[UFO Chicago] How Do You Configure Sendmail To Relay Outgoing Mail Thru An Encrypted Connection?

[Jay F Shachter]

Here is a verbatim transcript of an hourlong chat I had with my ATT
technical service representative.  I hope it will be more amusing for
you to read it than it was for me to participate in it.  And if you
can answer the question that Zachary could not even comprehend, I
shall be much obliged.



Thank you for choosing AT&T. A representative will be with you shortly.

You are now chatting with 'ZACHARY'

Jay Shachter: When your mail relay host at smtp.att.yahoo.com

ZACHARY: Thank you for contacting AT&T . My name is Zachary.

Jay Shachter: decided that it would only accept encrypted connections o=
n

Jay Shachter: port 587 (which is, parenthetically, highly annoying),

Jay Shachter: you provided us with the postfix configuration for settin=
g

Jay Shachter: that up. Now I want to start using sendmail rather than

Jay Shachter: postfix as my MTA, and I don't see how to configure

Jay Shachter: sendmail to do the same thing (e.g., I can set the Ds

Jay Shachter: macro to define the "smart host", but how do I define the

Jay Shachter: TCP port, since it isn't 25? and how do I tell sendmail

Jay Shachter: to encrypt?)

Jay Shachter: Please send me the appropriate sendmail configuration

Jay Shachter: directives. You can e-mail them to jay at m5.chicago.il.us

Jay Shachter: if that's easier than typing them into a chat window. o

ZACHARY: I understand your concern and will be glad to assist you.

ZACHARY: Before that I need to locate your account details.

ZACHARY: I see that I'm chatting with Jay Shachter and you have provide=
d 7737613784 as the dsl number associated with your account, am I corre=
ct ?

Jay Shachter: Please don't tell me useless things like "I understand yo=
ur concern and will be glad to assist you". That just annoys people and=
 wastes their time. What account details do you need that I didn't alre=
ady give you?

ZACHARY: Yes.

Jay Shachter: Yes, as I already indicated, my number is +1 773 7613784.

ZACHARY: I want to confirm that the information you have entered, is it=
 correct.

ZACHARY: Thank you.

ZACHARY: Jay, let me know your e-mail address which you want to configu=
re or you are using in e-mail client.

ZACHARY: I am waiting for your response.

Jay Shachter: I have no idea what you just asked me. What do you mean, =
"let me know your e-mail address which you want to configure?" As I tho=
ught I indicated, I have an MTA that needs to go thru your relay host, =
smtp.att.yahoo.com, to send outgoing mail, since direct connections fro=
m a dynamic IP address are rarely accepted these days. Your relay host,=
 however, much to everyone's annoyance, decided a few years ago that it=
 would no longer accept unencrypted connections on port 25, it would on=
ly accept encrypted connections on port 587. I need to have sendmail co=
nfiguration directives that will get sendmail to relay all outgoing mai=
l thru port 587 on smtp.att.yahoo.com. I'm already doing it on postfix,=
 but I'm switching over to sendmail. o

ZACHARY: AT&T ports have changed. Instead of smtp.att.yahoo.com you nee=
d to use outbound.att.net and port number 465

ZACHARY: The incoming server is inbound.att.net and port number 995.

Jay Shachter: Well that's interesting, since I've been using smtp.att.y=
ahoo.com for years and it works, it most recently worked just a few min=
utes ago. In fact, it gave me grief because I had to waste about half a=
n hour "setting up a new e-mail account" because I wanted to use a diff=
erent "From" address that I hadn't used before.

Jay Shachter: Anyway, I can use outbound.att.net and port number 465 if=
 you like, but the question remains, I still need sendmail configuratio=
n directives. By the way, when I connect to outbound.att.net:465, is th=
at encrypted or unencrypted? o

ZACHARY: It is encrypted.

Jay Shachter: Then I still need to know how to configure sendmail to re=
lay outgoing mail thru an encrypted connection on a nonstandard port. o

ZACHARY: Thank you for waiting. I'll be with you in just a moment.

ZACHARY: Port 465 is non standard port.

ZACHARY: Port 25 and 587 are the Standard ports.

ZACHARY: 587 works on Unencryption.

ZACHARY: Jay, is there anything else may I assist you with today ?

Jay Shachter: What do you mean, "anything else"? You haven't assisted m=
e with anything yet. As I said, I need to know how to configure sendmai=
l to relay outgoing mail thru an encrypted connection on a non-standard=
 port.

