Azure Event Grid esp-mqtt-arduino Client – Success

Still couldn’t figure out why my code was failing so I turned up logging to 11 and noticed a couple of messages which didn’t make sense. The device was connecting than disconnecting which indicated a another problem. As part of the Message Queue Telemetry Transport(MQTT) specification there is a “feature” Last Will and Testament(LWT) which a client can configure so that the MQTT broker sends a message to a topic if the device disconnects unexpectedly.

I was looking at the code and noticed that LWT was being used and that the topic didn’t exist in my Azure Event Grid MQTT Broker namespace. When the LWT configuration was commented out the application worked.

void Mqtt5ClientESP32::begin(const char* uri, const char* client_id, const char* user, const char* pass, bool use_v5) {
  connected_ = false;
  insecure_ = false;
  cfg_.broker.address.uri = uri;
  if (client_id) cfg_.credentials.client_id = client_id;
  if (user)      cfg_.credentials.username  = user;
  if (pass)      cfg_.credentials.authentication.password = pass;

  cfg_.broker.verification.use_global_ca_store = false;
  cfg_.broker.verification.certificate = nullptr;
  cfg_.broker.verification.certificate_len = 0;
  cfg_.broker.verification.skip_cert_common_name_check = false;
  
/*
  cfg_.session.last_will.topic  = "devices/esp32/lwt";
  cfg_.session.last_will.msg    = "offline";
  cfg_.session.last_will.qos    = 1;
  cfg_.session.last_will.retain = true;
*/

cfg_.session.protocol_ver = 
#if CONFIG_MQTT_PROTOCOL_5
      use_v5 ? MQTT_PROTOCOL_V_5 : MQTT_PROTOCOL_V_3_1_1;
#else
      MQTT_PROTOCOL_V_3_1_1;
  (void)use_v5;  // MQTT v5 support disabled at build time
#endif
}

Two methods were added so that the LWT could be configured if required

void SetLWT(const char *topic, const char *msg, int msg_len,int qos, int retain);
void Mqtt5ClientESP32::SetLWT(const char *topic, const char *msg, int msg_len,int qos, int retain){
   cfg_.session.last_will.topic  = topic;
   cfg_.session.last_will.msg    = msg;
   cfg_.session.last_will.msg_len= msg_len;
   cfg_.session.last_will.qos    = qos;
   cfg_.session.last_will.retain = retain;
}

Paying close attention to the logging I noticed the “Subscribing to ssl/mqtts” followed by “Subscribe request sent”

I checked the sample application and found that if the connect was successful the application would then try and subscribe to a topic that didn’t exist.

mqtt.onConnected([]{
  Serial.println("[MQTT] Connected event");

   mqttReady = true;
/*
Serial.println("[MQTT] Subscribing to ssl/mqtt5");
if (mqtt.subscribe("ssl/mqtt5", 1, true)) {
  Serial.println("[MQTT] Subscribe request sent");
} else {
  Serial.println("[MQTT] Subscribe request failed");
}
*/

I commented out that code and the application started without any messages

Just to make sure I checked that the message count in the Azure Storage Queue was increasing and the payload client ID matched my device

Yet again a couple of hours lost from my life which I can never get back

Azure Event Grid esp-mqtt-arduino Client – Finding fail

Still couldn’t figure out why my code was failing so I built a test harness which connected to the wifi, set the time with the Network Time Protocol(NTP), established a Transport Layer Security(TLS) connection with the Azure Event Grid MQTT Broker then finally Authenticated (using Client Certificate authentication). Basically, it was The joy of certs without the Arduino PubSubClient library and with authentication

/*
  Azure Event Grid MQTT Endpoint Probe with mTLS
  - Wi-Fi connect
  - SNTP time sync
  - DNS resolve
  - TCP reachability (port 8883)
  - TLS (server-only) handshake using CRT bundle (or custom CA)
  - TLS (mTLS) handshake with client certificate & private key

