How to use HELO with PHP’s mail() function

I originally wrote this for the HELO-community tracker, and it was subsequently published on BeyondCode’s blog, but I wanted to publish it here as well.


HELO works very nicely if you’re sending via SMTP using PHPMailer, SwiftMailer, etc. – but lots of apps and scripts rely on PHP’s clunky old mail() function, which isn’t nearly as easy to deal with, and harder to point at HELO.

You can configure “proper” mail servers like postfix to work as a local relay, but it’s horribly complicated and confusing to set up. Fortunately there are simpler alternatives that are much easier. Searching for local relay tools (what this is) will usually point you at ssmtp, however, that doesn’t work on macOS. A better option for macOS is msmtp which is present in homebrew and works perfectly. I usually run HELO on localhost port 2500, and I configure msmtp with a config file like this, which enables the authentication that HELO requires:

defaults host localhost port 2500 tls off undisclosed_recipients off account default auth plain user test password password

To make the PHP mail function use msmtp, you need to configure the sendmail_path setting in your php.ini file to point at it:

sendmail_path = /usr/local/bin/msmtp -t -i

If you’re using homebrew’s PHP package on macOS, I recommend putting config changes like this in a separate .ini file so that it remains update-safe. For example I put mine in /usr/local/etc/php/7.4/conf.d/marcus.ini.

With those two things in place, PHP’s mail function will submit to the local msmtp binary, which will then relay the message to HELO over SMTP.


Sending via this this route using PHPMailer is very simple because mail() is the default mailer, so you don’t need to configure anything:

<?php use PHPMailer\PHPMailer\PHPMailer; require 'vendor/autoload.php'; $mail = new PHPMailer(); $mail->setFrom('from@example.com', 'First Last'); $mail->addAddress('whoto@example.com', 'John Doe'); $mail->Subject = 'Say Hello to HELO'; $mail->Body = '<h1>Hi!</h1><p>This is my HTML body</p>' $mail->AltBody = 'This is a plain-text message body'; if (!$mail->send()) { echo 'Mailer Error: ' . $mail->ErrorInfo; } else { echo 'Message sent!'; }

The Stack Overflow Antipattern, part 2

I enjoyed Riggraz’s observation of “The Stack Overflow Antipattern”, and it made me think of another very similar pattern that I see a lot on Stack Overflow, but it occurs after the pattern that Riccardo describes, and I thought I’d outline that here.

Image by wal_172619 from Pixabay

I answer a lot of questions on Stack Overflow. I ask very few, but I’ve still fallen into this trap myself.

Once you’ve been through Riccardo’s antipattern (ignoring the other antipattern of those that don’t even make it to step 1), you are here:

  1. You’ve searched and found some random results
  2. You’ve read some SO questions that were in those results
  3. You’ve still not found a solution

If you’ve got this far, the breadth of the question you want answering has probably been narrowed a little (which helps in its own right: searching is a mild form of rubber ducking), and probably contains the basis of a worthwhile Stack Overflow question.

So you focus on the problem, write it up, and (assuming this rubber-duck exercise didn’t lead you to a solution) post the question, and answers and comments appear reasonably quickly (hey, Stack Overflow rocks!). But often these responses are bogus, half-answers, or raise further questions. It’s at this point that we see the same “not taking the time to think” that Riccardo observed. You are so focused on the original question, you become incapable of solving a far simpler follow-on question.

Here’s a small example I often see:

“I’ve seen docs and code referring to autoload.php, but I can’t find that file”

Searching for autoload.php will find a zillion irrelevant results, because pretty much every PHP project in existence has one. So the question is posted on SO. There is a simple answer to this question, which is

“install composer, run `composer install`, and it will create the autoload.php file for you”

This inevitably leads to the follow-on question:

how do I install composer?”.

