diff --git a/include/freerdp/freerdp.h b/include/freerdp/freerdp.h
index eb3dd33a3..a3bb73dba 100644
--- a/include/freerdp/freerdp.h
+++ b/include/freerdp/freerdp.h
@@ -482,6 +482,13 @@ extern "C"
 
 	FREERDP_API void freerdp_set_last_error(rdpContext* context, UINT32 lastError);
 
+#define freerdp_set_last_error_if_not(context, lastError)             \
+	do                                                                \
+	{                                                                 \
+		if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS) \
+			freerdp_set_last_error_log(context, lastError);           \
+	} while (0)
+
 #define freerdp_set_last_error_log(context, lastError) \
 	freerdp_set_last_error_ex((context), (lastError), __FUNCTION__, __FILE__, __LINE__)
 	FREERDP_API void freerdp_set_last_error_ex(rdpContext* context, UINT32 lastError,
diff --git a/libfreerdp/core/connection.c b/libfreerdp/core/connection.c
index 6f99c6475..ab613b3c7 100644
--- a/libfreerdp/core/connection.c
+++ b/libfreerdp/core/connection.c
@@ -365,8 +365,7 @@ BOOL rdp_client_connect(rdpRdp* rdp)
 	{
 		if (rdp_check_fds(rdp) < 0)
 		{
-			if (!freerdp_get_last_error(rdp->context))
-				freerdp_set_last_error_log(rdp->context, FREERDP_ERROR_CONNECT_TRANSPORT_FAILED);
+			freerdp_set_last_error_if_not(rdp->context, FREERDP_ERROR_CONNECT_TRANSPORT_FAILED);
 
 			return FALSE;
 		}
diff --git a/libfreerdp/core/freerdp.c b/libfreerdp/core/freerdp.c
index ef30ef20b..61ee63c0a 100644
--- a/libfreerdp/core/freerdp.c
+++ b/libfreerdp/core/freerdp.c
@@ -188,8 +188,7 @@ BOOL freerdp_connect(freerdp* instance)
 
 	if (!status || (status2 != CHANNEL_RC_OK))
 	{
-		if (!freerdp_get_last_error(rdp->context))
-			freerdp_set_last_error_log(instance->context, FREERDP_ERROR_PRE_CONNECT_FAILED);
+		freerdp_set_last_error_if_not(instance->context, FREERDP_ERROR_PRE_CONNECT_FAILED);
 
 		WLog_ERR(TAG, "freerdp_pre_connect failed");
 		goto freerdp_connect_finally;
@@ -233,8 +232,7 @@ BOOL freerdp_connect(freerdp* instance)
 	{
 		WLog_ERR(TAG, "freerdp_post_connect failed");
 
-		if (!freerdp_get_last_error(rdp->context))
-			freerdp_set_last_error_log(instance->context, FREERDP_ERROR_POST_CONNECT_FAILED);
+		freerdp_set_last_error_if_not(instance->context, FREERDP_ERROR_POST_CONNECT_FAILED);
 
 		status = FALSE;
 		goto freerdp_connect_finally;
diff --git a/libfreerdp/core/gateway/rdg.c b/libfreerdp/core/gateway/rdg.c
index 72a8b2fc3..df6058498 100644
--- a/libfreerdp/core/gateway/rdg.c
+++ b/libfreerdp/core/gateway/rdg.c
@@ -1033,13 +1033,11 @@ static BOOL rdg_tls_connect(rdpRdg* rdg, rdpTls* tls, const char* peerAddress, i
 		rdpContext* context = rdg->context;
 		if (status < 0)
 		{
-			if (!freerdp_get_last_error(context))
-				freerdp_set_last_error_log(context, FREERDP_ERROR_TLS_CONNECT_FAILED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_TLS_CONNECT_FAILED);
 		}
 		else
 		{
-			if (!freerdp_get_last_error(context))
-				freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_CANCELLED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_CANCELLED);
 		}
 