  Notes:
    - Client certificate must be PEM and match private key.
    - Private key must be PEM and UNENCRYPTED (no passphrase).
    - SNI uses HOSTNAME automatically; do NOT use raw IP.
*/
#include <Arduino.h>
#include <WiFi.h>
#include <WiFiClient.h>
#include <WiFiClientSecure.h>

#include <../constants.h>
#include <../secrets.h>

extern "C" {
  #include <lwip/netdb.h>
  #include <lwip/sockets.h>
  #include <lwip/inet.h>
  #include <lwip/errno.h>
  #include <time.h>
}
static const char* HOSTNAME  = "ThisIsNotTheMQTTBrokerYouAreLookingFor.newzealandnorth-1.ts.eventgrid.azure.net";
static const uint16_t PORT   = 8883;

// Time servers (for TLS validity window)
static const char* NTP_1 = "pool.ntp.org";
static const char* NTP_2 = "time.cloudflare.com";

static const char* errnoName(int e) {
  switch (e) {
    case 5:   return "EIO";
    case 101: return "ENETUNREACH";
    case 104: return "ECONNRESET";
    case 110: return "ETIMEDOUT";
    case 111: return "ECONNREFUSED";
    case 113: return "EHOSTUNREACH";
    default:  return "?";
  }
}


bool waitForWifi(uint32_t timeout_ms = 20000) {
  uint32_t start = millis();
  Serial.printf("[WiFi] Connecting to '%s'...\n", WIFI_SSID);
  WiFi.begin(WIFI_SSID, WIFI_PASSWORD);
  while (WiFi.status() != WL_CONNECTED && (millis() - start) < timeout_ms) {
    delay(250);
    Serial.print(".");
  }
  Serial.println();
  return WiFi.status() == WL_CONNECTED;
}


void syncTime() {
  configTime(0, 0, NTP_1, NTP_2);
  Serial.println("[NTP] Syncing time...");
  for (int i = 0; i < 20; ++i) {
    time_t now = time(nullptr);
    if (now > 1609459200) { // > Jan 1, 2021
      Serial.printf("[NTP] OK (unix=%ld)\n", (long)now);
      return;
    }
    delay(500);
  }
  Serial.println("[NTP] Time sync may have failed; continuing.");
}

bool probeDNS(const char* host, char outIp[16]) {
  struct addrinfo hints = {};
  hints.ai_family = AF_INET; // IPv4
  struct addrinfo* res = nullptr;

  Serial.printf("[DNS] Resolving %s...\n", host);
  int rc = getaddrinfo(host, NULL, &hints, &res);
  Serial.printf("[DNS] getaddrinfo rc=%d\n", rc);
  if (rc != 0 || !res) {
    Serial.println("[DNS] FAILED");
    return false;
  }
  struct sockaddr_in* sin = (struct sockaddr_in*)res->ai_addr;
  inet_ntop(AF_INET, &sin->sin_addr, outIp, 16);
  Serial.printf("[DNS] %s -> %s\n", host, outIp);
  freeaddrinfo(res);
  return true;
}


bool probeTCP(const char* host, uint16_t port, uint32_t timeout_ms = 5000) {
  WiFiClient cli;
  cli.setTimeout(timeout_ms);
  Serial.printf("[TCP] Connecting to %s:%u ...\n", host, port);
  if (!cli.connect(host, port)) {
    Serial.printf("[TCP] connect() FAILED\n");
    return false;
  }
  Serial.println("[TCP] Connected (no TLS). Closing (probe only).");
  cli.stop();
  return true;
}


bool probeTLS(const char* host, uint16_t port, uint32_t timeout_ms = 7000) {
  WiFiClientSecure tls;
  tls.setTimeout(timeout_ms);

  tls.setCACert(CA_ROOT_PEM);  

  Serial.printf("[TLS] Handshake to %s:%u ...\n", host, port);
  if (!tls.connect(host, port)) {
    int e = errno;
    Serial.printf("[TLS] connect() FAILED errno=%d (%s)\n", e, errnoName(e));
    return false;
  }
  Serial.println("[TLS] Handshake OK (server-only TLS)");
  tls.stop();
  return true;
}

bool probeMTLS(const char* host, uint16_t port, uint32_t timeout_ms = 8000) {
  WiFiClientSecure tls;
  tls.setTimeout(timeout_ms);

  tls.setCACert(CA_ROOT_PEM);
  tls.setCertificate(CLIENT_CERT_PEM);
  tls.setPrivateKey(CLIENT_KEY_PEM);

