#endif
+#if defined(POLARSSL_SHA512_C)
+    sha512_init(   &handshake->fin_sha512    );
+    sha512_starts( &handshake->fin_sha512, 1 );
+#endif
+#endif /* POLARSSL_SSL_PROTO_TLS1_2 */
+
+    handshake->update_checksum = ssl_update_checksum_start;
+    handshake->sig_alg = SSL_HASH_SHA1;
+
+#if defined(POLARSSL_DHM_C)
+    dhm_init( &handshake->dhm_ctx );
+#endif
+#if defined(POLARSSL_ECDH_C)
+    ecdh_init( &handshake->ecdh_ctx );
+#endif
+
+#if defined(POLARSSL_X509_CRT_PARSE_C)
+    handshake->key_cert = key_cert;
+#endif
+}
+
+static void ssl_transform_init( ssl_transform *transform )
+{
+    memset( transform, 0, sizeof(ssl_transform) );
+}
+
+void ssl_session_init( ssl_session *session )
+{
+    memset( session, 0, sizeof(ssl_session) );
+}
+
 static int ssl_handshake_init( ssl_context *ssl )
 {
+    /* Clear old handshake information if present */
     if( ssl->transform_negotiate )
         ssl_transform_free( ssl->transform_negotiate );
-    else
+    if( ssl->session_negotiate )
+        ssl_session_free( ssl->session_negotiate );
+    if( ssl->handshake )
+        ssl_handshake_free( ssl->handshake );
+
+    /*
+     * Either the pointers are now NULL or cleared properly and can be freed.
+     * Now allocate missing structures.
+     */
+    if( ssl->transform_negotiate == NULL )
     {
         ssl->transform_negotiate =
             (ssl_transform *) polarssl_malloc( sizeof(ssl_transform) );
-
-        if( ssl->transform_negotiate != NULL )
-            memset( ssl->transform_negotiate, 0, sizeof(ssl_transform) );
     }
 
-    if( ssl->session_negotiate )
-        ssl_session_free( ssl->session_negotiate );
-    else
+    if( ssl->session_negotiate == NULL )
     {
         ssl->session_negotiate =
             (ssl_session *) polarssl_malloc( sizeof(ssl_session) );
-
-        if( ssl->session_negotiate != NULL )
-            memset( ssl->session_negotiate, 0, sizeof(ssl_session) );
     }
 
-    if( ssl->handshake )
-        ssl_handshake_free( ssl->handshake );
-    else
+    if( ssl->handshake == NULL)
     {
         ssl->handshake = (ssl_handshake_params *)
             polarssl_malloc( sizeof(ssl_handshake_params) );
-
-        if( ssl->handshake != NULL )
-            memset( ssl->handshake, 0, sizeof(ssl_handshake_params) );
     }
 
+    /* All pointers should exist and can be directly freed without issue */
     if( ssl->handshake == NULL ||
         ssl->transform_negotiate == NULL ||
         ssl->session_negotiate == NULL )
     {
         SSL_DEBUG_MSG( 1, ( "malloc() of ssl sub-contexts failed" ) );
+
+        polarssl_free( ssl->handshake );
+        polarssl_free( ssl->transform_negotiate );
+        polarssl_free( ssl->session_negotiate );
+
+        ssl->handshake = NULL;
+        ssl->transform_negotiate = NULL;
+        ssl->session_negotiate = NULL;
+
         return( POLARSSL_ERR_SSL_MALLOC_FAILED );
     }
 
-#if defined(POLARSSL_SSL_PROTO_SSL3) || defined(POLARSSL_SSL_PROTO_TLS1) || \
-    defined(POLARSSL_SSL_PROTO_TLS1_1)
-     md5_init(   &ssl->handshake->fin_md5  );
-    sha1_init(   &ssl->handshake->fin_sha1 );
-     md5_starts( &ssl->handshake->fin_md5  );
-    sha1_starts( &ssl->handshake->fin_sha1 );
-#endif
-#if defined(POLARSSL_SSL_PROTO_TLS1_2)
-#if defined(POLARSSL_SHA256_C)
-    sha256_init(   &ssl->handshake->fin_sha256    );
-    sha256_starts( &ssl->handshake->fin_sha256, 0 );
-#endif
-#if defined(POLARSSL_SHA512_C)
-    sha512_init(   &ssl->handshake->fin_sha512    );
-    sha512_starts( &ssl->handshake->fin_sha512, 1 );
-#endif
-#endif /* POLARSSL_SSL_PROTO_TLS1_2 */
-
-    ssl->handshake->update_checksum = ssl_update_checksum_start;
-    ssl->handshake->sig_alg = SSL_HASH_SHA1;
-
-#if defined(POLARSSL_DHM_C)
-    dhm_init( &ssl->handshake->dhm_ctx );
-#endif
-#if defined(POLARSSL_ECDH_C)
-    ecdh_init( &ssl->handshake->ecdh_ctx );
-#endif
-
-#if defined(POLARSSL_X509_CRT_PARSE_C)
-    ssl->handshake->key_cert = ssl->key_cert;
-#endif
+    /* Initialize structures */
+    ssl_session_init( ssl->session_negotiate );
+    ssl_transform_init( ssl->transform_negotiate );
+    ssl_handshake_params_init( ssl->handshake, ssl->key_cert );
 
     return( 0 );
 }
@@ -4470,6 +4498,9 @@ int ssl_close_notify( ssl_context *ssl )
 
 void ssl_transform_free( ssl_transform *transform )
 {
+    if( transform == NULL )
+        return;
+
 #if defined(POLARSSL_ZLIB_SUPPORT)
     deflateEnd( &transform->ctx_deflate );
     inflateEnd( &transform->ctx_inflate );
@@ -4507,6 +4538,9 @@ static void ssl_key_cert_free( ssl_key_cert *key_cert )
 
 void ssl_handshake_free( ssl_handshake_params *handshake )
 {
+    if( handshake == NULL )
+        return;
+
 #if defined(POLARSSL_DHM_C)
     dhm_free( &handshake->dhm_ctx );
 #endif
@@ -4543,6 +4577,9 @@ void ssl_handshake_free( ssl_handshake_params *handshake )
 
 void ssl_session_free( ssl_session *session )
 {
+    if( session == NULL )
+        return;
+
 #if defined(POLARSSL_X509_CRT_PARSE_C)
     if( session->peer_cert != NULL )
     {
@@ -4563,6 +4600,9 @@ void ssl_session_free( ssl_session *session )
  */
 void ssl_free( ssl_context *ssl )
 {
+    if( ssl == NULL )
+        return;
+
     SSL_DEBUG_MSG( 2, ( "=> free" ) );
 
     if( ssl->out_ctr != NULL )