diff --git a/collects/net/doc.txt b/collects/net/doc.txt
index a021d10cb8..0c794374eb 100644
--- a/collects/net/doc.txt
+++ b/collects/net/doc.txt
@@ -497,7 +497,12 @@ EXCEPTIONS -----------------------------------------------------------
 PROCEDURES -----------------------------------------------------------
 
 > (smtp-send-message server-string from-string to-list-of-strings header
-                     message-list-of-strings/bytes [port]) -> void
+                     message-list-of-strings/bytes 
+		     [#:port-no k] 
+		     [#:auth-user user-string-or-#f]
+		     [#:auth-passwd pw-string-or-#f]
+		     [#:tcp-connect proc]
+		     [port-no]) -> void
 
   The first argument is the IP address of the SMTP server. The
   `from-string' argument specifies the mail address of the sender, and
@@ -509,11 +514,24 @@ PROCEDURES -----------------------------------------------------------
   message, where each string or byte string in the list corresponds to
   a single line of message text; no string in
   `message-list-of-strings' should contain a carriage return or
-  newline characters. The optional `port' argument specifies the IP
-  port to use in contacting the SMTP server; the default is 25.
+  newline characters.
 
-  See the head package for utilities that construct a message headers
-  and validate mail address strings.
+  The optional `port-no' argument --- which can be specified either
+  with the #:port-no keyword or, for backward compatibility, as an
+  extra argument after keywords --- specifies the IP port to use in
+  contacting the SMTP server; the default is 25.
+
+  The optional #:auth-user and #:auth-passwd keyword argument supply a
+  username and password for authenticated SMTP (using the AUTH PLAIN
+  protocol).
+
+  The optional #:tcp-connect keyword argument supplies a connection
+  procedure to be used in place of `tcp-connect'. For example, use
+  `ssl-connect' from `(lib "mzssl.ss" "openssl")' to connect to the
+  server via SSL.
+
+  See the "head.ss" library for utilities that construct a message
+  headers and validate mail address strings.
 
 > (smtp-sending-end-of-message [proc])
 
diff --git a/collects/net/smtp-unit.ss b/collects/net/smtp-unit.ss
index 980ac248db..5b34a5d214 100644
--- a/collects/net/smtp-unit.ss
+++ b/collects/net/smtp-unit.ss
@@ -1,6 +1,8 @@
 
 (module smtp-unit mzscheme
-  (require (lib "unitsig.ss"))
+  (require (lib "unitsig.ss")
+	   (lib "kw.ss")
+	   "base64.ss")
 
   (require "smtp-sig.ss")
 
@@ -60,7 +62,8 @@
 			    (raise-type-error 'smtp-sending-end-of-message "thunk" f))
 			  f)))
       
-      (define (smtp-send-message* r w sender recipients header message-lines)
+      (define (smtp-send-message* r w sender recipients header message-lines
+				  auth-user auth-passwd)
 	    (with-handlers ([void (lambda (x)
 				    (close-input-port r)
 				    (close-output-port w)
@@ -70,6 +73,15 @@
 	      (fprintf w "EHLO ~a~a" ID crlf)
 	      (check-reply r 250 w)
 	      
+	      (when auth-user
+		(log "auth~n")
+		(fprintf w "AUTH PLAIN ~a"
+			 ;; Encoding adds CRLF
+			 (base64-encode
+			  (string->bytes/latin-1
+			   (format "~a\0~a\0~a" auth-user auth-user auth-passwd))))
+		(check-reply r 235 w))
+
 	      (log "from~n")
 	      (fprintf w "MAIL FROM:<~a>~a" sender crlf)
 	      (check-reply r 250 w)
@@ -107,13 +119,18 @@
 	      (close-input-port r)))
       
       (define smtp-send-message
-	(case-lambda
-	 [(server sender recipients header message-lines)
-	  (smtp-send-message server sender recipients header message-lines 25)]
-	 [(server sender recipients header message-lines pos)
+	(lambda/kw (server sender recipients header message-lines 
+			   #:key 
+			   [port-no 25]
+			   [auth-user #f]
+			   [auth-passwd #f]
+			   [tcp-connect tcp-connect]
+			   #:body
+			   (#:optional [opt-port-no port-no]))
 	  (when (null? recipients)
 	    (error 'send-smtp-message "no receivers"))
 	  (let-values ([(r w) (if debug-via-stdio?
 				  (values (current-input-port) (current-output-port))
-				  (tcp-connect server pos))])
-	    (smtp-send-message* r w sender recipients header message-lines))])))))
\ No newline at end of file
+				  (tcp-connect server opt-port-no))])
+	    (smtp-send-message* r w sender recipients header message-lines
+				auth-user auth-passwd)))))))
diff --git a/collects/sirmail/doc.txt b/collects/sirmail/doc.txt
index 8e7482cf28..e455799c93 100644
--- a/collects/sirmail/doc.txt
+++ b/collects/sirmail/doc.txt
@@ -54,11 +54,11 @@ Sending panel:
 
   - Mail From: The user's email address.
 
