diff --git a/src/dtls13.c b/src/dtls13.c
index aeaaa3285..36d329e50 100644
--- a/src/dtls13.c
+++ b/src/dtls13.c
@@ -426,7 +426,7 @@ static int Dtls13SendFragFromBuffer(WOLFSSL* ssl, byte* output, word16 length)
 
 static int Dtls13SendNow(WOLFSSL* ssl, enum HandShakeType handshakeType)
 {
-    if (!ssl->options.groupMessages)
+    if (!ssl->options.groupMessages || ssl->dtls13SendingFragments)
         return 1;
 
     if (handshakeType == client_hello || handshakeType == hello_retry_request ||
diff --git a/src/tls13.c b/src/tls13.c
index dec6d88c4..1f4819c51 100644
--- a/src/tls13.c
+++ b/src/tls13.c
@@ -3339,6 +3339,7 @@ int SendTls13ClientHello(WOLFSSL* ssl)
     WOLFSSL_START(WC_FUNC_CLIENT_HELLO_SEND);
     WOLFSSL_ENTER("SendTls13ClientHello");
 
+    ssl->options.buildingMsg = 1;
     major = SSLv3_MAJOR;
     tls12minor = TLSv1_2_MINOR;
 
@@ -3613,6 +3614,7 @@ int SendTls13ClientHello(WOLFSSL* ssl)
     }
 #endif
 
+    ssl->options.buildingMsg = 0;
 #ifdef WOLFSSL_DTLS13
     if (ssl->options.dtls) {
         ret = Dtls13HandshakeSend(ssl, args->output, args->sendSz,
@@ -5615,6 +5617,7 @@ int SendTls13ServerHello(WOLFSSL* ssl, byte extMsgType)
             return ret;
     }
 
+    ssl->options.buildingMsg = 1;
 #ifdef WOLFSSL_DTLS13
     if (ssl->options.dtls)
         idx = DTLS_RECORD_HEADER_SZ + DTLS_HANDSHAKE_HEADER_SZ;
@@ -5724,6 +5727,7 @@ int SendTls13ServerHello(WOLFSSL* ssl, byte extMsgType)
     if (extMsgType == server_hello)
         ssl->options.serverState = SERVER_HELLO_COMPLETE;
 
+    ssl->options.buildingMsg = 0;
 #ifdef WOLFSSL_DTLS13
     if (ssl->options.dtls) {
         ret =  Dtls13HandshakeSend(ssl, output, sendSz, sendSz,
@@ -5765,6 +5769,7 @@ static int SendTls13EncryptedExtensions(WOLFSSL* ssl)
     WOLFSSL_START(WC_FUNC_ENCRYPTED_EXTENSIONS_SEND);
     WOLFSSL_ENTER("SendTls13EncryptedExtensions");
 
+    ssl->options.buildingMsg = 1;
     ssl->keys.encryptionOn = 1;
 
 #ifdef WOLFSSL_DTLS13
@@ -5858,6 +5863,7 @@ static int SendTls13EncryptedExtensions(WOLFSSL* ssl)
 
 #ifdef WOLFSSL_DTLS13
     if (ssl->options.dtls) {
+        ssl->options.buildingMsg = 0;
         ret = Dtls13HandshakeSend(ssl, output, sendSz, idx,
                                   encrypted_extensions, 1);
 
@@ -5878,7 +5884,7 @@ static int SendTls13EncryptedExtensions(WOLFSSL* ssl)
         return sendSz;
 
     ssl->buffers.outputBuffer.length += sendSz;
-
+    ssl->options.buildingMsg = 0;
     ssl->options.serverState = SERVER_ENCRYPTED_EXTENSIONS_COMPLETE;
 
     if (!ssl->options.groupMessages)
@@ -5915,6 +5921,8 @@ static int SendTls13CertificateRequest(WOLFSSL* ssl, byte* reqCtx,
     WOLFSSL_START(WC_FUNC_CERTIFICATE_REQUEST_SEND);
     WOLFSSL_ENTER("SendTls13CertificateRequest");
 
+    ssl->options.buildingMsg = 1;
+
     if (ssl->options.side == WOLFSSL_SERVER_END)
         InitSuitesHashSigAlgo(ssl->suites, 1, 1, 1,
                               0, 1, ssl->buffers.keySz);
@@ -5966,6 +5974,7 @@ static int SendTls13CertificateRequest(WOLFSSL* ssl, byte* reqCtx,
 
 #ifdef WOLFSSL_DTLS13
     if (ssl->options.dtls) {
+        ssl->options.buildingMsg = 0;
         ret =
             Dtls13HandshakeSend(ssl, output, sendSz, i, certificate_request, 1);
 
@@ -5993,6 +6002,7 @@ static int SendTls13CertificateRequest(WOLFSSL* ssl, byte* reqCtx,
     #endif
 
     ssl->buffers.outputBuffer.length += sendSz;
+    ssl->options.buildingMsg = 0;
     if (!ssl->options.groupMessages)
         ret = SendBuffered(ssl);
 
