diff -rup ssmtp-2.60/ssmtp.c ssmtp-2.60-starttls/ssmtp.c
--- ssmtp-2.60/ssmtp.c	2002-12-08 19:26:20.000000000 +0200
+++ ssmtp-2.60-starttls/ssmtp.c	2003-06-09 00:32:24.000000000 +0300
@@ -48,8 +48,12 @@ bool_t minus_t = False;
 bool_t minus_v = False;
 bool_t override_from = False;
 bool_t rewrite_domain = False;
+#ifdef HAVE_SSL
 bool_t use_tls = False;			/* Use SSL to transfer mail to HUB */
+bool_t use_starttls = False;    /* Use STARTTLS SMTP command to initiate TLS */
 bool_t use_cert = False;		/* Use a certificate to transfer SSL mail */
+bool_t tls_initialized = False;
+#endif
 
 #define ARPADATE_LENGTH 32		/* Current date in RFC format */
 char arpadate[ARPADATE_LENGTH];
@@ -878,11 +882,24 @@ bool_t read_config()
 					use_tls = False;
 				}
 
-				if(log_level > 0) { 
+				if(log_level > 0) {
 					log_event(LOG_INFO,
 						"Set UseTLS=\"%s\"\n", use_tls ? "True" : "False");
 				}
 			}
+			else if(strcasecmp(p, "UseSTARTTLS") == 0) {
+				if(strcasecmp(q, "YES") == 0) {
+					use_starttls = True;
+				}
+				else {
+					use_starttls = False;
+				}
+
+				if(log_level > 0) {
+					log_event(LOG_INFO,
+						"Set UseSTARTTLS=\"%s\"\n", use_starttls ? "True" : "False");
+				}
+			}
 			else if(strcasecmp(p, "UseTLSCert") == 0) {
 				if(strcasecmp(q, "YES") == 0) {
 					use_cert = True;
@@ -920,8 +937,11 @@ bool_t read_config()
 /*
 smtp_open() -- Open connection to a remote SMTP listener
 */
+void smtp_write(int fd, char *format, ...);
+int smtp_okay(int fd, char *response);
 int smtp_open(char *host, int port)
 {
+	char buf[(BUF_SZ + 1)];
 #ifdef INET6
 	struct addrinfo hints, *ai0, *ai;
 	char servname[NI_MAXSERV];
@@ -949,7 +969,7 @@ int smtp_open(char *host, int port)
 		return(-1);
 	}
 
-	if(use_cert == True) { 
+	if(use_cert == True) {
 		if(SSL_CTX_use_certificate_chain_file(ctx, tls_cert) <= 0) {
 			perror("Use certfile");
 			return(-1);
@@ -1028,11 +1048,24 @@ int smtp_open(char *host, int port)
 		return(-1);
 	}
 #endif
+	if(smtp_okay(s, buf) == False) {
+		log_event(LOG_ERR, "Invalid response SMTP server");
+		return(-1);
+	}
 
 #ifdef HAVE_SSL
 	if(use_tls == True) {
 		log_event(LOG_INFO, "Creating SSL connection to host");
 
+		if(use_starttls == True) {
+			smtp_write(s, "STARTTLS", hostname);
+			(void)alarm((unsigned) MEDWAIT);
+			if(smtp_okay(s, buf) == False) {
+				log_event(LOG_ERR, "STARTTLS failed: %s", buf);
+				return(-1);
+			}
+		}
+
 		ssl = SSL_new(ctx);
 		if(!ssl) {
 			log_event(LOG_ERR, "SSL not working");
@@ -1041,12 +1074,13 @@ int smtp_open(char *host, int port)
 		SSL_set_fd(ssl, s);
 
 		err = SSL_connect(ssl);
-		if(err < 0) { 
+		if(err < 0) {
 			perror("SSL_connect");
 			return(-1);
 		}
+		tls_initialized = True;
 
-		if(log_level > 0) { 
+		if(log_level > 0) {
 			log_event(LOG_INFO, "SSL connection using %s",
 				SSL_get_cipher(ssl));
 		}
@@ -1070,7 +1104,7 @@ fd_getc() -- Read a character from an fd
 ssize_t fd_getc(int fd, void *c)
 {
 #ifdef HAVE_SSL
-	if(use_tls == True) { 
+	if(use_tls == True && tls_initialized == True) {
 		return(SSL_read(ssl, c, 1));
 	}
 #endif
@@ -1134,10 +1168,10 @@ int smtp_okay(int fd, char *response)
 /*
 fd_puts() -- Write characters to fd
 */
-ssize_t fd_puts(int fd, const void *buf, size_t count) 
+ssize_t fd_puts(int fd, const void *buf, size_t count)
 {
 #ifdef HAVE_SSL
-	if(use_tls == True) { 
+	if(use_tls == True && tls_initialized == True) {
 		return(SSL_write(ssl, buf, count));
 	}
 #endif
@@ -1237,9 +1271,6 @@ int ssmtp(char *argv[])
 	if((sock = smtp_open(mailhost, port)) == -1) {
 		die("Cannot open %s:%d", mailhost, port);
 	}
-	else if(smtp_okay(sock, buf) == False) {
-		die("Invalid response SMTP server");
-	}
 
 	/* If user supplied username and password, then try ELHO */
 	if(auth_user) {
diff -rup ssmtp-2.60/ssmtp.conf ssmtp-2.60-starttls/ssmtp.conf
--- ssmtp-2.60/ssmtp.conf	2001-05-08 13:22:08.000000000 +0300
+++ ssmtp-2.60-starttls/ssmtp.conf	2003-06-09 00:35:01.000000000 +0300
@@ -30,6 +30,10 @@ hostname=_HOSTNAME_
 # Use SSL/TLS to send secure messages to server.
 #UseTLS=YES
 
+# Use STARTTLS SMTP command to initiate SSL, you should enable UseTLS too
+# for this option to work
+UseSTARTTLS=YES
+
 # Use SSL/TLS certificate to authenticate against smtp host.
 #UseTLSCert=YES