  Serial.printf("[mTLS] Handshake to %s:%u with client cert ...\n", host, port);
  if (!tls.connect(host, port)) {
    int e = errno;
    Serial.printf("[mTLS] connect() FAILED errno=%d (%s)\n", e, errnoName(e));
    Serial.println("[mTLS] If errno=ETIMEDOUT/ECONNRESET, server may be closing due to cert policy mismatch.");
    return false;
  }
  Serial.println("[mTLS] Handshake OK (client authenticated)");
  tls.stop();
  return true;
}

void setup() {
  Serial.begin(9600);
  delay(5000);
  Serial.println();
  Serial.println("==== Azure Event Grid MQTT Probe (mTLS) ====");

  WiFi.mode(WIFI_STA);

  if (!waitForWifi()) {
    Serial.println("[WiFi] FAILED to connect within timeout");
  } else {
    Serial.printf("[WiFi] Connected. IP=%s  RSSI=%d dBm\n",
                  WiFi.localIP().toString().c_str(), WiFi.RSSI());
  }

  // TLS sanity: time
  syncTime();

  // DNS
  char ip[16] = {0};
  bool dnsOk = probeDNS(HOSTNAME, ip);

  // TCP reachability
  bool tcpOk = probeTCP(HOSTNAME, PORT);

  // TLS (server-only)
  bool tlsOk = probeTLS(HOSTNAME, PORT);

  // TLS (mTLS with client cert/key)
  bool mtlsOk = probeMTLS(HOSTNAME, PORT);

  Serial.println("==== Summary ====");
  Serial.printf("DNS:  %s\n", dnsOk  ? "OK" : "FAILED");
  Serial.printf("TCP:  %s\n", tcpOk  ? "OK" : "FAILED");
  Serial.printf("TLS:  %s\n", tlsOk  ? "OK" : "FAILED");
  Serial.printf("mTLS: %s\n", mtlsOk ? "OK" : "FAILED");
  Serial.println("=================");

  Serial.println("If mTLS=FAILED, check: correct cert/key pair, chain/trust CA, and namespace mTLS policy.");
}

void loop() {
  delay(1000);
}

The test harness worked which meant the issue was with my “re-factoring” of the BasicMqtt5_cert example.

Azure Event Grid esp-mqtt-arduino Client – Hours of fail

I wanted to get other Arduino base clients (e.g. my SeeedStudio XiaoESP32S3) for Azure Event Grid MQTT Broker working (for MQTT 5 support) so installed the esp-mqtt-arduino library.

The library doesn’t support client authentication with certificates, so I added two methods setClientCert and setClientKey to the esp-mqtt-arduino.h and esp-mqtt-arduino.cpp files

class Mqtt5ClientESP32 {
   public:
   Mqtt5ClientESP32();
   ~Mqtt5ClientESP32();
//...
  void useCrtBundle(bool enable = true);
  void setCACert(const char* cert, size_t len = 0);
  void setClientCert(const char* cert, size_t len = 0);
  void setClientKey(const char* key, size_t len = 0);  
  void setInsecure(bool enable = true);
  void setKeepAlive(uint16_t seconds);
private:
void Mqtt5ClientESP32::setClientCert(const char* cert, size_t len)
{
  insecure_ = false;
  cfg_.credentials.authentication.certificate = cert;
  if (cert) {
    cfg_.credentials.authentication.certificate_len = len ? len : strlen(cert) + 1;
  } else {
    cfg_.credentials.authentication.certificate_len = 0;
  }  
  cfg_.broker.verification.skip_cert_common_name_check = false;  
}

void Mqtt5ClientESP32::setClientKey(const char* key, size_t len)
{
  insecure_ = false;
  cfg_.credentials.authentication.key = key;
  if (key) {
    cfg_.credentials.authentication.key_len = len ? len : strlen(key) + 1;
  } else {
    cfg_.credentials.authentication.key_len = 0;
  } 
  cfg_.broker.verification.skip_cert_common_name_check = false;  
}

