Lies we tell ourselves about email addresses

https://gitpush--force.com/commits/2026/06/lies-we-tell-ourselves-about-email/

166 189 1 month ago

I enjoyed the deep dice. A lot of sensible advice, and enjoyed the deep dive. A lot of articles do not get a lot of that as right as this article does.

Anyone who also enjoyed it would probably get a kick out of my article on the same subject that goes into the regex (which has some valid use cases): https://hackernoon.com/on-the-practicality-of-regex-for-emai...

amiga386• 1 month ago

Add the lie "emails are delivered instantly, so the user can click a link I email them within 1 minute"

And the lie "users always read emails on the same device they're logging into a website with"

And the lie "users can always view HTML email so no need to send a plaintext equivalent, especially if I have a long complex URL I want them to click"

And the lie "Clickable links sent in email are more secure than passwords so I'll stop supporting passwords and instead rely on email delivery of a link for all logins. Whoever clicks that link first is definitely the user who wanted to log in"

wodenokoto• 1 month ago

If you have a password reset form, you probably already have a log-in with email with extra steps functionality.

CPLX• 1 month ago

Clickable links sent in email are more secure than passwords so I'll stop supporting passwords and instead rely on email delivery of a link for all logins

God, I fucking hate that.

I have a fucking password manager, I have various machines and things open. Just let me fucking log in.

If anyone is reading this who is in charge of the internet please stop doing this.

denkmoon3• 1 month ago

The people in charge of the internet are "cybersecurity" "professionals" who can't even follow NIST guidance.

roygbiv2• 1 month ago

I seem to spend half my life logging into thing's, confirming 2fa,confirming biometric data. Then when I go back to the first thing it's timed out and I have to sign in again.

anon7000• 1 month ago

So agreed. It’s fucking crazy. Password manager is so much easier and more secure. If you do this dumb email or SMS OTP flow, at LEAST support passkeys for my password manager!

It’s wild that they’re like “it’s more secure to not have a password” and then choose two unencrypted delivery mechanisms for the very short OTP.

Sure, people who reuse passwords are not secure. And fair, I guess it’s a tragedy of the commons. But at least continue supporting it and make it dead simple for password managers if you actually care bout security

Terr_3• 1 month ago

There's a landlord/apartment portal where the whole login process has changed to be:

1. Enter username (e.g. an email)

2. Choose from either email or SMS on file

3. Enter the code you got somehow through the respective unencrypted channel

Given that this same site is involved with bank-account details for payment, I am concerned...

paradox460• 1 month ago

I'll heap email and sms based otp into that

I have many ways to generate totp codes. All of them are vastly more convenient than sending me an email or sms

trumpdong4• 1 month ago

If you try to create a Discord account with Firefox Klar as your default browser, on Android, immediately upon signing up you'll be banned. I have to assume this is because it clears cookies and thinks you're a bot farm.

nosioptar• 1 month ago

When I had protonmail, I often wouldn't get emails for hours, sometimes a day.

Most other providers I've used range from instant to a few minutes.

Terr_3• 1 month ago

And the lie "users always read emails on the same device they're logging into a website with"

Or the same browser, or the same browser-profile. For example, on my phone I have external links (from other apps) opening in incognito mode by default.

butvacuum2• 1 month ago

I don't think it's about security. It's about fobing off password resets on somebody else.

tatersolid• 1 month ago

This is market-dependent. We offer email OTP login for small business customers because it is “poor man’s SSO”. You’re basically validating the recipient is still at the company, able to receive at their work email.

Larger customers have IT staff and set up OIDC or SAML with us. We don’t add an SSO tax.

technion2• 1 month ago

Claude, for my non Gmail domain, expects me to click a magic link on every device I wish to use it. Its wild that a product like that cannot take a password, or a passkey.

