ESP32 WakeUp Deep Sleep GPIO2 and SMTP

I am trying to create a ESP32 SMTP eMail when GPIO2 is pushed. Using these two examples: SMTP: Link and Deep Sleep: Link

I have two Issues, first on ESP32 boot an SMTP eMail I only want SMTP on GPIO2 is pushed. Second I get an error on GPIO2 after second push. Error: Error, Status Code: 554, Error Code: -109, Reason: send body failed

#include <Arduino.h>
#if defined(ESP32)
  #include <WiFi.h>
#elif defined(ESP8266)
  #include <ESP8266WiFi.h>
#endif
#include <ESP_Mail_Client.h>

#define WIFI_SSID "REPLACE_WITH_YOUR_SSID"
#define WIFI_PASSWORD "REPLACE_WITH_YOUR_PASSWORD"

/** The smtp host name e.g. smtp.gmail.com for GMail or smtp.office365.com for Outlook or smtp.mail.yahoo.com */
#define SMTP_HOST "smtp.mail.com"
#define SMTP_PORT 587

/* The sign in credentials */
#define AUTHOR_EMAIL "YOUR_EMAIL@XXXX.com"
#define AUTHOR_PASSWORD "YOUR_EMAIL_APP_PASS"

/* Recipient's email*/
#define RECIPIENT_EMAIL "RECIPIENTE_EMAIL@XXXX.com"

/* Declare the global used SMTPSession object for SMTP transport */
SMTPSession smtp;

/* Callback function to get the Email sending status */
void smtpCallback(SMTP_Status status);


RTC_DATA_ATTR int bootCount = 0;

/*
Method to print the reason by which ESP32
has been awaken from sleep
*/
void print_wakeup_reason(){
  esp_sleep_wakeup_cause_t wakeup_reason;

  wakeup_reason = esp_sleep_get_wakeup_cause();

  switch(wakeup_reason)
  {
    case ESP_SLEEP_WAKEUP_EXT0 : Serial.println("Wakeup caused by external signal using RTC_IO"); break;
    case ESP_SLEEP_WAKEUP_EXT1 : Serial.println("Wakeup caused by external signal using RTC_CNTL"); break;
    case ESP_SLEEP_WAKEUP_TIMER : Serial.println("Wakeup caused by timer"); break;
    case ESP_SLEEP_WAKEUP_TOUCHPAD : Serial.println("Wakeup caused by touchpad"); break;
    case ESP_SLEEP_WAKEUP_ULP : Serial.println("Wakeup caused by ULP program"); break;
    default : Serial.printf("Wakeup was not caused by deep sleep: %d\n",wakeup_reason); break;
  }
}

void setup(){
  Serial.begin(115200);
  Serial.println();
  WiFi.begin(WIFI_SSID, WIFI_PASSWORD);
  Serial.print("Connecting to Wi-Fi");
  while (WiFi.status() != WL_CONNECTED){
    Serial.print(".");
  delay(1000); //Take some time to open up the Serial Monitor

  //Increment boot number and print it every reboot
  ++bootCount;
  Serial.println("Boot number: " + String(bootCount));

  //Print the wakeup reason for ESP32
  print_wakeup_reason();

  }
  Serial.println();
  Serial.print("Connected with IP: ");
  Serial.println(WiFi.localIP());
  Serial.println();

  /*  Set the network reconnection option */
  MailClient.networkReconnect(true);

  /** Enable the debug via Serial port
   * 0 for no debugging
   * 1 for basic level debugging
   *
   * Debug port can be changed via ESP_MAIL_DEFAULT_DEBUG_PORT in ESP_Mail_FS.h
   */
  smtp.debug(1);

  /* Set the callback function to get the sending results */
  smtp.callback(smtpCallback);

  /* Declare the Session_Config for user defined session credentials */
  Session_Config config;

  /* Set the session config */
  config.server.host_name = SMTP_HOST;
  config.server.port = SMTP_PORT;
  config.login.email = AUTHOR_EMAIL;
  config.login.password = AUTHOR_PASSWORD;
  config.login.user_domain = "";

  /*
  Set the NTP config time
  For times east of the Prime Meridian use 0-12
  For times west of the Prime Meridian add 12 to the offset.
  Ex. American/Denver GMT would be -6. 6 + 12 = 18
  See https://en.wikipedia.org/wiki/Time_zone for a list of the GMT/UTC timezone offsets
  */
  config.time.ntp_server = F("pool.ntp.org,time.nist.gov");
  config.time.gmt_offset = -6;
  config.time.day_light_offset = 0;