Jay Shachter: By the way, that statement you uttered a moment ago, "587=
 works on Unencryption", is rubbish, at least with respect to smtp.att.=
yahoo.com. I have postfix currently set up using port 587 with encrypte=
d connections to smtp.att.yahoo.com. I have logs of the SMTP traffic, a=
nd my MTA is definitely sending a "STARTTLS" message to your MTA.

ZACHARY: You need to use AT&T outbound server to relay the mails.

ZACHARY: We need to use 465 port number for the outgoing server instead=
 of 587.

Jay Shachter: Yes, I know that. How do I configure sendmail to relay ou=
tgoing mail to your relay host on port 465?

Jay Shachter: And how do I configure sendmail to encrypt the conversati=
on?

ZACHARY: Do you remember your AT&T primary e-mail address and password.

Jay Shachter: Yes, I do know that.

ZACHARY: Do you remember your AT&T primary e-mail address and password?

ZACHARY: Let me know the e-mail client you are using to send mails.

Jay Shachter: My MTA is sendmail. Actually, it is currently postfix, bu=
t I'm switching from postfix to sendmail. You're talking as if I have b=
een unclear about this, whereas in fact I have been quite clear about i=
t, and have now repeated that statement at least 4 times. o

ZACHARY: Jay, we need to use outbound.att.net as the outbound server to=
 send mails.

ZACHARY: The server which you are using for sending the mails is the ol=
d server.

Jay Shachter: Yes, I know that. You really don't have to say that more =
than 3 times. How do I configure sendmail to relay its outbound traffic=
 to your relay host, using port 465, and on an encrypted connection? I =
know that I am repeating myself, but you keep on failing to answer the =
question. o

ZACHARY: For that I need to know the e-mail client you are using so tha=
t I will provide you steps.

Jay Shachter: My MTA, as I have said more times than I can readily coun=
t, is sendmail. Are you asking for my MUA? That's utterly irrelevant. o

ZACHARY: I'm sorry for the delay. I'll be right with you.

ZACHARY: Jay, in order to relay your account , we need to first log in =
to your email account through webmail using Internet Explorer or Firefo=
x.

ZACHARY: Then we need to add the third party email accounts in the add =
accounts settings and once the changes have been saved in the webmail t=
hen it will be working fine.

ZACHARY: Let me know once you are logged in to your email through webma=
il .

Jay Shachter: I have no idea what you are talking about. What "third pa=
rty email accounts"? And what has that to do with telling my MTA to use=
 encryption and a nonstandard port? Any filtering vis-a-vis "third part=
y accounts" would only occur after the MAIL FROM: line, which presuppos=
es a TCP connection. o

ZACHARY: I will be right with you.

ZACHARY: Jay, the third party email account that you mentioned "  jay at m=
5.chicago.il.us "

ZACHARY: We need to add up this account in your email through webmail a=
nd then once it will be added it will send the verification email to th=
is email in order to send the emails .

Jay Shachter: I did that about 10 years ago. That has nothing to do wit=
h my question.

ZACHARY: Okay

ZACHARY: Jay,  I understand your point.

Jay Shachter: I have been using jay at m5.chicago.il.us for years. I curre=
ntly send outbound mail from that address using postfix as my MTA. I wa=
nt to know how to do the same thing using sendmail as my MTA.

ZACHARY: As a valued member of the AT&T family, we provide additional a=
ssistance with your computer software, hardware/peripherals, or network=
ing problems on up to 4 PC~s. This also includes other devices like: Xb=
ox, Kindle, WII etc. You can subscribe to this service for a nominal fe=
e of 50 cents/day ($15 per month).   Would you be interested in learnin=
g more about ConnectTech and how it can help you?

ZACHARY: jay, we have a separate team that takes care of this email thi=
rd party related issues .

ZACHARY: And I want your issue to be resolved quickly.

