Package: swaks
Version: 20240103.0-1
Severity: normal

eg. connecting to an SSMTPA on port 465:

   swaks -a -tlsc --server submission.example.com --to mich...@example.com

Successfully connects on port 465, negotiates SSL, but then bombs out
complaining that STARTTLS is not advertised (names changed to protect the
innocent):

   === Trying submission.example.com:465...
   === Connected to submission.example.com.
   === TLS started with cipher TLSv1.3:TLS_AES_256_GCM_SHA384:256
   === TLS client certificate not requested and not sent
   === TLS no client certificate set
   === TLS peer[0]   subject=[/CN=*.example.com]
   ===               commonName=[*.example.com], 
subjectAltName=[DNS:*.example.com, DNS:example.com] 
notAfter=[2024-11-12T02:14:49Z]
   === TLS peer[1]   subject=[/C=US/O=Let's Encrypt/CN=R10]
   ===               commonName=[R10], subjectAltName=[] 
notAfter=[2027-03-12T23:59:59Z]
   === TLS peer certificate passed CA verification, passed host verification 
(using host submission.example.com to verify)
   <~  220 mailfish.example.com ESMTP
    ~> EHLO joyola
   <~  250-mailfish.example.com
   <~  250-PIPELINING
   <~  250-SIZE 50720000
   <~  250-ETRN
   <~  250-AUTH LOGIN PLAIN
   <~  250-AUTH=LOGIN PLAIN
   <~  250-ENHANCEDSTATUSCODES
   <~  250-8BITMIME
   <~  250-DSN
   <~  250-SMTPUTF8
   <~  250 CHUNKING
   *** Host did not advertise STARTTLS
    ~> QUIT
   <~  221 2.0.0 Bye
   === Connection closed with remote host.

I think --tls-on-connect should imply something similar to --tls-optional (I
would argue that advertising STARTTLS here would actually be a configuration
error).

Versions of packages swaks depends on:
ii  perl  5.38.2-5

Versions of packages swaks recommends:
ii  libio-socket-inet6-perl  2.73-1
pn  libnet-dns-perl          <none>
ii  libnet-ssleay-perl       1.94-1+b1

Versions of packages swaks suggests:
pn  libauthen-ntlm-perl  <none>
ii  libauthen-sasl-perl  2.1600-3
ii  perl-doc             5.38.2-5

-- debconf-show failed

-MD

-- 
-----------------------------------------------------------------------------
Michael Deegan               Hugaholic              https://www.deegan.id.au/
------------------------  Jung, zr jbeel?  ----------------------------------

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