This is a new sub-problem, but one that is instantly solvable by searching because it’s far less ambiguous. However, this is where the abdication of thinking kicks in, and rather than actually doing that search, you ask in the SO question comments, and sit around waiting for an answer from Someone Who Knows™ that posted an answer to the original question. This is frustrating for the answerer, who knows that the asker could find the answer to this question far faster by searching for themselves, but they choose not to because their thinking is turned off. There’s also an element of panic – the asker has obtained the attention of someone capable of understanding their problem, and doesn’t want them to escape before they have addressed the full recursive stack of sub-problems. This has led to the existence of passive-aggressive responses like LMGTFY, which are demeaning and condescending, but reflect the frustrations of those who answer questions.

What’s weirder is that I have observed myself doing this very thing, and I’ve sometimes had to stop myself posting trivial follow-up questions without thinking. Avoiding having to think is evidently a compelling driver.

I emailed Riccardo about his article with some of the thoughts that led me to write this, and he came back with another interesting observation: This loss of confidence that leads one to post trivial follow-up questions is very much like imposter syndrome. Having had to ask a question in the first place can provoke feelings of embarrassment or inadequacy, and anyone that responds in a positive way will appear to be in some way superior, which is fully expected, but at the same time provokes feelings of “we’re not worthy”, further reducing one’s confidence to be able to deal with even simple problems.

We’re not worthy

I know that Stack Overflow (and GitHub issues) can sometimes be harsh on new users, and old hands (like me) can forget what it’s like to be a beginner. It can be very frustrating to answer questions that have been answered many times before (“my PHP script just gives a white screen”), and I’ve occasionally found myself editing my initial reaction to avoid unkindness. In those situations I usually try to overcompensate by offering more general advice about how to avoid getting stuck in dead-end situations like that, rather than just answering the precise question asked.

In PHPMailer I have tried to head off support questions before they arise by adding links to documentation in error messages, but it doesn’t stop people posting questions like this:

I have this error:
> 2020-05-16 07:28:11 SMTP connect() failed.
> https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting

I have been stuck on this for 2 weeks, and I searched the entire internet three times
Where can I find out how to fix it? You must help me urgently!

I don’t really know what to do when faced with this. Posting a substantive answer is probably pointless – if they have not read what’s right in front of them despite their evident frustration, chances are they will not read any answer you post either, especially since it will only contain exactly what’s in the link provided anyway. Sometimes the best thing to do is vote to close the question, usually as an inevitable duplicate. I see very similar things happening in GitHub issue templates – askers delete the boilerplate text, removing something which would usually help them solve their exact problem in a few seconds, but they go out of their way to make the process take longer and involve others unnecessarily, because apparently not having to think is a more attractive proposition.

I’ve also considered pushing in the other direction, such as by adding “delete this line from the debug output before posting questions about it, or your question will be ignored” as a way of enforcing reading the error messages, but that’s unkind.

I’m not sure how to address the abdication of thinking issue though. Perhaps offer up search results derived from comments or answers, much in the same way that Stack Overflow does when you first post a question? There are probably extensive psychological studies on this pattern of behaviour, and it may well have a name, but that’s a question for another Stack Exchange site.

Should I build a PHPMailer video training course?

I spend a lot of time working on PHPMailer, and even more answering questions about it on Stack Overflow, yet gain very little from doing so. There is a certain amount of professional pride and reputation involved, but that doesn’t pay the bills. I am lucky enough to have a few GitHub and Patreon sponsors (thank you!), but that doesn’t amount to much. The same questions come up again and again, and repeating the same answers over and over, to people who are convinced that they must be the very first person ever to have had trouble sending email through GoDaddy, gets dull and tiring. I also run Smartmessages.net (a privacy-first email marketing service), so I am continuously exposed to large-scale email issues that small senders never have to worry about, but that are near-impossible to find advice about.

Email is a funny thing; it’s been around forever and is absolutely taken for granted, but it’s horribly complicated (way more so than, say, HTTP), and many developers, especially new ones, have absolutely no idea how it works – hence the repeated mistakes. Email grows more complex by the year, with the addition of things like SPF, DKIM, DMARC, ARC, MTA-STS and more. Some of it is really quite tricky yet the resources available for it either suck or are decades old. I’ve previously pitched book proposals to popular publishers (including O’Reilly and Packt) on “Modern email”, but have always been rejected on the basis that it’s not of interest or “outdated”, even though email usage is forever growing and changing.