  /* Declare the message class */
  SMTP_Message message;

  /* Set the message headers */
  message.sender.name = F("ESP");
  message.sender.email = AUTHOR_EMAIL;
  message.subject = F("ESP Test Email");
  message.addRecipient(F("SMTP"), RECIPIENT_EMAIL);
    
  /*Send HTML message*/
  /*String htmlMsg = "<div style=\"color:#2f4468;\"><h1>Hello World!</h1><p>- Sent from ESP board</p></div>";
  message.html.content = htmlMsg.c_str();
  message.html.content = htmlMsg.c_str();
  message.text.charSet = "us-ascii";
  message.html.transfer_encoding = Content_Transfer_Encoding::enc_7bit;*/

   
  //Send raw text message
  String textMsg = "Hello World! - Sent from ESP board";
  message.text.content = textMsg.c_str();
  message.text.charSet = "us-ascii";
  message.text.transfer_encoding = Content_Transfer_Encoding::enc_7bit;
  
  message.priority = esp_mail_smtp_priority::esp_mail_smtp_priority_low;
  message.response.notify = esp_mail_smtp_notify_success | esp_mail_smtp_notify_failure | esp_mail_smtp_notify_delay;


  /* Connect to the server */
  if (!smtp.connect(&config)){
    ESP_MAIL_PRINTF("Connection error, Status Code: %d, Error Code: %d, Reason: %s", smtp.statusCode(), smtp.errorCode(), smtp.errorReason().c_str());
    return;
  }

  if (!smtp.isLoggedIn()){
    Serial.println("\nNot yet logged in.");
  }
  else{
    if (smtp.isAuthenticated())
      Serial.println("\nSuccessfully logged in.");
    else
      Serial.println("\nConnected with no Auth.");
  }

  /* Start sending Email and close the session */
  if (!MailClient.sendMail(&smtp, &message))
    ESP_MAIL_PRINTF("Error, Status Code: %d, Error Code: %d, Reason: %s", smtp.statusCode(), smtp.errorCode(), smtp.errorReason().c_str());
  /*
  First we configure the wake up source
  We set our ESP32 to wake up for an external trigger.
  There are two types for ESP32, ext0 and ext1 .
  ext0 uses RTC_IO to wakeup thus requires RTC peripherals
  to be on while ext1 uses RTC Controller so doesnt need
  peripherals to be powered on.
  Note that using internal pullups/pulldowns also requires
  RTC peripherals to be turned on.
  */
  esp_sleep_enable_ext0_wakeup(GPIO_NUM_2,1); //1 = High, 0 = Low

  //If you were to use ext1, you would use it like
  //esp_sleep_enable_ext1_wakeup(BUTTON_PIN_BITMASK,ESP_EXT1_WAKEUP_ANY_HIGH);

  //Go to sleep now
  Serial.println("Going to sleep now");
  delay(1000);

  esp_deep_sleep_start();
  Serial.println("This will never be printed");
}

void loop(){
}

/* Callback function to get the Email sending status */
void smtpCallback(SMTP_Status status){
  /* Print the current status */
  Serial.println(status.info());

  /* Print the sending result */
  if (status.success()){
    // ESP_MAIL_PRINTF used in the examples is for format printing via debug Serial port
    // that works for all supported Arduino platform SDKs e.g. AVR, SAMD, ESP32 and ESP8266.
    // In ESP8266 and ESP32, you can use Serial.printf directly.

    Serial.println("----------------");
    ESP_MAIL_PRINTF("Message sent success: %d\n", status.completedCount());
    ESP_MAIL_PRINTF("Message sent failed: %d\n", status.failedCount());
    Serial.println("----------------\n");

    for (size_t i = 0; i < smtp.sendingResult.size(); i++)
    {
      /* Get the result item */
      SMTP_Result result = smtp.sendingResult.getItem(i);

      // In case, ESP32, ESP8266 and SAMD device, the timestamp get from result.timestamp should be valid if
      // your device time was synched with NTP server.
      // Other devices may show invalid timestamp as the device time was not set i.e. it will show Jan 1, 1970.
      // You can call smtp.setSystemTime(xxx) to set device time manually. Where xxx is timestamp (seconds since Jan 1, 1970)
      
      ESP_MAIL_PRINTF("Message No: %d\n", i + 1);
      ESP_MAIL_PRINTF("Status: %s\n", result.completed ? "success" : "failed");
      ESP_MAIL_PRINTF("Date/Time: %s\n", MailClient.Time.getDateTimeString(result.timestamp, "%B %d, %Y %H:%M:%S").c_str());
      ESP_MAIL_PRINTF("Recipient: %s\n", result.recipients.c_str());
      ESP_MAIL_PRINTF("Subject: %s\n", result.subject.c_str());
    }
    Serial.println("----------------\n");

    // You need to clear sending result as the memory usage will grow up.
    smtp.sendingResult.clear();
  }
}

Looks like commenting out time server seems to fix the second GPIO2 push button issue. Error: Error, Status Code: 554, Error Code: -109, Reason: send body failed. I do get a SMTP 406 Error, but email is still sent. also the below code fixed SMTP Send eMail on Boot.

