diff --git a/src/internal.c b/src/internal.c
index edab14eb4..db70d0f6f 100644
--- a/src/internal.c
+++ b/src/internal.c
@@ -1096,7 +1096,7 @@ WOLFSSH* SshInit(WOLFSSH* ssh, WOLFSSH_CTX* ctx)
     ssh->fs            = NULL;
     ssh->acceptState = ACCEPT_BEGIN;
     ssh->clientState = CLIENT_BEGIN;
-    ssh->isKeying    = 1;
+    ssh->isKeying    = 0; /* initial state of not keying yet */
     ssh->authId      = ID_USERAUTH_PUBLICKEY;
     ssh->supportedAuth[0] = ID_USERAUTH_PUBLICKEY;
     ssh->supportedAuth[1] = ID_USERAUTH_PASSWORD;
@@ -4058,6 +4058,15 @@ static int DoKexInit(WOLFSSH* ssh, byte* buf, word32 len, word32* idx)
         ret = WS_BAD_ARGUMENT;
     }
 
+    if (ret == WS_SUCCESS) {
+        /* Check if already in process of keying and error out if so. */
+        if (ssh->isKeying & WOLFSSH_PEER_IS_KEYING) {
+            WLOG(WS_LOG_ERROR,
+                "Already in keying process and got KEX init");
+            ret = WS_INVALID_STATE_E;
+        }
+    }
+
     /*
      * I don't need to save what the client sends here. I should decode
      * each list into a local array of IDs, and pick the one the peer is
@@ -4067,6 +4076,8 @@ static int DoKexInit(WOLFSSH* ssh, byte* buf, word32 len, word32* idx)
      */
 
     if (ret == WS_SUCCESS) {
+        /* Set peer is keying flag after receiving SSH_MSG_KEX_INIT */
+        ssh->isKeying |= WOLFSSH_PEER_IS_KEYING;
         if (ssh->handshake == NULL) {
             ssh->handshake = HandshakeInfoNew(ssh->ctx->heap);
             if (ssh->handshake == NULL) {
@@ -4327,7 +4338,8 @@ static int DoKexInit(WOLFSSH* ssh, byte* buf, word32 len, word32* idx)
         byte scratchLen[LENGTH_SZ];
         word32 strSz = 0;
 
-        if (!ssh->isKeying) {
+        /* respond with KEX Init message if not having initiated the keying */
+        if ((ssh->isKeying & WOLFSSH_SELF_IS_KEYING) == 0) {
             WLOG(WS_LOG_DEBUG, "Keying initiated");
             ret = SendKexInit(ssh);
         }
@@ -5881,6 +5893,13 @@ static int DoNewKeys(WOLFSSH* ssh, byte* buf, word32 len, word32* idx)
     if (ssh == NULL || ssh->handshake == NULL)
         ret = WS_BAD_ARGUMENT;
 
+    if (ret == WS_SUCCESS) {
+        if (ssh->isKeying & WOLFSSH_SELF_IS_KEYING) {
+            WLOG(WS_LOG_ERROR, "Keying failed");
+            ret = WS_INVALID_STATE_E;
+        }
+    }
+
     if (ret == WS_SUCCESS) {
         ssh->peerEncryptId = ssh->handshake->encryptId;
         ssh->peerMacId = ssh->handshake->macId;
@@ -5941,7 +5960,9 @@ static int DoNewKeys(WOLFSSH* ssh, byte* buf, word32 len, word32* idx)
     if (ret == WS_SUCCESS) {
         ssh->rxCount = 0;
         ssh->highwaterFlag = 0;
-        ssh->isKeying = 0;
+
+        /* Clear peer is keying flag */
+        ssh->isKeying &= ~WOLFSSH_PEER_IS_KEYING;
         HandshakeInfoFree(ssh->handshake, ssh->ctx->heap);
         ssh->handshake = NULL;
         WLOG(WS_LOG_DEBUG, "Keying completed");
@@ -9405,7 +9426,7 @@ static int DoPacket(WOLFSSH* ssh, byte* bufferConsumed)
         case MSGID_KEXINIT:
             WLOG(WS_LOG_DEBUG, "Decoding MSGID_KEXINIT");
             ret = DoKexInit(ssh, buf + idx, payloadSz, &payloadIdx);
-            if (ssh->isKeying == 1 &&
+            if (ssh->isKeying &&
                     ssh->connectState == CONNECT_SERVER_CHANNEL_REQUEST_DONE) {
                 if (ssh->handshake->kexId == ID_DH_GEX_SHA256) {
 #if !defined(WOLFSSH_NO_DH) && !defined(WOLFSSH_NO_DH_GEX_SHA256)
@@ -10501,7 +10522,8 @@ int SendKexInit(WOLFSSH* ssh)
     }
 
     if (ret == WS_SUCCESS) {
-        ssh->isKeying = 1;
+        /* Set self is keying flag since we started sending the KEX init msg */
+        ssh->isKeying |= WOLFSSH_SELF_IS_KEYING;
         if (ssh->handshake == NULL) {
             ssh->handshake = HandshakeInfoNew(ssh->ctx->heap);
             if (ssh->handshake == NULL) {
@@ -12534,9 +12556,13 @@ int SendNewKeys(WOLFSSH* ssh)
         ssh->txCount = 0;
     }
 
-    if (ret == WS_SUCCESS)
+    if (ret == WS_SUCCESS) {
         ret = wolfSSH_SendPacket(ssh);
 
+        /* Clear self is keying flag */
+        ssh->isKeying &= ~WOLFSSH_SELF_IS_KEYING;
+    }
+
     WLOG(WS_LOG_DEBUG, "Leaving SendNewKeys(), ret = %d", ret);
     return ret;
 }
diff --git a/wolfssh/internal.h b/wolfssh/internal.h
index 1b7dada16..6df5f1147 100644
--- a/wolfssh/internal.h
+++ b/wolfssh/internal.h
@@ -473,6 +473,11 @@ enum NameIdType {
     #define WOLFSSH_KEY_QUANTITY_REQ 1
 #endif
 
+/* Keep track of keying state for both sides of the connection.
+ * WOLFSSH_SELF_IS_KEYING gets set on sending KEX init and
+ * WOLFSSH_PEER_IS_KEYING gets set on receiving KEX init */
+#define WOLFSSH_PEER_IS_KEYING 0x01
+#define WOLFSSH_SELF_IS_KEYING 0x02
 
 WOLFSSH_LOCAL byte NameToId(const char* name, word32 nameSz);
 WOLFSSH_LOCAL const char* IdToName(byte id);