diff --git a/libraries/WiFiClientSecure/examples/WiFiClientSecureProtocolUpgrade/.skip.esp32h2 b/libraries/WiFiClientSecure/examples/WiFiClientSecureProtocolUpgrade/.skip.esp32h2
new file mode 100644
index 00000000000..e69de29bb2d
diff --git a/libraries/WiFiClientSecure/examples/WiFiClientSecureProtocolUpgrade/WiFiClientSecureProtocolUpgrade.ino b/libraries/WiFiClientSecure/examples/WiFiClientSecureProtocolUpgrade/WiFiClientSecureProtocolUpgrade.ino
new file mode 100644
index 00000000000..06c19d105c4
--- /dev/null
+++ b/libraries/WiFiClientSecure/examples/WiFiClientSecureProtocolUpgrade/WiFiClientSecureProtocolUpgrade.ino
@@ -0,0 +1,176 @@
+/* STARTSSL example
+
+   Inline upgrading from a clear-text connection to an SSL/TLS connection.
+
+   Some protocols such as SMTP, XMPP, Mysql, Postgress and others allow, or require,
+   that you start the connection without encryption; and then send a command to switch
+   over to encryption.
+
+   E.g. a typical SMTP submission would entail a dialogue such as this:
+
+   1. client connects to server in the clear
+   2. server says hello
+   3. client sents a EHLO
+   4. server tells the client that it supports SSL/TLS
+   5. client sends a 'STARTTLS' to make use of this faciltiy
+   6. client/server negiotiate a SSL or TLS connection.
+   7. client sends another EHLO
+   8. server now tells the client what (else) is supported; such as additional authentication options.
+   ... conversation continues encrypted.
+
+   This can be enabled in WiFiClientSecure by telling it to start in plaintext:
+
+          client.setPlainStart();
+
+   and client is than a plain, TCP, connection (just as WiFiClient would be); until the client calls
+   the method:
+
+          client.startTLS(); // returns zero on error; non zero on success.
+
+    After which things switch to TLS/SSL.
+*/
+
+#include <WiFiClientSecure.h>
+
+#ifndef WIFI_NETWORK
+#define WIFI_NETWORK "YOUR Wifi SSID"
+#endif
+
+#ifndef WIFI_PASSWD
+#define WIFI_PASSWD "your-secret-password"
+#endif
+
+#ifndef SMTP_HOST
+#define SMTP_HOST "smtp.gmail.com"
+#endif
+
+#ifndef SMTP_PORT
+#define SMTP_PORT (587) // Standard (plaintext) submission port
+#endif
+
+const char* ssid = WIFI_NETWORK;       // your network SSID (name of wifi network)
+const char* password = WIFI_PASSWD;    // your network password
+const char* server = SMTP_HOST;        // Server URL
+const int submission_port = SMTP_PORT; // submission port.
+
+WiFiClientSecure client;
+
+static bool readAllSMTPLines();
+
+void setup() {
+  int ret;
+  //Initialize serial and wait for port to open:
+  Serial.begin(115200);
+  delay(100);
+
+  Serial.print("Attempting to connect to SSID: ");
+  Serial.print(ssid);
+  WiFi.begin(ssid, password);
+
+  // attempt to connect to Wifi network:
+  while (WiFi.status() != WL_CONNECTED) {
+    Serial.print(".");
+    // wait 1 second for re-trying
+    delay(1000);
+  }
+
+  Serial.print("Connected to ");
+  Serial.println(ssid);
+
+  Serial.printf("\nStarting connection to server: %s:%d\n", server, submission_port);
+
+
+  // skip verification for this demo. In production one should at the very least
+  // enable TOFU; or ideally hardcode a (CA) certificate that is trusted.
+  client.setInsecure();
+
+  // Enable a plain-test start.
+  client.setPlainStart();
+
+  if (!client.connect(server, SMTP_PORT)) {
+    Serial.println("Connection failed!");
+    return;
+  };
+
+  Serial.println("Connected to server (in the clear, in plaintest)");
+
+  if (!readAllSMTPLines()) goto err;
+
+  Serial.println("Sending  : EHLO\t\tin the clear");
+  client.print("EHLO there\r\n");
+
+  if (!readAllSMTPLines()) goto err;
+
+  Serial.println("Sending  : STARTTLS\t\tin the clear");
+  client.print("STARTTLS\r\n");
+
+  if (!readAllSMTPLines()) goto err;
+
+  Serial.println("Upgrading connection to TLS");
+  if ((ret=client.startTLS()) <= 0) {
+    Serial.printf("Upgrade connection failed: err %d\n", ret);
+    goto err;
+  }
+
+  Serial.println("Sending  : EHLO again\t\tover the now encrypted connection");
+  client.print("EHLO again\r\n");
+
+  if (!readAllSMTPLines()) goto err;
+
+  // normally, as this point - we'd be authenticating and then be submitting
+  // an email. This has been left out of this example.
+  
+  Serial.println("Sending  : QUIT\t\t\tover the now encrypted connection");
+  client.print("QUIT\r\n");
+
+  if (!readAllSMTPLines()) goto err;
+
+  Serial.println("Completed OK\n");
+err:
+  Serial.println("Closing connection");
+  client.stop();
+}
+
+// SMTP command repsponse start with three digits and a space;
+// or, for continuation, with three digits and a '-'.
+static bool readAllSMTPLines() {
+  String s = "";
+  int i;
+
+  // blocking read; we cannot rely on a timeout
+  // of a WiFiClientSecure read; as it is non
+  // blocking.
+  const unsigned long timeout = 15 * 1000;
+  unsigned long start = millis(); // the timeout is for the entire CMD block response; not per character/line.
+  while (1) {
+    while ((i = client.available()) == 0 && millis() - start < timeout) {
+      /* .. wait */
+    };
+    if (i == 0) {
+      Serial.println("Timeout reading SMTP response");
+      return false;
+    };
+    if (i < 0)
+      break;
+
+    i = client.read();
+    if (i < 0)
+      break;
+
+    if (i > 31 && i < 128) s += (char)i;
+    if (i == 0x0A) {
+      Serial.print("Receiving: ");
+      Serial.println(s);
+      if (s.charAt(3) == ' ')
+        return true;
+      s = "";
+    }
+  }
+  Serial.printf("Error reading SMTP command response line: %d\n", i);
+  return false;
+}
+
+void loop() {
+  // do nothing
+}
+
diff --git a/libraries/WiFiClientSecure/src/WiFiClientSecure.cpp b/libraries/WiFiClientSecure/src/WiFiClientSecure.cpp
index 2f9da58f9ad..ebecf94ffb6 100644
--- a/libraries/WiFiClientSecure/src/WiFiClientSecure.cpp
+++ b/libraries/WiFiClientSecure/src/WiFiClientSecure.cpp
@@ -143,9 +143,16 @@ int WiFiClientSecure::connect(const char *host, uint16_t port, const char *CA_ce
 int WiFiClientSecure::connect(IPAddress ip, uint16_t port, const char *host, const char *CA_cert, const char *cert, const char *private_key)
 {
     int ret = start_ssl_client(sslclient, ip, port, host, _timeout, CA_cert, _use_ca_bundle, cert, private_key, NULL, NULL, _use_insecure, _alpn_protos);
+
+    if (ret >=0 && ! _stillinPlainStart)
+        ret = ssl_starttls_handshake(sslclient);
+    else
+        log_i("Actual TLS start posponed.");
+
     _lastError = ret;
+
     if (ret < 0) {
-        log_e("start_ssl_client: %d", ret);
+        log_e("start_ssl_client: connect failed: %d", ret);
         stop();
         return 0;
     }
@@ -153,6 +160,23 @@ int WiFiClientSecure::connect(IPAddress ip, uint16_t port, const char *host, con
     return 1;
 }
 