-  - SMTP Server: The SMTP server's host name (outgoing mail).  Use a
-    ":<portno>" suffix on the host name to connect to port
-    <portno>. Supply multiple SMTP hosts by separating the addresses
-    with a comma; the "File" menu of mail-sending frame will let you
-    choose a specific server.
+  - SMTP Server: The SMTP server's host name (outgoing mail). General
+    syntax: [<type>:][<user>@]<host>[:<portno>] where <type> is "tcp"
+    (the default) or "ssl". Supply multiple SMTP hosts by separating
+    the addresses with a comma; the "File" menu of mail-sending frame
+    will let you choose a specific server.
 
   - Default To Domain: If a destination address that isn't declared as
     an alias doesn't include a domain name, SirMail automatically
diff --git a/collects/sirmail/optionr.ss b/collects/sirmail/optionr.ss
index 15c77d10a0..b253b74504 100644
--- a/collects/sirmail/optionr.ss
+++ b/collects/sirmail/optionr.ss
@@ -29,6 +29,19 @@
 	      (values (cadr m) (string->number (caddr m)))
 	      (values s default-port))))
 
+      (define (parse-server-name+user+type s default-port)
+	(let ([m (regexp-match #rx"^(ssl|tcp):.*:.*" s)])
+	  (let-values ([(ssl? s) (if m
+				     (values (string=? "ssl" (substring s 0 3))
+					     (substring s 4))
+				     (values #f s))])
+	    (let ([m (regexp-match #rx"^(.*)@(.*)$" s)])
+	      (let-values ([(user s) (if m
+					 (values (cadr m) (caddr m))
+					 (values #f s))])
+		(let-values ([(server port) (parse-server-name s default-port)])
+		  (values ssl? user server port)))))))
+
       ;; ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
       ;;  Preferences                                            ;;
       ;; ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
diff --git a/collects/sirmail/pref.ss b/collects/sirmail/pref.ss
index df7c3bae51..ce746b09c9 100644
--- a/collects/sirmail/pref.ss
+++ b/collects/sirmail/pref.ss
@@ -316,9 +316,21 @@
 	       (<= 1 (string->number (caddr m)) 65535)
 	       (is-host-address? (cadr m))))))
 
-  (define (is-host-address+port-list? s)
+  (define (is-host-address+port+user? s)
+    (or (is-host-address+port? s)
+	(let ([m (regexp-match "^(?:[-+a-zA-Z0-9_.]+)@(.*)$" s)])
+	  (and m
+	       (is-host-address+port? (cadr m))))))
+
+  (define (is-host-address+port+user+type? s)
+    (or (is-host-address+port+user? s)
+	(let ([m (regexp-match "^(?:ssl|tcp):(.*)$" s)])
+	  (and m
+	       (is-host-address+port+user? (cadr m))))))
+
+  (define (is-host-address+port+user+type-list? s)
     (let ([l (regexp-split ", *" s)])
-      (andmap is-host-address+port? l)))
+      (andmap is-host-address+port+user+type? l)))
 
   (define (check-address ok? who tl s port-ok? multi?)
     (or (ok? s)
@@ -352,8 +364,8 @@
     (check-address is-host-address? who tl s #f #f))
   (define (check-host-address/port who tl s)
     (check-address is-host-address+port? who tl s #t #f))
-  (define (check-host-address/port/multi who tl s)
-    (check-address is-host-address+port-list? who tl s #t #t))
+  (define (check-host-address/port/user/type/multi who tl s)
+    (check-address is-host-address+port+user+type-list? who tl s #t #t))
 
   ;; check-biff-delay : (union #f string) (union #f parent) string -> boolean
   ;; checks to see if the string in the biff delay field makes
@@ -472,7 +484,8 @@
     (let ([p (instantiate vertical-panel% (parent))])
       
       (make-text-field "Mail From" p 20 'sirmail:mail-from #f check-user-address (lambda (x) x) (lambda (x) x))
-      (make-text-field "SMTP Server" p 20 'sirmail:smtp-server #f check-host-address/port/multi (lambda (x) x) (lambda (x) x))
+      (make-text-field "SMTP Server" p 20 'sirmail:smtp-server #f check-host-address/port/user/type/multi 
+		       (lambda (x) x) (lambda (x) x))
 