I had started with the basic_mqtt5_cert example stripping it back to the bare minimum hacking out all the certificate bundle support et.c

#include <WiFi.h>
#include <esp-mqtt-arduino.h>
#include <esp_log.h>
#include "sdkconfig.h"
#include "../secrets.h"
#include "../constants.h"

Mqtt5ClientESP32 mqtt;

volatile bool mqttReady = false;
volatile bool mqttSubscribed = false;
void setup() {
  Serial.begin(9600);
  delay(5000);
  Serial.setDebugOutput(true);
  Serial.println("[BOOT] Starting MQTT5 demo");

  esp_log_level_set("*", ESP_LOG_INFO);
  esp_log_level_set("MQTT_CLIENT", ESP_LOG_VERBOSE);

  WiFi.onEvent([](WiFiEvent_t event, WiFiEventInfo_t info){
    (void)info;
    Serial.printf("[WiFi event] id=%d\n", event);
  });

  Serial.printf("[WiFi] Connecting to %s\n", WIFI_SSID);
  WiFi.begin(WIFI_SSID, WIFI_PASSWORD);

  uint8_t attempts = 0;
  while (WiFi.status() != WL_CONNECTED) {
    Serial.printf("[WiFi] status=%d attempt=%u\n", WiFi.status(), attempts++);
    delay(500);
  }
  Serial.print("[WiFi] Connected, IP: ");
  Serial.println(WiFi.localIP());

  // Sync time for TLS
  Serial.println("\[NTP] synchronising");
  configTime(0, 0, "pool.ntp.org", "time.nist.gov");
  Serial.print("*");
  while (time(nullptr) < 100000) {
    delay(500);
    Serial.print("*");
  }
  Serial.println("\[NTP]  synchronised");

  Serial.printf("[MQTT] Init broker %s as %s\n", MQTT_SERVER_URL,MQTT_CLIENTID);
  mqtt.begin(MQTT_SERVER_URL, MQTT_CLIENTID);
  mqtt.setKeepAlive(45);

  mqtt.setCACert(CA_ROOT_PEM); 
  mqtt.setClientCert(CLIENT_CERT_PEM);
  mqtt.setClientKey(CLIENT_KEY_PEM);
  mqtt.setInsecure(false);

  mqtt.onMessage([](const char* topic, size_t topic_len, const uint8_t* data, size_t len){
    Serial.printf("[MSG] %.*s => %.*s\n", (int)topic_len, topic, (int)len, (const char*)data);
  });
  mqtt.onConnected([]{
    Serial.println("[MQTT] Connected event");
    mqttReady = true;
    Serial.println("[MQTT] Subscribing to ssl/mqtt5");
    if (mqtt.subscribe("ssl/mqtt5", 1, true)) {
      Serial.println("[MQTT] Subscribe request sent");
    } else {
      Serial.println("[MQTT] Subscribe request failed");
    }
  });

  mqtt.onDisconnected([]{
    Serial.println("[MQTT] Disconnected event");
    mqttReady = false;
  });

  Serial.println("[MQTT] Connecting...");
  if (!mqtt.connect()) {
    Serial.println("[MQTT] Connect start failed");
  }
}

void loop() {
  static unsigned long lastPublishMs = 0;
  const unsigned long now = millis();

  if (mqttReady && (now - lastPublishMs) >= 60000) {
    const char* msg = "Hello from Arduino MQTT5 ESP32!";
    Serial.println("[MQTT] Publishing demo message");
    if (mqtt.publish(MQTT_TOPIC_PUBLISH, (const uint8_t*)msg, strlen(msg))) {
      Serial.println("[MQTT] Publish queued (next in ~60s)");
    } else {
      Serial.println("[MQTT] Publish failed");
    }
    lastPublishMs = now;
  }

