From owner-freebsd-questions@FreeBSD.ORG Fri Sep 5 18:31:03 2008 Return-Path: Delivered-To: freebsd-questions@freebsd.org Received: from mx1.freebsd.org (mx1.freebsd.org [IPv6:2001:4f8:fff6::34]) by hub.freebsd.org (Postfix) with ESMTP id 6DA8F106566B for ; Fri, 5 Sep 2008 18:31:03 +0000 (UTC) (envelope-from ryallsd@gmail.com) Received: from wa-out-1112.google.com (wa-out-1112.google.com [209.85.146.182]) by mx1.freebsd.org (Postfix) with ESMTP id 2D2848FC17 for ; Fri, 5 Sep 2008 18:31:03 +0000 (UTC) (envelope-from ryallsd@gmail.com) Received: by wa-out-1112.google.com with SMTP id j4so377259wah.3 for ; Fri, 05 Sep 2008 11:31:02 -0700 (PDT) DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=gmail.com; s=gamma; h=domainkey-signature:received:received:message-id:date:from:to :subject:mime-version:content-type:content-transfer-encoding :content-disposition; bh=i9BTYuhabr3Kd6z2KLYRHs77Dgnx8DYxyPH90gyO2/4=; b=JiGvj83Ak1R+PTMF5gvZ5YLKJ4ez80RfSLNrsZCHPxJ48s3dMxA+TSDoz/QKdwTmk2 cA7qRtU603Dd4gYHWc4UL8vlxqM6BDBMwslUK/QiB7kV1Tazc9csOq8tPI3ZwH9xjRf/ OpDrXxtsJ436NjahDZkH5vDAIs8Jkjl1hR/bM= DomainKey-Signature: a=rsa-sha1; c=nofws; d=gmail.com; s=gamma; h=message-id:date:from:to:subject:mime-version:content-type :content-transfer-encoding:content-disposition; b=tm4ypwtmzYCDreb9uy7OCGU9H9VNPETxb2XshS7DYMzETIe0uFk/kNUx9IHHEhQTKG U62/J7PN1wRaBWDZ/6grCGkmKMfCYWwQ3wBfnEgKtLnsVXVjIeJyJL4bzOhQ0AGBdDoU UjWJCCr/4L73ZRHsrYWJdkh2cDJ6T5XgSNVRg= Received: by 10.114.205.1 with SMTP id c1mr10449192wag.56.1220639462574; Fri, 05 Sep 2008 11:31:02 -0700 (PDT) Received: by 10.114.160.14 with HTTP; Fri, 5 Sep 2008 11:31:02 -0700 (PDT) Message-ID: Date: Fri, 5 Sep 2008 11:31:02 -0700 From: "Derrick Ryalls" To: "FreeBSD Questions" MIME-Version: 1.0 Content-Type: text/plain; charset=ISO-8859-1 Content-Transfer-Encoding: 7bit Content-Disposition: inline Subject: sendmail not authenticating with smart host X-BeenThere: freebsd-questions@freebsd.org X-Mailman-Version: 2.1.5 Precedence: list List-Id: User questions List-Unsubscribe: , List-Archive: List-Post: List-Help: List-Subscribe: , X-List-Received-Date: Fri, 05 Sep 2008 18:31:03 -0000 Greetings, Due to port 25 restrictions, I am trying to get my brother's email server to authenticate out on port 587. I have sendmail talking via port 587, but it is not properly authenticating. To help narrow things down, I am having his machine route all mail to my machine with authentication. His machine is a running version 7: 7.0-RELEASE FreeBSD 7.0-RELEASE #0: Sun Feb 24 19:59:52 UTC 2008 Here are some relevant parts of the hostname.mc file: define(`SMART_HOST', `myserver.com') define(`confAUTH_MECHANISMS', `LOGIN PLAIN')dnl FEATURE(`authinfo',`hash /etc/mail/auth/client-info.db')dnl auth/client-info has this: AuthInfo:myserver.com "U:hisuser" "I:hisuser" "P:password" "M:PLAIN" And I have created client-info.db hash. I have copied the config file workflow from my server which uses smtp auth to talk to my ISP on port 587. On myserver.com, I do see that his machine connects to me, but I see this error in maillog: Relaying denied. Proper authentication required. When I was trying to go through his ISP, I got this error message in his error log: stat=Service unavailable. We share ISP (from different states though) and I am still able to send via my ISP. I even tried to directly copying my auth info for the ISP from my box to his (so he would be sending as me) and I got this same error. Have I missed a configuration setting somewhere?