+int WiFiClientSecure::startTLS()
+{
+    int ret = 1;
+    if (_stillinPlainStart) {
+        log_i("startTLS: starting TLS/SSL on this dplain connection");
+        ret = ssl_starttls_handshake(sslclient);
+        if (ret < 0) {
+                log_e("startTLS: %d", ret);
+                stop();
+                return 0;
+        };
+        _stillinPlainStart = false;
+    } else 
+        log_i("startTLS: ignoring StartTLS - as we should be secure already");
+    return 1;
+}
+
 int WiFiClientSecure::connect(IPAddress ip, uint16_t port, const char *pskIdent, const char *psKey) {
     return connect(ip.toString().c_str(), port, pskIdent, psKey);
 }
@@ -167,7 +191,7 @@ int WiFiClientSecure::connect(const char *host, uint16_t port, const char *pskId
     int ret = start_ssl_client(sslclient, address, port, host, _timeout, NULL, false, NULL, NULL, pskIdent, psKey, _use_insecure, _alpn_protos);
     _lastError = ret;
     if (ret < 0) {
-        log_e("start_ssl_client: %d", ret);
+        log_e("start_ssl_client: connect failed %d", ret);
         stop();
         return 0;
     }
@@ -192,10 +216,7 @@ int WiFiClientSecure::read()
 {
     uint8_t data = -1;
     int res = read(&data, 1);
-    if (res < 0) {
-        return res;
-    }
-    return data;
+    return res < 0 ? res: data;
 }
 