Jay Shachter: I have no interest in ConnectTech. I don't even know what=
 that is. I have never heard of it before, and I don't care to learn ab=
out it now. Here is an excerpt from my postfix configuration file; I ne=
ed to translate it into the corresponding sendmail configuration (mutat=
is mutandis for the change in relay host and port number): relayhost =
=3D [smtp.att.yahoo.com]:587 mailbox_command =3D mailbox_transport =3D =
strict_8bitmime =3D no disable_mime_output_conversion =3D no smtpd_send=
er_restrictions =3D hash:/etc/postfix/access smtpd_client_restrictions =
=3D smtpd_helo_required =3D no smtpd_helo_restrictions =3D strict_rfc82=
1_envelopes =3D no smtpd_recipient_restrictions =3D permit_mynetworks,r=
eject_unauth_destination smtp_sasl_auth_enable =3D yes smtpd_sasl_auth_=
enable =3D no broken_sasl_auth_clients =3D yes smtp_sasl_password_maps =
=3D hash:/etc/postfix/sasl_passwd smtp_sasl_mechanism_filter =3D plain,=
 login smtp_sasl_security_options =3D noanonymous smtp_sasl_type =3D cy=
rus smtpd_use_tls =3D no smtp_use_tls =3D no smtp_tls_security_level =
=3D may

Jay Shachter: (there were newline characters in the pasted text, your c=
hat window software elided them)

ZACHARY: Jay, the relay hosts should be outbound.att.net as for the AT&=
T settings for the sending mails .

ZACHARY: I understand that you received an error when using your [Send =
mail relay ].  However, as the error persists, I can refer you to our C=
onnectTech department for further troubleshooting in checking your clie=
nt mail configuration.

Jay Shachter: Yes, I know. As I just wrote a moment ago, "mutatis mutan=
dis for the change in relay host and port number". And I did not receiv=
e an error. My postfix MTA works perfectly fine. I just need to know ho=
w to get sendmail to do the same thing.

ZACHARY: yes, for this information I am advising you to please contact =
our connectech team and they will provide you the complete information =
about the same.

ZACHARY: AT&T Support Plus is a monthly subscription service that provi=
des with virtually unlimited 24/7 help over the phone and Internet 24 h=
ours a day, 7 days a week, for computer software, hardware/peripheral, =
or networking problems on up to four PCs in their home, all for a low f=
ee of $15 per month.

ZACHARY: Since, you are still experiencing the issue with the send mail=
 , so they will resolve the issue and if they are unable to resolve the=
 issue then there will be no charges and your money will be refunded.

ZACHARY: The Connectech team is a one stop shop. It will save the valua=
ble time and avoid contacting multiple customer service locations or su=
rfing the Internet for hard to find answers when a problem arises. You =
can rely on AT&T Support Plus to cover a wide variety services/support =
to address your technical needs.

ZACHARY: It also helps with operating system problems or conflicts.

ZACHARY: Configure, troubleshoot, and set up e-mail accounts.

ZACHARY: Set-up and configuration of networked devices such as gaming d=
evices, wireless printers, webcams, and digital cameras.

ZACHARY: Assistance with removal of virus/malware/adware.

Jay Shachter: I didn't have to pay anyone $15 a month when your relay h=
ost decided it would henceforth only accept encrypted connections. You =
just directed me to a place where I could find the appropriate postfix =
configuration directives. All I need now is the same information, but f=
or sendmail.

ZACHARY: Yes, I would advise you to please contact the connectech team =
and they will provide you the complete information about the same , if =
you want I can provide you the direct contact details of the concerned =
department or if you want I can add the service in your account .

Jay Shachter: You have been utterly worthless. In fact, you have been l=
ess than worthless, because you took up an hour of time (it has literal=
ly been more than an hour, I am amazed to see), instead of telling me a=
n hour ago that you were utterly worthless and I would be wasting my ti=
me expecting you to help me with my problem, or even to understand it. =
o+o

ZACHARY: Jay, I have provided you the email cilient settings for the ou=
tbound and inbound email settings and I am providing you the help artic=
le for further email settings .

ZACHARY: http://www.att.com/esupport/article.jsp?sid=3DKB401568

ZACHARY: I understand your frustration , however they can provide you t=
he support to all the issues related to the Sendmail ( relay ) for the =
postfix and all the other issues .

ZACHARY: Jay, is there anything else may I assist you with today ?

Jay Shachter: Asking me if there is "anything else" that you can help m=
e with is highly inappropriate, because the word "else" implies that yo=
u have already helped me with something, which you have not done. It is=
 like asking Alice if she wants more tea. I had only that one question,=
 and you did not help me with it.


=09=09Jay F. Shachter
=09=096424 N Whipple St
=09=09Chicago IL  60645-4111
=09=09=09(1-773)7613784   landline
=09=09=09(1-410)9964737   GoogleVoice
=09=09=09jay at m5.chicago.il.us
=09=09=09http://m5.chicago.il.us

=09=09"This was untrue.  I am not even faintly like a rose."