 		return FALSE;
diff --git a/libfreerdp/core/gateway/rpc.c b/libfreerdp/core/gateway/rpc.c
index f05f0e0fa..0b47024ca 100644
--- a/libfreerdp/core/gateway/rpc.c
+++ b/libfreerdp/core/gateway/rpc.c
@@ -706,13 +706,11 @@ static BOOL rpc_channel_tls_connect(RpcChannel* channel, int timeout)
 	{
 		if (tlsStatus < 0)
 		{
-			if (!freerdp_get_last_error(context))
-				freerdp_set_last_error_log(context, FREERDP_ERROR_TLS_CONNECT_FAILED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_TLS_CONNECT_FAILED);
 		}
 		else
 		{
-			if (!freerdp_get_last_error(context))
-				freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_CANCELLED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_CANCELLED);
 		}
 
 		return FALSE;
diff --git a/libfreerdp/core/gateway/rpc_client.c b/libfreerdp/core/gateway/rpc_client.c
index 1873fa2d1..23518f871 100644
--- a/libfreerdp/core/gateway/rpc_client.c
+++ b/libfreerdp/core/gateway/rpc_client.c
@@ -549,8 +549,7 @@ static int rpc_client_default_out_channel_recv(rdpRpc* rpc)
 
 			if (statusCode == HTTP_STATUS_DENIED)
 			{
-				if (!freerdp_get_last_error(rpc->context))
-					freerdp_set_last_error_log(rpc->context, FREERDP_ERROR_AUTHENTICATION_FAILED);
+				freerdp_set_last_error_if_not(rpc->context, FREERDP_ERROR_AUTHENTICATION_FAILED);
 			}
 
 			http_response_free(response);
diff --git a/libfreerdp/core/mcs.c b/libfreerdp/core/mcs.c
index 6c835c70a..975dc9c13 100644
--- a/libfreerdp/core/mcs.c
+++ b/libfreerdp/core/mcs.c
@@ -1236,8 +1236,7 @@ BOOL mcs_client_begin(rdpMcs* mcs)
 
 	if (!mcs_send_connect_initial(mcs))
 	{
-		if (!freerdp_get_last_error(context))
-			freerdp_set_last_error_log(context, FREERDP_ERROR_MCS_CONNECT_INITIAL_ERROR);
+		freerdp_set_last_error_if_not(context, FREERDP_ERROR_MCS_CONNECT_INITIAL_ERROR);
 
 		WLog_ERR(TAG, "Error: unable to send MCS Connect Initial");
 		return FALSE;
diff --git a/libfreerdp/core/tcp.c b/libfreerdp/core/tcp.c
index c31959507..4b72eac87 100644
--- a/libfreerdp/core/tcp.c
+++ b/libfreerdp/core/tcp.c
@@ -793,8 +793,7 @@ static BOOL freerdp_tcp_is_hostname_resolvable(rdpContext* context, const char*
 
 	if (!result)
 	{
-		if (!freerdp_get_last_error(context))
-			freerdp_set_last_error_log(context, FREERDP_ERROR_DNS_NAME_NOT_FOUND);
+		freerdp_set_last_error_if_not(context, FREERDP_ERROR_DNS_NAME_NOT_FOUND);
 
 		return FALSE;
 	}
@@ -1074,8 +1073,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 
 	if (!hostname)
 	{
-		if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-			freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_FAILED);
+		freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_FAILED);
 
 		return -1;
 	}
@@ -1092,8 +1090,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 
 		if (sockfd < 0)
 		{
-			if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-				freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_FAILED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_FAILED);
 
 			return -1;
 		}
@@ -1128,8 +1125,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 
 			if (!result)
 			{
-				if (!freerdp_get_last_error(context))
-					freerdp_set_last_error_log(context, FREERDP_ERROR_DNS_NAME_NOT_FOUND);
+				freerdp_set_last_error_if_not(context, FREERDP_ERROR_DNS_NAME_NOT_FOUND);
 
 				return -1;
 			}
@@ -1154,8 +1150,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 
 			if (sockfd < 0)
 			{
-				if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-					freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_FAILED);
+				freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_FAILED);
 
 				freeaddrinfo(result);
 				return -1;
@@ -1174,8 +1169,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 				freeaddrinfo(result);
 				close(sockfd);
 