@@ -6498,6 +6508,8 @@ static int SendTls13Certificate(WOLFSSL* ssl)
     WOLFSSL_START(WC_FUNC_CERTIFICATE_SEND);
     WOLFSSL_ENTER("SendTls13Certificate");
 
+    ssl->options.buildingMsg = 1;
+
 #ifdef WOLFSSL_POST_HANDSHAKE_AUTH
     if (ssl->options.side == WOLFSSL_CLIENT_END && ssl->certReqCtx != NULL) {
         certReqCtxLen = ssl->certReqCtx->len;
@@ -6599,8 +6611,6 @@ static int SendTls13Certificate(WOLFSSL* ssl)
         }
 #endif /* WOLFSSL_DTLS13 */
 
-        ssl->options.buildingMsg = 1;
-
         if (ssl->fragOffset == 0) {
             if (headerSz + certSz + extSz + certChainSz <=
                                             maxFragment - HANDSHAKE_HEADER_SZ) {
@@ -6716,6 +6726,7 @@ static int SendTls13Certificate(WOLFSSL* ssl)
 #ifdef WOLFSSL_DTLS13
         if (ssl->options.dtls) {
             /* DTLS1.3 uses a separate variable and logic for fragments */
+            ssl->options.buildingMsg = 0;
             ssl->fragOffset = 0;
             ret = Dtls13HandshakeSend(ssl, output, sendSz, i, certificate, 1);
         }
@@ -6739,6 +6750,7 @@ static int SendTls13Certificate(WOLFSSL* ssl)
 #endif
 
             ssl->buffers.outputBuffer.length += sendSz;
+            ssl->options.buildingMsg = 0;
             if (!ssl->options.groupMessages)
                 ret = SendBuffered(ssl);
         }
@@ -6822,6 +6834,8 @@ static int SendTls13CertificateVerify(WOLFSSL* ssl)
     WOLFSSL_START(WC_FUNC_CERTIFICATE_VERIFY_SEND);
     WOLFSSL_ENTER("SendTls13CertificateVerify");
 
+    ssl->options.buildingMsg = 1;
+
 #if defined(WOLFSSL_RENESAS_TSIP_TLS) && (WOLFSSL_RENESAS_TSIP_VER >= 115)
     ret = tsip_Tls13SendCertVerify(ssl);
     if (ret != CRYPTOCB_UNAVAILABLE) {
@@ -7184,6 +7198,7 @@ static int SendTls13CertificateVerify(WOLFSSL* ssl)
         {
 #ifdef WOLFSSL_DTLS13
             if (ssl->options.dtls) {
+                ssl->options.buildingMsg = 0;
                 ret = Dtls13HandshakeSend(ssl, args->output,
                     MAX_CERT_VERIFY_SZ + MAX_MSG_EXTRA + MAX_MSG_EXTRA,
                     args->sendSz, certificate_verify, 1);
@@ -7219,7 +7234,7 @@ static int SendTls13CertificateVerify(WOLFSSL* ssl)
         #endif
 
             ssl->buffers.outputBuffer.length += args->sendSz;
-
+            ssl->options.buildingMsg = 0;
             if (!ssl->options.groupMessages)
                 ret = SendBuffered(ssl);
             break;
@@ -7955,6 +7970,7 @@ static int SendTls13Finished(WOLFSSL* ssl)
     WOLFSSL_START(WC_FUNC_FINISHED_SEND);
     WOLFSSL_ENTER("SendTls13Finished");
 
+    ssl->options.buildingMsg = 1;
 #ifdef WOLFSSL_DTLS13
     if (ssl->options.dtls) {
         headerSz = DTLS_HANDSHAKE_HEADER_SZ;
@@ -8057,6 +8073,7 @@ static int SendTls13Finished(WOLFSSL* ssl)
     #endif
 
     ssl->buffers.outputBuffer.length += sendSz;
+    ssl->options.buildingMsg = 0;
     }
 
     if (ssl->options.side == WOLFSSL_SERVER_END) {
@@ -8402,6 +8419,7 @@ static int SendTls13EndOfEarlyData(WOLFSSL* ssl)
 
     length = 0;
     sendSz = idx + length + MAX_MSG_EXTRA;
+    ssl->options.buildingMsg = 1;
 
     /* Check buffers are big enough and grow if needed. */
     if ((ret = CheckAvailableSize(ssl, sendSz)) != 0)
@@ -8425,6 +8443,7 @@ static int SendTls13EndOfEarlyData(WOLFSSL* ssl)
     if ((ret = SetKeysSide(ssl, ENCRYPT_SIDE_ONLY)) != 0)
         return ret;
 
+    ssl->options.buildingMsg = 0;
     if (!ssl->options.groupMessages)
         ret = SendBuffered(ssl);