  delay(10);
}

It was important to put the setClientCert & setClient after the mqtt.begin because it resets the configuration

void Mqtt5ClientESP32::begin(const char* uri, const char* client_id,
                             const char* user, const char* pass, bool use_v5) {
  connected_ = false;
  insecure_ = false;
  cfg_.broker.address.uri = uri;
  if (client_id) cfg_.credentials.client_id = client_id;
  if (user)      cfg_.credentials.username  = user;
  if (pass)      cfg_.credentials.authentication.password = pass;

  cfg_.broker.verification.use_global_ca_store = false;
  cfg_.broker.verification.certificate = nullptr;
  cfg_.broker.verification.certificate_len = 0;
  cfg_.broker.verification.skip_cert_common_name_check = false;
  
  cfg_.session.last_will.topic  = "devices/esp32/lwt";
  cfg_.session.last_will.msg    = "offline";
  cfg_.session.last_will.qos    = 1;
  cfg_.session.last_will.retain = true;

cfg_.session.protocol_ver = 
#if CONFIG_MQTT_PROTOCOL_5
      use_v5 ? MQTT_PROTOCOL_V_5 : MQTT_PROTOCOL_V_3_1_1;
#else
      MQTT_PROTOCOL_V_3_1_1;
  (void)use_v5;  // MQTT v5 support disabled at build time
#endif
}

I tried increasing the log levels to get more debugging information, adding delays on startup to make it easier to see what was going on, trying different options of protocol support.

After hours of trying I gave up.

Azure Event Grid Server Certificate Validation

Over the last couple of weekends I had been trying to get a repeatable process for extracting the X509 certificate information in the correct structure so my Arduino application could connect to Azure Event Grid. The first step was to get the certificate chain for my Azure Event Grid MQTT Broker with openssl

openssl s_client -connect YourNameSpaceHere.newzealandnorth-1.ts.eventgrid.azure.net:443 -showcerts

The CN: CN=DigiCert Global Root G3 and the wildcard CN=*.eventgrid.azure.net certificates were “concatenated” in the constants header file which is included in the main program file. The format of the certificate chain is described in the comments. Avoid blank lines, “rogue” spaces or other formatting as these may cause the WiFiClientSecure Mbed TLS implementation to fail.

/*
Minimalist ESP32 + Azure Event Grid MQTT Event Grid broker namespace certificate validation
copyright (c) November 2025, devMobile Software
*/
#include <WiFi.h>
#include <WiFiClientSecure.h>
#include "secrets.h"
#include "constants.h"

// --- Wi-Fi ---
//const char* WIFI_SSID     = "";
//const char* WIFI_PASSWORD = "";

//const char* MQTT_SERVER = "YourNamespace.newzealandnorth-1.ts.eventgrid.azure.net";
const uint16_t MQTT_PORT = 8883;

/*
// The certificate that is used to authenticate the MQTT Broker
const char CA_ROOT_PEM[] PROGMEM = R"PEM(
-----BEGIN CERTIFICATE-----
MIIGdTCCBfugAwIBAgITMwAC8tqK8+gk3Ll5FwAAAALy2jAKBggqhkjOPQQDAzBd
....
      Thumbprint: 56D955C849887874AA1767810366D90ADF6C8536
      CN: CN=Microsoft Azure ECC TLS Issuing CA 03
      CN=*.eventgrid.azure.net      
....
4ZWZhnNydNZmt4H/7KAd5/UaIP/IUI/xBg==
-----END CERTIFICATE-----
-----BEGIN CERTIFICATE-----
MIIDXTCCAuOgAwIBAgIQAVKe6DaPC11yukM+LY6mLTAKBggqhkjOPQQDAzBhMQsw
....
      Thumbprint: 7E04DE896A3E666D00E687D33FFAD93BE83D349E
      CN: CN=DigiCert Global Root G3
....
MGHYkSqHik6yPbKi1OaJkVl9grldr+Y+z+jgUwWIaJ6ljXXj8cPXpyFgz3UEDnip
Eg==
-----END CERTIFICATE-----
)PEM";
*/