-				if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-					freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_FAILED);
+				freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_FAILED);
 
 				WLog_ERR(TAG, "failed to connect to %s", hostname);
 				return -1;
@@ -1193,8 +1187,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 		if (!useExternalDefinedSocket)
 			close(sockfd);
 
-		if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-			freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_FAILED);
+		freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_FAILED);
 
 		WLog_ERR(TAG, "Couldn't get socket ip address");
 		return -1;
@@ -1221,8 +1214,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 			{
 				close(sockfd);
 
-				if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-					freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_FAILED);
+				freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_FAILED);
 
 				WLog_ERR(TAG, "unable to set receive buffer len");
 				return -1;
@@ -1236,8 +1228,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 		{
 			close(sockfd);
 
-			if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-				freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_FAILED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_FAILED);
 
 			WLog_ERR(TAG, "Couldn't set keep alive mode.");
 			return -1;
@@ -1248,8 +1239,7 @@ int freerdp_tcp_connect(rdpContext* context, rdpSettings* settings, const char*
 	{
 		close(sockfd);
 
-		if (freerdp_get_last_error(context) == FREERDP_ERROR_SUCCESS)
-			freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_CANCELLED);
+		freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_CANCELLED);
 
 		return -1;
 	}
diff --git a/libfreerdp/core/transport.c b/libfreerdp/core/transport.c
index db3a887e8..a24052ffe 100644
--- a/libfreerdp/core/transport.c
+++ b/libfreerdp/core/transport.c
@@ -190,8 +190,7 @@ static void transport_ssl_cb(SSL* ssl, int where, int ret)
 #endif /* WITH_GSSAPI */
 						kret = FREERDP_ERROR_CONNECT_PASSWORD_CERTAINLY_EXPIRED;
 
-					if (!freerdp_get_last_error(transport->context))
-						freerdp_set_last_error_log(transport->context, kret);
+					freerdp_set_last_error_if_not(transport->context, kret);
 				}
 
 				break;
@@ -290,13 +289,11 @@ BOOL transport_connect_tls(rdpTransport* transport)
 	{
 		if (tlsStatus < 0)
 		{
-			if (!freerdp_get_last_error(context))
-				freerdp_set_last_error_log(context, FREERDP_ERROR_TLS_CONNECT_FAILED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_TLS_CONNECT_FAILED);
 		}
 		else
 		{
-			if (!freerdp_get_last_error(context))
-				freerdp_set_last_error_log(context, FREERDP_ERROR_CONNECT_CANCELLED);
+			freerdp_set_last_error_if_not(context, FREERDP_ERROR_CONNECT_CANCELLED);
 		}
 
 		return FALSE;
@@ -346,8 +343,7 @@ BOOL transport_connect_nla(rdpTransport* transport)
 	{
 		WLog_Print(transport->log, WLOG_ERROR, "NLA begin failed");
 
-		if (!freerdp_get_last_error(context))
-			freerdp_set_last_error_log(context, FREERDP_ERROR_AUTHENTICATION_FAILED);
+		freerdp_set_last_error_if_not(context, FREERDP_ERROR_AUTHENTICATION_FAILED);
 
 		transport_set_nla_mode(transport, FALSE);
 		return FALSE;
@@ -1009,8 +1005,7 @@ int transport_check_fds(rdpTransport* transport)
 	if (transport->layer == TRANSPORT_LAYER_CLOSED)
 	{
 		WLog_Print(transport->log, WLOG_DEBUG, "transport_check_fds: transport layer closed");
-		if (freerdp_get_last_error(transport->context) == FREERDP_ERROR_SUCCESS)
-			freerdp_set_last_error_log(transport->context, FREERDP_ERROR_CONNECT_TRANSPORT_FAILED);
+		freerdp_set_last_error_if_not(transport->context, FREERDP_ERROR_CONNECT_TRANSPORT_FAILED);
 		return -1;
 	}