 size_t WiFiClientSecure::write(const uint8_t *buf, size_t size)
@@ -203,6 +224,10 @@ size_t WiFiClientSecure::write(const uint8_t *buf, size_t size)
     if (!_connected) {
         return 0;
     }
+
+    if (_stillinPlainStart) 
+        return send_net_data(sslclient, buf, size);
+
     if(_lastWriteTimeout != _timeout){
         struct timeval timeout_tv;
         timeout_tv.tv_sec = _timeout / 1000;
@@ -212,9 +237,9 @@ size_t WiFiClientSecure::write(const uint8_t *buf, size_t size)
             _lastWriteTimeout = _timeout;
         }
     }
-
     int res = send_ssl_data(sslclient, buf, size);
     if (res < 0) {
+        log_e("Closing connection on failed write");
         stop();
         res = 0;
     }
@@ -223,6 +248,9 @@ size_t WiFiClientSecure::write(const uint8_t *buf, size_t size)
 
 int WiFiClientSecure::read(uint8_t *buf, size_t size)
 {
+    if(_stillinPlainStart) 
+        return  get_net_receive(sslclient, buf, size);
+
     if(_lastReadTimeout != _timeout){
         if(fd() >= 0){
             struct timeval timeout_tv;
@@ -235,7 +263,7 @@ int WiFiClientSecure::read(uint8_t *buf, size_t size)
         }
     }
 
-    int peeked = 0;
+    int peeked = 0, res = -1;
     int avail = available();
     if ((!buf && size) || avail <= 0) {
         return -1;
@@ -254,9 +282,10 @@ int WiFiClientSecure::read(uint8_t *buf, size_t size)
         buf++;
         peeked = 1;
     }
-    
-    int res = get_ssl_receive(sslclient, buf, size);
+        res = get_ssl_receive(sslclient, buf, size);
+
     if (res < 0) {
+        log_e("Closing connection on failed read");
         stop();
         return peeked?peeked:res;
     }
@@ -265,12 +294,17 @@ int WiFiClientSecure::read(uint8_t *buf, size_t size)
 
