EDIT: Thanks y’all! I got this working by installing mutt and configuring it with my Gmail info. Please note the warning from u/jherazob below–if this were something mission critical I would not want to rely on this solution.

================

Noob question incoming, thanks in advance for any help with this!

I have a specific use case in which I want to send an automated email or text to myself once a day (the message is different each time–otherwise I would just set an alarm, lol!). I’m running Pop_OS on an old desktop computer. Where I’m stuck is getting an email to successfully send from the command line. I’m looking for easy-to-follow instructions that would help me do that, and none of the articles or videos I’ve come across thus far have helped.

I’m aware of Twilio and other services that send SMS messages, but I’m looking for something free. Especially since I only need to text one person (myself), and infrequently at that.

Below is my attempt to send an email with the telnet command. Nothing ever came through…

XXXXXXXX@pop-os:~$ telnet localhost smtp
Trying ::1...
Connected to localhost.
Escape character is '^]'.
220 pop-os ESMTP Exim 4.95 Ubuntu Sun, 07 Jan 2024 15:12:28 -0500
HELO gmail.com
250 pop-os Hello localhost [::1]
mail from: XXXXXXXX@gmail.com
250 OK
rcpt to: XXXXXXXX@gmail.com
250 Accepted
data
354 Enter message, ending with "." on a line by itself
Subject: Test
Body: Is this working?
.
250 OK id=1rMZW4-0002dj-Uy
quit
16 points
*

I see several issues with your SMTP session.

First, gmail.com will be protected by SPF and DKIM and your message will likely be flagged as spam (or outright rejected) because it’s clear that you’re not sending on behalf of the real gmail.com.

Second, commands should be in all-caps. A server may accept or reject lowercase keywords.

Third, you need to leave a blank line between the mail headers and the body, so that part of your session would look like so: …

DATA
354 Go ahead
From: ...
To: ...
Subject: ...

This is the first line of text.
This is the second line.
.
250 Queued

Having said that, many servers will require an encrypted connection (SMTPS), many ISPs will block port 25 for residential customers as an anti-spam measure (so your local mail server may accept the message from your script but be unable to forward it), ESMTP should be preferred over SMTP etc.
If at all possible, you should use a full-featured mail library for this and use your ISP’s own mail server.

Doesn’t Pop_OS come with a sendmail command?

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1 point

Thank you so much for the detailed reply! I’m learning a lot from this thread

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1 point
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10 points

If you’re ok using Signal I use https://github.com/AsamK/signal-cli for sending myself texts through command line

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4 points

Oh sick, thank you! I’ll check it out

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3 points

Awesome, I actually use this docker container that implements it https://github.com/bbernhard/signal-cli-rest-api

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7 points

Implementing a telegram or discord bot might be easier

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6 points
*

Your current approach of talking raw SMTP is likely to be more hassle than is worthwhile, and since the days of permissive SMTP servers are long gone, might not work at all.

Since you appear to be using an Debian-based Linux distro, I suggest this approach:

  • If you don’t specifically need exim, consider replacing it with the lightweight dma package (DragonFly Mail Agent): apt install dma
  • Configure dma (or exim) to use your ISP’s SMTP server as a smart host. (Or the Gmail SMTP server if your ISP doesn’t provide one.)
  • Use the /usr/sbin/sendmail command (which comes with dma or exim) to send messages from your scripting language of choice.

If you prefer to receive messages as SMS, note that most major mobile carriers maintain an email-to-sms gateway for this purpose. Some web searches will probably lead you to the one for your carrier. They usually accept email at an address like 123456789@sms-gateway.example.com

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Thank you so much for this!

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6 points

Yes, you can. Though as another commenter mentioned, doing it like you currently attempted to, is way too much of a hassle.

That is, don’t try and negotiate your own SMTP session and content. Being POP_OS is Ubuntu based, you should be able to use the mail command from mailutils package

echo "Is this working?" | mail -s "Subject" recipient@email-address.org

Also might want to consider something like Apprise (Everything and the kitchen sink) or NTFY (Does one thing, does it well) for other types of notification methods.

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2 points

This didn’t work for me, but what I’m gathering from the other comments is I need an SMTP configuration on my machine before I can do this. Thanks so much for the help!

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2 points

If you use gmail you can create an app password that can be used for this. Or if you have a domain you can e.g. use free tier zoho mail or something to create an email address.

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