JdeBP4• 1 month ago

I'm surprised that this has not triggered all of the reminiscences of sitting running mailq at intervals for hours to watch mail that hasn't even left the local sending machine yet.

teo_zero3• 1 month ago

The plus sign is a pet peeve of mine, too. But I stopped keeping a list of bad sites when their number has become double digit!

jeffbee3• 1 month ago

This article says that Gmail can't handle address literals. I personally wrote the IPv6 address literal support for Gmail, so this annoys me. I just tested it and it shortened "[IPv6:2001:etc:etc::192.etc.etc]" down to "@2001" then generated an extremely terse mail delivery subsystem notification that I've never seen before. Which is why you should never just rewrite software without understanding why all the test cases are in the test suite!

farfatched5• 1 month ago

Could they have consciously chosen to remove that functionality?

E.g. to simplify code, or if they wanted all mails to have a domain (if, for example, they wanted to integrate with reputation systems that were domain oriented)?

jeffbee3• 1 month ago

Based on the incredibly basic bounce message, I suspect the problem is that the frontend eats the address before it even gets to delivery.

To your question, yes any product decision is possible, but enterprise/government people are surprisingly demanding about this stuff working because they have extremely weird requirements for routing mail to and through legacy systems. So I bet this still works at the mailer level and is broken in the UI.

thwarted2• 1 month ago

"[IPv6:2001:etc:etc::192.etc.etc]"

I'm trusting this is a throwaway example and that you used a real IPv6 address literal in this test, without the "IPv6" and with only colons and no dots (unless you mean to use v4 mapped address with dots)? Because this IPv6 literal is so malformed that I'm hardly expecting it to do something sane and changing that to "@2001" is nasal-demons quality undefined behavior. I tried with this exact literal and it let me send it but then there was a tiny red pop-up at the top of the gmail interface that said "could not be delivered, check your network connection" (which is odd; the same kind of pop-up that appears in gray when you legitimately are not connected to the internet) and it ended up in my drafts with the To: field empty.

I just tried to send a message to a "test@[" my current IPv6 address "]", and gmail told me

    Error
    The address "test@[«redacted»]" in the "To" field was not recognized.
    Please make sure that all addresses are properly formed.

This address doesn't have an MDA listening on it, but it didn't accept it enough to give me a non-delivery notification, it didn't even let me send it. gmail did accept an IPv4 address literal in brackets, although it hasn't given me back a non-delivery notification. What it stuffed into my Sent folder for this message has the square brackets stripped and the IPv4 address appears right after the @.

jeffbee3• 1 month ago

All address literals other than IPv4 must be prefixed by a tag, such as "IPv6:". The form that I gave is a syntactically valid v6v4 address literal.

https://datatracker.ietf.org/doc/html/rfc5321#section-4.1.3

farfatched5• 1 month ago

It’s likely that more people out there are being filtered by badly-implemented form validation than there are being filtered by their own need of hand-holding.

I wish this was asserted with evidence. The author might suggest this because they have unrealistic views of some users.

In the year of our lord 2026, you can reasonably expect your users to know how to type their own email address - or even better, auto-input from their OS, browser, keyboard app, or password manager.

This really depends on who your users are.

I have multiple family members who have healthy memory, but can't accurately remember their email address everytime: the localpart, the domain, the syntax, everything.

Sending an email verification isn't sufficient, because if the user has typo'd ".com", they might never receive that email, and the user might never be back, or then have to escalate to support.

Meanwhile, if a site is opinionated on TLDs, they might prevent those users facing issues.

I'm sure there are many sites were users have a large variety of odd email addresses, but also there are sites that cater to mostly non-technical users within 1-2 locales, and so may find the friendliest UX is having opinionated validation.

trumpdong4• 1 month ago

There's something you can do in between - you can check the domain has an MX record.

farfatched5• 1 month ago

Yes, and the MX check is pretty simple to implement.

But it is still lots more complicated than copying some imperfect email address regex, and for many sites, it's unlikely to even be worth spending much more effort than that.

Realistically, many sites can defacto choose to accept email addresses of few patterns. If a user's email address happens to be rejected, then they are either a non-technical user who quickly learns that they need a more commonly accepted email address, or a techie, who keeps a backup email address for these cases, and rightfully holds a grudge.

Most sites just aren't going to care enough to do anything more complex, for annoyed techies.

See also, IPv6 support.

And yes, I get annoyed if a site doesn't accept my domain-under-a-less-common-tld, or doesn't support IPv6. :)

account4212• 1 month ago

Technically you don't need an MX record to receive mail. From RFC 5321:

If an empty list of MXs is returned, the address is treated as if it was associated with an implicit MX RR, with a preference of 0, pointing to that host.

