SendGrid e-mail server silently converts plain text e-mails to HTML, losing line breaks in the process. They have some reasoning on why this is a good idea, but I do believe most silent conversions are evil, since they violate the rule of least astonishment.

I have added a plugin to WordPress that sends e-mail notifications to a commentator when their coment is answered (this should have been a standard feature, but that’s another matter). It almost worked: the notifications did arrive, but all squished in one line. So, if the original message was

Line One
Line Two

it would show in the e-mail as “Line One Line Two”.

Something along the way was losing the line breaks, and I had quite a few moving parts in the pipeline: the plugin, the WordPress, PHP, Apache, sendmail on my server, the mail client and any of the SMTP relays in between.

I verified that this is not the plugin, since it sends a plain text e-mail only. After some digging I noticed that the converted HTML e-mail has some embedded image that refers to “Sendgrid”. I host my blog on Azure, and Sendgrid is the mail server they offer. And indeed, it turns out Sendgrid silently converts plain text e-mails to HTML, losing line breaks in the process.

Silent conversions are evil: this is why C++ ended up having the explicit keyword. Silent conversions that lose information are especially evil. Frankly, Sendgrid should not have done it, or at least should have made it an opt-in feature, rather than the default.