 int WiFiClientSecure::available()
 {
-    int peeked = (_peek >= 0);
+    if (_stillinPlainStart) 
+        return peek_net_receive(sslclient,0);
+
+    int peeked = (_peek >= 0), res = -1;
     if (!_connected) {
         return peeked;
     }
-    int res = data_to_read(sslclient);
-    if (res < 0) {
+    res = data_to_read(sslclient);
+
+    if (res < 0 && !_stillinPlainStart) {
+        log_e("Closing connection on failed available check");
         stop();
         return peeked?peeked:res;
     }
@@ -406,3 +440,4 @@ int WiFiClientSecure::fd() const
 {
     return sslclient->socket;
 }
+
diff --git a/libraries/WiFiClientSecure/src/WiFiClientSecure.h b/libraries/WiFiClientSecure/src/WiFiClientSecure.h
index 8c130f450cc..31daebbdb42 100644
--- a/libraries/WiFiClientSecure/src/WiFiClientSecure.h
+++ b/libraries/WiFiClientSecure/src/WiFiClientSecure.h
@@ -34,6 +34,7 @@ class WiFiClientSecure : public WiFiClient
     int _peek = -1;
     int _timeout;
     bool _use_insecure;
+    bool _stillinPlainStart = false;
     const char *_CA_cert;
     const char *_cert;
     const char *_private_key;
@@ -78,6 +79,17 @@ class WiFiClientSecure : public WiFiClient
     bool verify(const char* fingerprint, const char* domain_name);
     void setHandshakeTimeout(unsigned long handshake_timeout);
     void setAlpnProtocols(const char **alpn_protos);
+
+    // Certain protocols start in plain-text; and then have the client
+    // give some STARTSSL command to `upgrade' the connection to TLS
+    // or SSL. Setting PlainStart to true (the default is false) enables
+    // this. It is up to the application code to then call 'startTLS()'
+    // at the right point to initialise the SSL or TLS upgrade.
+    
+    void setPlainStart() { _stillinPlainStart = true; };
+    bool stillInPlainStart() { return _stillinPlainStart; };
+    int startTLS();
+
     const mbedtls_x509_crt* getPeerCertificate() { return mbedtls_ssl_get_peer_cert(&sslclient->ssl_ctx); };
     bool getFingerprintSHA256(uint8_t sha256_result[32]) { return get_peer_fingerprint(sslclient, sha256_result); };
     int fd() const;
diff --git a/libraries/WiFiClientSecure/src/ssl_client.cpp b/libraries/WiFiClientSecure/src/ssl_client.cpp
index 8dcf05877ba..a4308abb1e8 100644
--- a/libraries/WiFiClientSecure/src/ssl_client.cpp
+++ b/libraries/WiFiClientSecure/src/ssl_client.cpp
@@ -55,8 +55,7 @@ void ssl_init(sslclient_context *ssl_client)
 
 int start_ssl_client(sslclient_context *ssl_client, const IPAddress& ip, uint32_t port, const char* hostname, int timeout, const char *rootCABuff, bool useRootCABundle, const char *cli_cert, const char *cli_key, const char *pskIdent, const char *psKey, bool insecure, const char **alpn_protos)
 {
-    char buf[512];
-    int ret, flags;
+    int ret;
     int enable = 1;
     log_v("Free internal heap before TLS %u", ESP.getFreeHeap());
 
@@ -226,6 +225,9 @@ int start_ssl_client(sslclient_context *ssl_client, const IPAddress& ip, uint32_
         return -1;
     }
 
+    // Note - this check for BOTH key and cert is relied on
+    // later during cleanup.
+    
     if (!insecure && cli_cert != NULL && cli_key != NULL) {
         mbedtls_x509_crt_init(&ssl_client->client_cert);
         mbedtls_pk_init(&ssl_client->client_key);
@@ -267,6 +269,13 @@ int start_ssl_client(sslclient_context *ssl_client, const IPAddress& ip, uint32_
     }
 
     mbedtls_ssl_set_bio(&ssl_client->ssl_ctx, &ssl_client->socket, mbedtls_net_send, mbedtls_net_recv, NULL );
+    return ssl_client->socket;
+}
+
+int ssl_starttls_handshake(sslclient_context *ssl_client)
+{
+    char buf[512];
+    int ret, flags;
 
     log_v("Performing the SSL/TLS handshake...");
     unsigned long handshake_start_time=millis();
@@ -280,7 +289,7 @@ int start_ssl_client(sslclient_context *ssl_client, const IPAddress& ip, uint32_
     }
 