WiFiClientSecure secureClient;

void setup() {
  Serial.begin(9600);
  delay(2000);
  Serial.println("\nServerCertificateValidationClient starting");

  struct tm timeinfo;
  if (getLocalTime(&timeinfo)) {
    Serial.printf("Startup DateTime: %04d-%02d-%02d %02d:%02d:%02d\n", timeinfo.tm_year + 1900, timeinfo.tm_mon + 1, timeinfo.tm_mday, timeinfo.tm_hour, timeinfo.tm_min, timeinfo.tm_sec);
  }

  // Connect to WiFi
  Serial.println("WiFi connecting");
  WiFi.begin(WIFI_SSID, WIFI_PASSWORD);
  Serial.print("*");
  while (WiFi.status() != WL_CONNECTED) {
    delay(500);
    Serial.print("*");
  }
  Serial.println("\nWiFi connected");

  if (getLocalTime(&timeinfo)) {
    Serial.printf("Wifi DateTime: %04d-%02d-%02d %02d:%02d:%02d\n", timeinfo.tm_year + 1900, timeinfo.tm_mon + 1, timeinfo.tm_mday, timeinfo.tm_hour, timeinfo.tm_min, timeinfo.tm_sec);
  }

  // Sync time for TLS
  Serial.println("\nTime synchronising");
  configTime(0, 0, "pool.ntp.org", "time.nist.gov");
  Serial.print("*");
  while (time(nullptr) < 100000) {
    delay(500);
    Serial.print("*");
  }
  Serial.println("\nTime synchronised");

  if (getLocalTime(&timeinfo)) {
    Serial.printf("NTP DateTime: %04d-%02d-%02d %02d:%02d:%02d\n", timeinfo.tm_year + 1900, timeinfo.tm_mon + 1, timeinfo.tm_mday, timeinfo.tm_hour, timeinfo.tm_min, timeinfo.tm_sec);
  }

  Serial.println("\nValidating ServerFQDN-Certificate combination");
  secureClient.setCACert(CA_ROOT_PEM);
  Serial.print("*");
  while (!secureClient.connect(MQTT_SERVER, MQTT_PORT)) {
    delay(500);
    Serial.print("*");
  }
  Serial.println("\nTLS Connected");
}

void loop() {
  Serial.print("x");
  delay(5000);
}

After a hard reset the WiFiClientSecure connect failed because the device time had not been initialised so the device/server time offset was too large (see rfc9325)

After a “hard” reset the Network Time Protocol(NTP) client was used to set the device time.

After a “soft” reset the Network Time Protocol(NTP) client did not have to be called.

Azure Event Grid MQTT-Certificates

When configuring Root, Intermediate and Device certificates for my Azure Event Grid Devices using the smallstep step-ca or OpenSSL I made mistakes/typos which broke my deployment and in the end I was copying and pasting commands from Windows Notepad.

For one test deployment it took me an hour to generate the Root, Intermediate and a number of Devices certificates which was a waste of time. At this point I decided investigate writing some applications to simplify the process.

After some searching I stumbled across CREATING CERTIFICATES FOR X.509 SECURITY IN AZURE IOT HUB USING .NET CORE by Damien Bod which showed how to generate certificates for Azure IoT Hub solutions using his NuGet package Certificate Manager.

The AzureIoTHubDps repository had a sample showing how to generate the certificate chain for Azure IoT Hub devices. It worked really well but I accidentally overwrote my Root and Intermediate certificates, there were some “magic numbers” and hard coded passwords (it was a sample) so I decided to “chop” the sample up into three command line applications.

static void Main(string[] args)
{
   var serviceProvider = new ServiceCollection()
         .AddCertificateManager()
         .BuildServiceProvider();

   // load the app settings into configuration
   var configuration = new ConfigurationBuilder()
         .AddJsonFile("appsettings.json", false, true)
         .AddUserSecrets<Program>()
   .Build();