So I’ve been thinking about putting together a training video course on using PHPMailer, diagnosing related problems, and using email in general. Such courses are apparently very popular, though I have to admit to not using them much myself, preferring text. I’ve been heartened by the success of projects such as Christoph Rumpel’s Laravel Core Adventures, along with his valuable advice on how he built that. I’ve been impressed by the lovely Jeff Geerling‘s dedication to his ansible book and audience, and have contemplated going the self-publishing route, but a book is a really big commitment, especially on such an enormous subject as email. Video courses are a bit more flexible, though keeping them up to date has its own issues, as Jeffrey Way has said about his amazing output on Laracasts.

The big issue is my audience. I know that it’s going to be primarily junior and novice developers with little experience needing help putting together their first contact form, so it needs to be pitched quite low, at least to start with. I gather that the primary feeder for video courses is social media, but my social media profile (principally Twitter; being a privacy advocate means I really don’t want to go anywhere near Facebook) is mainly more experienced developers, who are probably not the ones who need this kind of help, though you never know – it may just be my impostor syndrome assuming that all these clever people already know about this stuff!

In summary: there is fertile ground for such content, there’s little competition, I’ve got all the experience, equipment, and position needed to do it, but I need some help and encouragement with putting together a platform and reaching my audience. Finally, since I really need to dogfood this sort of thing, please sign up to my PHPMailer mailing list!

Minimal jQuery and extensions in Laravel

I recently needed to add a simple tag editor to a form input. I initially thought that Vue might help with this. That was a big mistake! Vue is seemingly pretty hopeless for this kind of thing – you can’t really use it for “sprinkling” JS elements, and progressive enhancement is a complete non-starter; that’s really more the domain of old-school jQuery, though I hear good things about alpine.js for this kind of enhancement. I learned a lot about Vue that I hadn’t planned on doing, but the overall impression was that it was simply the wrong tool for the job. I am not interested in building an SPA, and I’m certainly not out to rebuild my entire site just for sake of a single widget! My analogy for Laravel and Vue is like oil and vinegar in a salad dressing; they will happily coexist in the same bottle and taste great together, but they really like to be separate.

So, back to jQuery I go. jQuery was disabled by default in Laravel 6, but it’s just commented out in resources/js/bootstrap.js. It’s already included in the npm packages.json config file, so running npm install loads it into node_modules. I was really unclear about how additional JS modules should be added to Laravel using Mix. This was also a bit confusing because there isn’t really much you can point at and say “that’s mix”; it really comes down to what you put in webpack.mix.js in the project root and the npm run devscript that builds assets. However, the main thing that this does is load app.js, but then I found that things like this should be added in bootstrap.js (which is loaded by app.js) rather than adding them to the the mix config.

So the aim of the exercise was to add a tagging UI widget that takes a standard text input full of comma-delimited terms, and turns it into a pretty clickable tag element. Out of many worthy options, I settled on Tagify. After adding it with npm i @yaireo/tagify --save I had trouble figuring out where to actually load it from, but eventually I got it working by adding:

require('@yaireo/tagify/dist/jQuery.tagify.min.js');

to my bootstrap.js file, and evidently this looks in node_modules/to find the file without any additional help. After this I created a script in public/js/editthing.js (because inline scripts are worth avoiding if you’re serious about your CSP) that turned the standard input into a tag widget:

$('#tags').tagify();

and this script was loaded from blade using Laravel’s asset helper, which creates appropriate base URLs for public resources:

<script src="{{ asset('js/editthing.js') }}"></script>

I sometimes find Laravel docs and articles infuriating – there is often both too much and too little information at the same time, or they say things like “just add it to mix”. Many articles on simple subjects like this subvert Laravel’s features to shortcut to “working” (but ultimately counterproductive) solutions, and I wanted to approach this “the Laravel way”. For that reason I thought I’d make detailed notes for these very simple steps that I couldn’t find written down together elsewhere!

HTH