 
-    if (cli_cert != NULL && cli_key != NULL) {
+    if (ssl_client->client_cert.version) {
         log_d("Protocol is %s Ciphersuite is %s", mbedtls_ssl_get_version(&ssl_client->ssl_ctx), mbedtls_ssl_get_ciphersuite(&ssl_client->ssl_ctx));
         if ((ret = mbedtls_ssl_get_record_expansion(&ssl_client->ssl_ctx)) >= 0) {
             log_d("Record expansion is %d", ret);
@@ -300,15 +309,16 @@ int start_ssl_client(sslclient_context *ssl_client, const IPAddress& ip, uint32_
         log_v("Certificate verified.");
     }
     
-    if (rootCABuff != NULL) {
+    if (ssl_client->ca_cert.version) {
         mbedtls_x509_crt_free(&ssl_client->ca_cert);
     }
 
-    if (cli_cert != NULL) {
+    // We know that we always have a client cert/key pair -- and we
+    // cannot look into the private client_key pk struct for newer
+    // versions of mbedtls. So rely on a public field of the cert
+    // and infer that there is a key too.
+    if (ssl_client->client_cert.version) {
         mbedtls_x509_crt_free(&ssl_client->client_cert);
-    }
-
-    if (cli_key != NULL) {
         mbedtls_pk_free(&ssl_client->client_key);
     }    
 
@@ -317,7 +327,6 @@ int start_ssl_client(sslclient_context *ssl_client, const IPAddress& ip, uint32_
     return ssl_client->socket;
 }
 
-
 void stop_ssl_socket(sslclient_context *ssl_client, const char *rootCABuff, const char *cli_cert, const char *cli_key)
 {
     log_v("Cleaning SSL connection.");
@@ -328,13 +337,13 @@ void stop_ssl_socket(sslclient_context *ssl_client, const char *rootCABuff, cons
     }
 
     // avoid memory leak if ssl connection attempt failed
-    //if (ssl_client->ssl_conf.ca_chain != NULL) {
+    // if (ssl_client->ssl_conf.ca_chain != NULL) {
         mbedtls_x509_crt_free(&ssl_client->ca_cert);
-    //}
-    //if (ssl_client->ssl_conf.key_cert != NULL) {
+    // }
+    // if (ssl_client->ssl_conf.key_cert != NULL) {
         mbedtls_x509_crt_free(&ssl_client->client_cert);
         mbedtls_pk_free(&ssl_client->client_key);
-    //}
+    // }
     mbedtls_ssl_free(&ssl_client->ssl_ctx);
     mbedtls_ssl_config_free(&ssl_client->ssl_conf);
     mbedtls_ctr_drbg_free(&ssl_client->drbg_ctx);
@@ -368,10 +377,8 @@ int data_to_read(sslclient_context *ssl_client)
 
 int send_ssl_data(sslclient_context *ssl_client, const uint8_t *data, size_t len)
 {
-    log_v("Writing HTTP request with %d bytes...", len); //for low level debug
-    int ret = -1;
-
     unsigned long write_start_time=millis();
+    int ret = -1;
 
     while ((ret = mbedtls_ssl_write(&ssl_client->ssl_ctx, data, len)) <= 0) {
         if((millis()-write_start_time)>ssl_client->socket_timeout) {
@@ -391,14 +398,60 @@ int send_ssl_data(sslclient_context *ssl_client, const uint8_t *data, size_t len
     return ret;
 }
 
