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

Brian Sobolak brian at planetshwoop.com
Sun Jan 12 18:06:38 PST 2014

Clearly you are talking to Liza, not Zachary.

You could conceivably have used emacs to get a similar result.  It would have at least had the line formatting correct.

Brian Sobolak 
brian at planetshwoop.com

> On Jan 8, 2014, at 12:18 AM, "Jay F Shachter" <jay at m5.chicago.il.us> wrote:
> 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?
> 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: 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."
> _______________________________________________
> UFO Chicago -- Users of Free Operating Systems
> Free Software Rules -- Proprietary Drools!
> http://ufo.chicago.il.us/cgi-bin/mailman/listinfo/ufo

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