   _applicationSettings = configuration.GetSection("ApplicationSettings").Get<Model.ApplicationSettings>();
//------
   Console.WriteLine($"validFrom:{validFrom} ValidTo:{validTo}");

   var serverRootCertificate = serviceProvider.GetService<CreateCertificatesClientServerAuth>();

   var root = serverRootCertificate.NewRootCertificate(
         new DistinguishedName { 
               CommonName = _applicationSettings.CommonName,
               Organisation = _applicationSettings.Organisation,
               OrganisationUnit = _applicationSettings.OrganisationUnit,
               Locality = _applicationSettings.Locality,
               StateProvince  = _applicationSettings.StateProvince,
               Country = _applicationSettings.Country
         },
         new ValidityPeriod { 
         ValidFrom = validFrom,
         ValidTo = validTo,
         },
         _applicationSettings.PathLengthConstraint,
         _applicationSettings.DnsName);
   root.FriendlyName = _applicationSettings.FriendlyName;

   Console.Write("PFX Password:");
   string password = Console.ReadLine();
   if ( String.IsNullOrEmpty(password))
   {
      Console.WriteLine("PFX Password invalid");
      return;
   }

   var exportCertificate = serviceProvider.GetService<ImportExportCertificate>();

   var rootCertificatePfxBytes = exportCertificate.ExportRootPfx(password, root);
   File.WriteAllBytes(_applicationSettings.RootCertificateFilePath, rootCertificatePfxBytes);

   Console.WriteLine($"Root certificate file:{_applicationSettings.RootCertificateFilePath}");
   Console.WriteLine("press enter to exit");
   Console.ReadLine();
}

The application’s configuration was split between application settings file(certificate file paths, validity periods, Organisation etc.) or entered at runtime ( certificate filenames, passwords etc.) The first application generates a Root Certificate using the distinguished name information from the application settings, plus file names and passwords entered by the user.

Root Certificate generation application output

The second application generates an Intermediate Certificate using the Root Certificate, the distinguished name information from the application settings, plus file names and passwords entered by the user.

static void Main(string[] args)
{
   var serviceProvider = new ServiceCollection()
         .AddCertificateManager()
         .BuildServiceProvider();

   // load the app settings into configuration
   var configuration = new ConfigurationBuilder()
         .AddJsonFile("appsettings.json", false, true)
         .AddUserSecrets<Program>()
   .Build();

   _applicationSettings = configuration.GetSection("ApplicationSettings").Get<Model.ApplicationSettings>();
//------
   Console.WriteLine($"validFrom:{validFrom} be after ValidTo:{validTo}");

   Console.WriteLine($"Root Certificate file:{_applicationSettings.RootCertificateFilePath}");

   Console.Write("Root Certificate Password:");
   string rootPassword = Console.ReadLine();
   if (String.IsNullOrEmpty(rootPassword))
   {
      Console.WriteLine("Fail");
      return;
   }
   var rootCertificate = new X509Certificate2(_applicationSettings.RootCertificateFilePath, rootPassword);

   var intermediateCertificateCreate = serviceProvider.GetService<CreateCertificatesClientServerAuth>();

   var intermediateCertificate = intermediateCertificateCreate.NewIntermediateChainedCertificate(
         new DistinguishedName
         {
            CommonName = _applicationSettings.CommonName,
            Organisation = _applicationSettings.Organisation,
            OrganisationUnit = _applicationSettings.OrganisationUnit,
            Locality = _applicationSettings.Locality,
            StateProvince = _applicationSettings.StateProvince,
            Country = _applicationSettings.Country
         },
      new ValidityPeriod
      {
         ValidFrom = validFrom,
         ValidTo = validTo,
      },
            _applicationSettings.PathLengthConstraint,
            _applicationSettings.DnsName, rootCertificate);
      intermediateCertificate.FriendlyName = _applicationSettings.FriendlyName;

   Console.Write("Intermediate certificate Password:");
   string intermediatePassword = Console.ReadLine();
   if (String.IsNullOrEmpty(intermediatePassword))
   {
      Console.WriteLine("Fail");
      return;
   }

   var importExportCertificate = serviceProvider.GetService<ImportExportCertificate>();