#include <Arduino.h>
#if defined(ESP32)
  #include <WiFi.h>
#elif defined(ESP8266)
  #include <ESP8266WiFi.h>
#endif
#include <ESP_Mail_Client.h>

#define WIFI_SSID  "REPLACE_WITH_YOUR_SSID"
#define WIFI_PASSWORD "REPLACE_WITH_YOUR_PASSWORD"

#define SMTP_HOST "smtp.mail.com"
#define SMTP_PORT 587

/* The sign in credentials */
#define AUTHOR_EMAIL “YOUR_EMAIL@XXXX.com”
#define AUTHOR_PASSWORD "YOUR_EMAIL_APP_PASS"

/* Recipient's email*/
#define RECIPIENT_EMAIL “RECIPIENTE_EMAIL@XXXX.com”


SMTPSession smtp;

void smtpCallback(SMTP_Status status);

RTC_DATA_ATTR int bootCount = 0;

void print_wakeup_reason() {
  esp_sleep_wakeup_cause_t wakeup_reason;
  wakeup_reason = esp_sleep_get_wakeup_cause();
  switch(wakeup_reason) {
    case ESP_SLEEP_WAKEUP_EXT0 : Serial.println("Wakeup caused by external signal using RTC_IO"); break;
    default : Serial.printf("Wakeup was not caused by deep sleep: %d\n",wakeup_reason); break;
  }
}

void sendEmail() {
  Serial.println("Sending Email...");
  smtp.debug(1);
  smtp.callback(smtpCallback);

  Session_Config config;
  config.server.host_name = SMTP_HOST;
  config.server.port = SMTP_PORT;
  config.login.email = AUTHOR_EMAIL;
  config.login.password = AUTHOR_PASSWORD;
  config.login.user_domain = "";
  //config.time.ntp_server = F("pool.ntp.org,time.nist.gov");
  //config.time.gmt_offset = -6;
  //config.time.day_light_offset = 0;

  SMTP_Message message;
  message.sender.name = F("ESP");
  message.sender.email = AUTHOR_EMAIL;
  message.subject = F("ESP Test Email");
  message.addRecipient(F("SMTP"), RECIPIENT_EMAIL);

  String textMsg = "Hello World! - Sent from ESP board";
  message.text.content = textMsg.c_str();
  message.text.charSet = "us-ascii";
  message.text.transfer_encoding = Content_Transfer_Encoding::enc_7bit;
  message.priority = esp_mail_smtp_priority::esp_mail_smtp_priority_low;
  message.response.notify = esp_mail_smtp_notify_success | esp_mail_smtp_notify_failure | esp_mail_smtp_notify_delay;

  if (!smtp.connect(&config)) {
    Serial.println("Connection error");
    return;
  }

  if (!MailClient.sendMail(&smtp, &message)) {
    Serial.println("Error sending email");
  }
}

void setup() {
  Serial.begin(115200);
  Serial.println();
  WiFi.begin(WIFI_SSID, WIFI_PASSWORD);
  Serial.print("Connecting to Wi-Fi");

  while (WiFi.status() != WL_CONNECTED) {
    Serial.print(".");
    delay(1000);
  }

  Serial.println("\nConnected to Wi-Fi.");

  print_wakeup_reason();

  // Check if GPIO2 is HIGH (button pressed) before sending email
  if (digitalRead(2) == HIGH) {
    sendEmail();
  }

  // Enable external wake-up on GPIO2, high level trigger
  esp_sleep_enable_ext0_wakeup(GPIO_NUM_2, 1);

  Serial.println("Going to sleep now");
  esp_deep_sleep_start();
}

void loop() {
  // Not used due to deep sleep
}

void smtpCallback(SMTP_Status status) {
  Serial.println(status.info());

  if (status.success()) {
    Serial.println("Email sent successfully");
  } else {
    Serial.print("Error Code: ");
    Serial.println(smtp.errorCode());
  }
}

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