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Alpine email client: send mail from a different server via ssh

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I have suffered from important emails not being received, while I do not receive a bounce message. I wonder whether one factor in this problem is that my laptop, which sometimes has a dynamically-allocated IP address, appears to be the sender if Alpine talks directly to some (major) SMTP server. My email may get less respect if it comes from a laptop. So can I change the smtp-server setting in Alpine to use sendmail on a different (fixed IP) machine, rather than the sendmail on my laptop? I have passwordless ssh keys set up already my remote (tunnel) server. What string can I put to tell Alpine to tunnel elsewhere for sendmail? Right now for smtp-server I am just specifying a remote SMTP server's IP name and port number, with the Alpine-format tls or ssl and user= string, but I want instead to pass these via ssh to the mailer on another GNU/Linux machine. (I'm actually using the smtp-rules setting rather than the default smtp-server setting.) A bit more detail (to explain my motivation): Here is the bottom part of the header of a very important email message which was never received (major damage ensued) and which generated no bounce: Received: from Mylaptop-high (192-0-111-216.cpe.teksavvy.com [192.0.111.216]) (authenticated bits=0) (User authenticated as meuser@ALUM.MIT.EDU) by outgoing-alum.mit.edu (8.14.7/8.12.4) with ESMTP id 03F39FMc032212 (version=TLSv1/SSLv3 cipher=DHE-RSA-AES256-GCM-SHA384 bits=256 verify=NOT); Tue, 14 Apr 2020 23:09:16 -0400 Date: Tue, 14 Apr 2020 23:09:15 -0400 (EDT) From: C P meuser To: Important recipient Subject: life or death emergency Message-ID: User-Agent: Alpine 2.21 (DEB 202 2017-01-01) Other servers will look at this and find that it originated on my laptop, which was currently at home with my ISP's IP (teksavvy). Not optimally, I sent it via MIT's smtp server rather than McGill's. However, MIT authenticated me and successfully delivered it back to me through a bcc address. But something stopped it getting to the Recipient. That, presumably, was a Microsoft server which McGill uses. So my concern is that maybe it looks bad to have something coming from my laptop, which is portable, as a first MTA. Maybe that is wrong. When I'm at work, the same laptop has a fixed IP and an IP name, but this was sent from home. I don't really know what I'm fighting, but I'm trying to minimize reasons to reject my emails. So if (especially when at home) I sent from a fixed IP machine at work (ssh pipe) rather than from my laptop, maybe it would be better.
Asked by CPBL (121 rep)
Jul 15, 2020, 04:02 PM
Last activity: Aug 26, 2020, 08:00 AM