   Console.WriteLine($"Intermediate PFX file:{_applicationSettings.IntermediateCertificatePfxFilePath}");
   var intermediateCertificatePfxBtyes = importExportCertificate.ExportChainedCertificatePfx(intermediatePassword, intermediateCertificate, rootCertificate);
   File.WriteAllBytes(_applicationSettings.IntermediateCertificatePfxFilePath, intermediateCertificatePfxBtyes);

   Console.WriteLine($"Intermediate CER file:{_applicationSettings.IntermediateCertificateCerFilePath}");
   var intermediateCertificatePemText = importExportCertificate.PemExportPublicKeyCertificate(intermediateCertificate);
   File.WriteAllText(_applicationSettings.IntermediateCertificateCerFilePath, intermediateCertificatePemText);

   Console.WriteLine("press enter to exit");
   Console.ReadLine();
}
Intermediate Certificate generation application output
Uploading the Intermediate certificate to Azure Event Grid

The third application generates Device Certificates using the Intermediate Certificate, distinguished name information from the application settings, plus device id, file names and passwords entered by the user.

static void Main(string[] args)
{
   var serviceProvider = new ServiceCollection()
         .AddCertificateManager()
         .BuildServiceProvider();

   // load the app settings into configuration
   var configuration = new ConfigurationBuilder()
         .AddJsonFile("appsettings.json", false, true)
         .AddUserSecrets<Program>()
   .Build();

   _applicationSettings = configuration.GetSection("ApplicationSettings").Get<Model.ApplicationSettings>();
//------
   Console.WriteLine($"validFrom:{validFrom} ValidTo:{validTo}");

   Console.WriteLine($"Intermediate PFX file:{_applicationSettings.IntermediateCertificateFilePath}");

   Console.Write("Intermediate PFX Password:");
   string intermediatePassword = Console.ReadLine();
   if (String.IsNullOrEmpty(intermediatePassword))
   {
      Console.WriteLine("Intermediate PFX Password invalid");
      return;
   }
   var intermediate = new X509Certificate2(_applicationSettings.IntermediateCertificateFilePath, intermediatePassword);

   Console.Write("Device ID:");
   string deviceId = Console.ReadLine();
   if (String.IsNullOrEmpty(deviceId))
   {
      Console.WriteLine("Device ID invalid");
      return;
   }

   var createClientServerAuthCerts = serviceProvider.GetService<CreateCertificatesClientServerAuth>();

   var device = createClientServerAuthCerts.NewDeviceChainedCertificate(
         new DistinguishedName
         {
            CommonName = deviceId,
            Organisation = _applicationSettings.Organisation,
            OrganisationUnit = _applicationSettings.OrganisationUnit,
            Locality = _applicationSettings.Locality,
            StateProvince = _applicationSettings.StateProvince,
            Country = _applicationSettings.Country
         },
      new ValidityPeriod
      {
         ValidFrom = validFrom,
         ValidTo = validTo,
      },
      deviceId, intermediate);
   device.FriendlyName = deviceId;

   Console.Write("Device PFX Password:");
   string devicePassword = Console.ReadLine();
   if (String.IsNullOrEmpty(devicePassword))
   {
      Console.WriteLine("Fail");
      return;
   }

   var importExportCertificate = serviceProvider.GetService<ImportExportCertificate>();

   string devicePfxPath = string.Format(_applicationSettings.DeviceCertificatePfxFilePath, deviceId);

   Console.WriteLine($"Device PFX file:{devicePfxPath}");
   var deviceCertificatePath = importExportCertificate.ExportChainedCertificatePfx(devicePassword, device, intermediate);
   File.WriteAllBytes(devicePfxPath,  deviceCertificatePath);

   Console.WriteLine("press enter to exit");
   Console.ReadLine();
}
Device Certificate generation application output
Uploading the Intermediate certificate to Azure Event Grid

These applications wouldn’t have been possible without Damien Bod’s CREATING CERTIFICATES FOR X.509 SECURITY IN AZURE IOT HUB USING .NET CORE blog post, and his Certificate Manager NuGet package.