Compiler/MSP430F5529: Upload not work the majority time

Tool/software: TI C/C++ Compiler

Good Afternoon, I am using the launchpad MSP430F5529 + Boosterpack CC3100 and the software Energia version 1.6.10E18 with the OS - Windows 10. I am having problem with the update. I must update multiple time for work my serial print. I would like to know the reason for the problem. I am using in a code a lot complex but when I use in a code more simple like a "Blink" I have the same problem. I already look the "device manager" of my PC like the figure that I attachment("COM12")  and already try used both selection of debugger (dslite - or mspdebug) and the problem keeps. I am use this simple blick bellow for test and I have the same problem. I would like a answer please.archive.zip

/*
Blink
The basic Energia example.
Turns on an LED on for one second, then off for one second, repeatedly.
Change the LED define to blink other LEDs.

Hardware Required:
* LaunchPad with an LED

This example code is in the public domain.
*/

// most launchpads have a red LED
#define LED RED_LED

//see pins_energia.h for more LED definitions
//#define LED GREEN_LED

// the setup routine runs once when you press reset:
void setup() {
// initialize the digital pin as an output.
Serial.begin(115200);
Serial.println("Starting Program");
pinMode(LED, OUTPUT);
}

// the loop routine runs over and over again forever:
void loop() {
digitalWrite(LED, HIGH); // turn the LED on (HIGH is the voltage level)
delay(1000); // wait for a second
Serial.println("Turn On");
digitalWrite(LED, LOW); // turn the LED off by making the voltage LOW
delay(1000); // wait for a second
Serial.println("Turn Off");
}