       (make-file/directory-button #t #f p
 				  'sirmail:sent-directory
diff --git a/collects/sirmail/readr.ss b/collects/sirmail/readr.ss
index 365e60082a..d17ac419e3 100644
--- a/collects/sirmail/readr.ss
+++ b/collects/sirmail/readr.ss
@@ -255,12 +255,8 @@
                             ;; New connection
                             (begin
 			      (let ([pw (or (get-PASSWORD)
-					    (let ([p (get-text-from-user "Password" 
-									 (format "Password for ~a:" (USERNAME))
-									 main-frame
-									 ""
-									 '(password))])
-					      (unless p (raise-user-error 'connect "connection cancelled"))
+					    (let ([p (get-pw-from-user (USERNAME) main-frame)])
+					      (unless p (raise-user-error 'connect "connection canceled"))
 					      p))])
 				(let*-values ([(imap count new) (let-values ([(server port-no)
 									      (parse-server-name (IMAP-SERVER)
diff --git a/collects/sirmail/sendr.ss b/collects/sirmail/sendr.ss
index 490b99f01a..d03a70bd15 100644
--- a/collects/sirmail/sendr.ss
+++ b/collects/sirmail/sendr.ss
@@ -11,7 +11,8 @@
   (require (lib "list.ss")
 	   (lib "file.ss")
 	   (lib "string.ss")
-	   (lib "process.ss"))
+	   (lib "process.ss")
+	   (lib "mzssl.ss" "openssl"))
 
   (require "sirmails.ss"
 	   "pref.ss"
@@ -25,6 +26,8 @@
 
   (require (lib "hierlist-sig.ss" "hierlist"))
 
+  (define smtp-passwords (make-hash-table 'equal))
+
   (provide send@)
   (define send@
     (unit/sig sirmail:send^
@@ -410,12 +413,20 @@
             w))
         
         (define (send-msg)
-          (define-values (smtp-server-to-use smtp-port-to-use)
-            (parse-server-name (SMTP-SERVER) 25))
+          (define-values (smtp-ssl? smtp-auth-user smtp-server-to-use smtp-port-to-use)
+            (parse-server-name+user+type (SMTP-SERVER) 25))
+	  (define smtp-auth-passwd (and smtp-auth-user
+					(or (hash-table-get smtp-passwords (cons smtp-auth-user smtp-server-to-use)
+							    (lambda () #f))
+					    (let ([p (get-pw-from-user smtp-auth-user mailer-frame)])
+					      (unless p (raise-user-error 'send "send canceled"))
+					      p))))
           (send-message
            (send message-editor get-text)
+	   smtp-ssl?
            smtp-server-to-use
            smtp-port-to-use
+	   smtp-auth-user smtp-auth-passwd
            (map (lambda (i) (send i user-data)) 
                 (send enclosure-list get-items))
            enable
@@ -433,7 +444,10 @@
                    (if f
                        (send message-editor save-file f 'text)
                        (loop))))))
-           message-count))
+           message-count)
+	  (when smtp-auth-passwd
+	    (hash-table-put! smtp-passwords (cons smtp-auth-user smtp-server-to-use) 
+			     smtp-auth-passwd)))
         
         ;; enq-msg : -> void
         ;; enqueues a message for a later send
@@ -592,7 +606,7 @@
 				      (new-mailer p "" "" "" "" "" 
 						  (map (lambda (i) (send i user-data)) 
 						       (send enclosure-list get-items))
-						  0)
+						  message-count)
 				      (semaphore-post s)))
 				   (semaphore-wait s)))]
 		     [shortcut #\=])
@@ -711,8 +725,9 @@
       ;; ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
 
       (define (send-message message-str
+			    ssl?
                             smtp-server
-                            smtp-port
+                            smtp-port auth-user auth-pw
                             enclosures
                             enable 
                             status-message-starting
@@ -793,7 +808,10 @@
                                               tos
                                               new-header
                                               body-lines
-                                              smtp-port))))
+                                              #:port-no smtp-port
+					      #:tcp-connect (if ssl? ssl-connect tcp-connect)
+					      #:auth-user auth-user
+					      #:auth-passwd auth-pw))))
                        save-before-killing))
                   (status-done))
                 (message-box
diff --git a/collects/sirmail/sirmails.ss b/collects/sirmail/sirmails.ss
index 81d8b596ea..ef78a58fd0 100644
--- a/collects/sirmail/sirmails.ss
+++ b/collects/sirmail/sirmails.ss
@@ -37,6 +37,8 @@
 
      confirm-box
 
+     get-pw-from-user
+
      generalize-encoding
      parse-encoded
      encode-for-header))
@@ -76,7 +78,8 @@
      
      USE-EXTERNAL-COMPOSER?
 
-     parse-server-name))
+     parse-server-name
+     parse-server-name+user+type))
 
   (provide sirmail:read^)
   (define-signature sirmail:read^
diff --git a/collects/sirmail/utilr.ss b/collects/sirmail/utilr.ss
index fc1f5c900f..531d9c9cbf 100644
--- a/collects/sirmail/utilr.ss
+++ b/collects/sirmail/utilr.ss
@@ -230,6 +230,15 @@
 	      'yes
 	      'no)))
 
+      ;; ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
+
+      (define (get-pw-from-user username parent)
+	(get-text-from-user "Password" 
+			    (format "Password for ~a:" username)
+			    parent
+			    ""
+			    '(password)))
+
       ;; ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
       ;;  Decoding `from' names                                  ;;
       ;; ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;