-int get_ssl_receive(sslclient_context *ssl_client, uint8_t *data, int length)
+// Some protocols, such as SMTP, XMPP, MySQL/Posgress and various others
+// do a 'in-line' upgrade from plaintext to SSL or TLS (usually with some
+// sort of 'STARTTLS' textual command from client to sever). For this
+// we need to have access to the 'raw' socket; i.e. without TLS/SSL state
+// handling before the handshake starts; but after setting up the TLS
+// connection.
+//
+int peek_net_receive(sslclient_context *ssl_client, int timeout) {
+#if MBEDTLS_FIXED_LINKING_NET_POLL
+    int ret = mbedtls_net_poll((mbedtls_net_context*)ssl_client, MBEDTLS_NET_POLL_READ, timeout);
+    ret == MBEDTLS_NET_POLL_READ ? 1 : ret;
+#else
+    // We should be using mbedtls_net_poll(); which is part of mbedtls and
+    // included in the EspressifSDK. Unfortunately - it did not make it into
+    // the statically linked library file. So, for now, we replace it by
+    // substancially similar code.
+    //
+    struct timeval tv = { .tv_sec = timeout / 1000, .tv_usec = (timeout % 1000) * 1000 };
+
+    fd_set fdset;
+    FD_SET(ssl_client->socket, &fdset);
+
+    int ret = select(ssl_client->socket + 1, &fdset, nullptr, nullptr, timeout<0 ? nullptr : &tv);
+    if (ret < 0) {
+        log_e("select on read fd %d, errno: %d, \"%s\"", ssl_client->socket, errno, strerror(errno));
+        lwip_close(ssl_client->socket);
+        ssl_client->socket = -1;
+        return -1;
+    };
+#endif
+    return ret;
+};
+
+int get_net_receive(sslclient_context *ssl_client, uint8_t *data, int length)
 {
-    //log_d( "Reading HTTP response...");   //for low level debug
-    int ret = -1;
+   int ret = peek_net_receive(ssl_client,ssl_client->socket_timeout);
+   if (ret > 0)
+	ret = mbedtls_net_recv(ssl_client, data, length);
 
-    ret = mbedtls_ssl_read(&ssl_client->ssl_ctx, data, length);
+    // log_v( "%d bytes NET read of %d", ret, length);   //for low level debug
+    return ret;
+}
 
-    //log_v( "%d bytes read", ret);   //for low level debug
+int send_net_data(sslclient_context *ssl_client, const uint8_t *data, size_t len) {
+    int ret = mbedtls_net_send(ssl_client, data, len);
+    // log_v("Net sending %d btes->ret %d", len, ret); //for low level debug
+    return ret;
+}
+
+
+int get_ssl_receive(sslclient_context *ssl_client, uint8_t *data, int length)
+{
+    int ret = mbedtls_ssl_read(&ssl_client->ssl_ctx, data, length);
+    // log_v( "%d bytes SSL read", ret);   //for low level debug
     return ret;
 }
 
diff --git a/libraries/WiFiClientSecure/src/ssl_client.h b/libraries/WiFiClientSecure/src/ssl_client.h
index 69e49707cba..f42ad534139 100644
--- a/libraries/WiFiClientSecure/src/ssl_client.h
+++ b/libraries/WiFiClientSecure/src/ssl_client.h
@@ -31,10 +31,14 @@ typedef struct sslclient_context {
 
 void ssl_init(sslclient_context *ssl_client);
 int start_ssl_client(sslclient_context *ssl_client, const IPAddress& ip, uint32_t port, const char* hostname, int timeout, const char *rootCABuff, bool useRootCABundle, const char *cli_cert, const char *cli_key, const char *pskIdent, const char *psKey, bool insecure, const char **alpn_protos);
+int ssl_starttls_handshake(sslclient_context *ssl_client);
 void stop_ssl_socket(sslclient_context *ssl_client, const char *rootCABuff, const char *cli_cert, const char *cli_key);
 int data_to_read(sslclient_context *ssl_client);
 int send_ssl_data(sslclient_context *ssl_client, const uint8_t *data, size_t len);
 int get_ssl_receive(sslclient_context *ssl_client, uint8_t *data, int length);
+int send_net_data(sslclient_context *ssl_client, const uint8_t *data, size_t len);
+int get_net_receive(sslclient_context *ssl_client, uint8_t *data, int length);
+int peek_net_receive(sslclient_context *ssl_client, int timeout);
 bool verify_ssl_fingerprint(sslclient_context *ssl_client, const char* fp, const char* domain_name);
 bool verify_ssl_dn(sslclient_context *ssl_client, const char* domain_name);
 bool get_peer_fingerprint(sslclient_context *ssl_client, uint8_t sha256[32]);