I don't know if most MTAs allow this though.

rmunn• 1 month ago

I have multiple family members who have healthy memory, but can't accurately remember their email address everytime: the localpart, the domain, the syntax, everything.

I got Gmail early enough that I have (my first name) dot (my last name) at gmail dot com. About twenty years ago, I started getting strange emails. At first I thought they were spam, because they were addressed to me by name but I had never joined those sites. Eventually I figured out that they were addressed to (my first name) (my last name) at gmail dot com. Which Gmail treats as the same address as the one with a dot in between.

Since I had never ever given out a version of my email address without a dot in the middle, I eventually figured out that these emails were meant for someone else who shared the same first and last name as me. But since I don't think Gmail would allow one person to register john.example@gmail.com and then later allow someone else to register johnexample@gmail.com, my name doppelganger must have registered firstnamelastname@yahoo.com, and then forgot the domain and given out firstnamelastname@gmail.com when asked for an email address. And probably never noticed that they weren't receiving emails like "Dear customer, thank you for purchasing (product). Would you like to try (other product)?", so they never realized that they were giving out the wrong email address.

jcranmer2• 1 month ago

Randall estimates in the alt-text of https://xkcd.com/1279/ that there's about ¾ of a million people who just use somebody else's email on gmail without realizing it's not their email address.

Semaphor• 1 month ago

I also have first.last@gmail.com (which I don’t use anymore, and just keep around), I get all kinds of private mails. Contracts, invoices, confidential material, private photos.

And of course, also automated signup mails, newsletters (which I make sure to block and report as spam, unsubscribing is a feature for newsletters that are opt-in), transactional mails etc.

People really suck at knowing what their e-mail is. The private mails are down to 1/month, the others to ~3/week, but it used to be much higher for both categories.

Oh and of course there is some kind of weird scam going on where spammers on German classifieds (Kleinanzeigen) send an e-mail to firstlast@gmail.com for whatever public first and last name of the lister is, and ask if the product is still available. No link, nothing. And all sent via gmail which has by an overwhelming majority become the biggest sender of spam for me. I guess they are trying to get someone to reply and then do some manual scam or something.

f_fmail3• 1 month ago

my name doppelganger must have registered firstnamelastname@yahoo.com, and then forgot the domain

Alternative explanation: A hastily scribbled "@ymail.com" (along with its relative infrequency) can look to many people like "@gmail.com".

ycombiredd• 29 days ago

Hey! Neat to see some more folks that have a story to tell about the oerhaps unintended side effects of the way the dot was implemented in gmail addresses.

Reading these dot-related comments reminded me that I once made one here about how I was able to leverage this possibly asynchronous dot-handling at gmail. Because the story is a bittersweet sentimental one for me I had to go back and read it now, and though I am sitting here with bad allergies streaming down my face, it also felt really nice to remember that.

I know this is a bit of a sideways comment, and I apologize for that but it isn't often I am overcome with emotion on HN, or on the topic of email addressing, and well, I appreciated the opportunity to re-read it now. Thanks.

You might find my gmail dots story interesting too. It's a little long, but the dot-character portion begins about a third of the way down in my comment:

https://news.ycombinator.com/item?id=46539424#46541149

Cheers!

wolrah• 1 month ago

That's why the article says "verify, not validate". Send an email, have a process for them to confirm they received it.

If the user gets the email and completes the validation, the email is valid. If they fucked up, they don't get the email and the account never gets created.

No one ever gets prevented from creating an account with a legitimate email address, as opposed to "opinionated validation" where that absolutely will happen. Speaking from years of experience having a .info domain which isn't even all that odd, and at one point using gmail-style + addresses regularly. "Opinionated validation" has forced me to use my .com domain without a plus dozens of times.

I know part of this is intentional, those who know they plan to sell your email addresses don't want you to use the plus addresses, but that doesn't make the advice to not filter addresses any less correct.

layer82• 1 month ago

While I’m opposed to opinionated validation as well, you seem to be missing the issue it tries to solve, which is the user mistyping their email address, not receiving the verification email, and either thinking everything is fine, or thinking that the process is borked, and in any case not proceeding and not becoming your customer. The goal of opinionated validation is to inform the user about an incorrect email address immediately when they are entering it, so they can correct it right away.

