From mboxrd@z Thu Jan 1 00:00:00 1970 Path: news.gmane.org!not-for-mail From: Karl Fogel Newsgroups: gmane.emacs.devel Subject: Re: more on starttls, gnutls-cli and using tls for mail Date: Wed, 17 Aug 2011 10:28:15 -0400 Message-ID: <87pqk4i03k.fsf@kwarm.red-bean.com> References: <20039.8838.116211.694328@gargle.gargle.HOWL> <8762m0n5qi.fsf@red-bean.com> <87ipq0k0q0.fsf@red-bean.com> <87fwl4nqu8.fsf@gmail.com> <87ippzf7jx.fsf@gmail.com> Reply-To: Karl Fogel NNTP-Posting-Host: lo.gmane.org Mime-Version: 1.0 Content-Type: text/plain X-Trace: dough.gmane.org 1313591324 21535 80.91.229.12 (17 Aug 2011 14:28:44 GMT) X-Complaints-To: usenet@dough.gmane.org NNTP-Posting-Date: Wed, 17 Aug 2011 14:28:44 +0000 (UTC) Cc: Vijay Lakshminarayanan , Leo , emacs-devel@gnu.org To: Tim Cross Original-X-From: emacs-devel-bounces+ged-emacs-devel=m.gmane.org@gnu.org Wed Aug 17 16:28:37 2011 Return-path: Envelope-to: ged-emacs-devel@m.gmane.org Original-Received: from lists.gnu.org ([140.186.70.17]) by lo.gmane.org with esmtp (Exim 4.69) (envelope-from ) id 1Qth6j-0006W7-Jo for ged-emacs-devel@m.gmane.org; Wed, 17 Aug 2011 16:28:37 +0200 Original-Received: from localhost ([::1]:35744 helo=lists.gnu.org) by lists.gnu.org with esmtp (Exim 4.71) (envelope-from ) id 1Qth6i-0007aS-Vl for ged-emacs-devel@m.gmane.org; Wed, 17 Aug 2011 10:28:36 -0400 Original-Received: from eggs.gnu.org ([140.186.70.92]:52591) by lists.gnu.org with esmtp (Exim 4.71) (envelope-from ) id 1Qth6b-0007Zo-KY for emacs-devel@gnu.org; Wed, 17 Aug 2011 10:28:35 -0400 Original-Received: from Debian-exim by eggs.gnu.org with spam-scanned (Exim 4.71) (envelope-from ) id 1Qth6V-00071b-2U for emacs-devel@gnu.org; Wed, 17 Aug 2011 10:28:29 -0400 Original-Received: from mail-vx0-f169.google.com ([209.85.220.169]:47987) by eggs.gnu.org with esmtp (Exim 4.71) (envelope-from ) id 1Qth6U-00071S-UE for emacs-devel@gnu.org; Wed, 17 Aug 2011 10:28:23 -0400 Original-Received: by vxj3 with SMTP id 3so1055793vxj.0 for ; Wed, 17 Aug 2011 07:28:21 -0700 (PDT) DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=gmail.com; s=gamma; h=sender:from:to:cc:subject:references:reply-to:date:in-reply-to :message-id:user-agent:mime-version:content-type; bh=PEG933pbQnvGUvZfS1WacKEa5kOmELnOTpgzeBTBkxI=; b=rvD0ipnCOtxTr1MK2DBV9Sf+MZN8+7Vhgo9kPKccRRcs4Sy4pmZjZylsUilgNpMOoX R92fjX/N0InM+NoBQjQBfdIvaSJYZYzE4d+Nw7s58F2dAJYJjECFfmbfohge4tbLyuJh kWPcbSkacLk5349tM5+Xu47PqxXxveOJaww28= Original-Received: by 10.52.91.142 with SMTP id ce14mr1000007vdb.167.1313591300409; Wed, 17 Aug 2011 07:28:20 -0700 (PDT) Original-Received: from kwarm.red-bean.com (topp148-office-nyc.openplans.org [67.221.177.15]) by mx.google.com with ESMTPS id j8sm1072669vdv.47.2011.08.17.07.28.17 (version=TLSv1/SSLv3 cipher=OTHER); Wed, 17 Aug 2011 07:28:17 -0700 (PDT) In-Reply-To: (Tim Cross's message of "Wed, 17 Aug 2011 11:54:01 +1000") User-Agent: Gnus/5.13 (Gnus v5.13) Emacs/24.0.50 (gnu/linux) X-detected-operating-system: by eggs.gnu.org: GNU/Linux 2.6 (newer, 2) X-Received-From: 209.85.220.169 X-BeenThere: emacs-devel@gnu.org X-Mailman-Version: 2.1.14 Precedence: list List-Id: "Emacs development discussions." List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , Errors-To: emacs-devel-bounces+ged-emacs-devel=m.gmane.org@gnu.org Original-Sender: emacs-devel-bounces+ged-emacs-devel=m.gmane.org@gnu.org Xref: news.gmane.org gmane.emacs.devel:143370 Archived-At: Tim Cross writes: >OK, thanks Jijay. So, it would seem the use case is possibly something >specific google has done to detect possible abuse of an email account. >I've not run into this myself, but at least this gives one possible >data point on why this additional complexity may be required. There's another issue too: Although "smtp.gmail.com" is the One True Server for sending mails through Google [1], the account you log in with there could be a regular Google/Gmail account (call this type "A") or it could be a Google Apps For Your Domain (type "B") account. These are rather different beasts. While you could set up your "A" account such that it's able to send mail with a From address that is really of type "B", I had some experiences -- clean reproduction recipes are hard to create, unfortunately -- that indicated there could be authn problems or being-blocked-as-spam problems if I sent from type "A" repeatedly with a From address of type "B". But these problems go away if I authenticate to smtp.gmail.com as user "B" whenever sending mail with an address of type "B". Again, in practice it's impossible to get definitive answers to what the rules are. Running experiments is very time consuming, it's hard to isolate variables, and Google doesn't have the staff to answer in-depth technical questions (though random members of the public sometimes do -- see [2]). Essentially, running one's own email server has become too hard nowadays, but if one uses an email server hosted by an organization large enough to deal competently with the running an email server in the modern era, then by definition that organization will be too large to answer individual questions. The problem is systemic; I'm not blaming Google -- I'm glad they offer the smtp.gmail.com service. So I have to get Emacs to switch sender authn creds on an email-by-email basis. Recent smtpmail.el changes have made this harder, not easier. -Karl [1] The reason I send mail through Google is because if I use my own server, it can be difficult to avoid the server being blacklisted even when that server is not the origin of any spam. See http://www.rants.org/2010/05/26/email-blacklisting-considered-harmful/ [2] http://www.google.com/support/forum/p/gmail/thread?tid=45781946ea84651e