TZubiri2• 1 month ago

I have multiple family members who have healthy memory, but can't accurately remember their email address everytime: the localpart, the domain, the syntax, everything.

But you can't do anything about that except asking them to validate their address with an email.

If you can catch 50% of user errors with some complex regex, but the other 50% such errors are uncaught, is that of any benefit during sofware design? No, because you still have to solve that problem, probably with email validation by code. You have reduced your workload by 0%, you just split it into 2 parts (unnecessarily).

farfatched5• 1 month ago

If you can catch 50% of user errors with some complex regex, but the other 50% such errors are uncaught, is that of any benefit during sofware design? No, because you still have to solve that problem, probably with email validation by code. You have reduced your workload by 0%, you just split it into 2 parts (unnecessarily).

In your example, the benefit is that users recover from the error 50% of the time at the time of registration, so it doesn't interrupt their workflow. Further, the fallback case (of contacting support, or enacting email validation, if a site chooses to implement) will see a dropoff in successful onboarding.

account4212• 1 month ago

It is absolutely beneficial to catch 50% of errors earlier than you otherwise could. If validation fails the user is notified immediately. If you don't wait the user has to wait a bit in case the mail is just delayed.

sohex• 1 month ago

IIIRC in terms of clients mutt (&co) will actually handle “@“ in the local part correctly.

But the real reason I do that is just because I just like to sit in anger whenever this breaks the user experience because of programming errors or inconsistencies.

Genuinely delighted by the fact that I’m not alone in that.

gerdesj2• 1 month ago

Email is just like physical mail and thankfully just as endearingly human (sometimes).

Once upon a time (1970/80s) I lived on and off in a mystic land called West Germany. Our postal addresses ended with incantations such as BFPO 40.

Around 1985ish my granny send a Christmas card to us. I should note that she was at this time nearly seventy and sadly suffering from Parkinsons. She addressed the card, in rather crabbed but legible handwriting, to:

Graham and Heath BFPO 40

My mum's name is abbreviated - her daughter. At that time Rheindahlen (nr Moenchengladbach) had a pretty large contingent of Brits in it - it was HQ (BAOR).

The card arrived well before Chrimbo and it took about a week judging by the post mark, which was petty normal in those days. She shoved it into a post box in Ipplepen, nr Newton Abbot, Devon and it found its way to an obscure address in another country. I seem to recall she also forgot the stamp but it still got through.

I'm sure mail like that becomes a point of honour to deliver and HM PO and BFPO did the job admirably.

That attitude is how email MTAs are generally designed to work. They cling on to the good old days and sadly the world is a bit shit. Case sensitivity ... lol!

8n4vidtmkvmk2• 1 month ago

New rule: when emailing someone, you need to include their name. If you do that, the email delivery gods will correct typos in your email address.

cjs_ac• 1 month ago

Bill Bryson claimed to have received a letter addressed to ‘Bill Bryson, Writer, Yorkshire’.

I have some cousins who live in a small town in Australia where the houses have neither names nor numbers. You just address the envelope to ‘<name>, <street>, <town>’, and it’s the postie’s responsibility to know where everyone lives. (‘Postie’ is the official job title in Australia Post because it’s gender-neutral.)

KurSix4• 1 month ago

I love these examples because they show that addressing has never really been as formal as we like to pretend

eythian• 1 month ago

I lived in mildly rural NZ back in the day and it was the same, addresses were "name, street, RD# (rural delivery route number), town" and your mailbox had your name on the side (and a flag you could put up if you wanted mail collected.)

Some time roughly mid-nineties we got numbers but originally they were just for emergency services, only later were they also for post, but I seem to recall the whole rural delivery system may have changed somehow around then too.

wang_li• 1 month ago

Until 2025 Carmel-by-the-Sea in California had no street addresses. The houses have names or you just have to know who lives in which building. They also didn't have postal delivery, they all had to go to the town post office and pick up their mail.

FinnKuhn2• 1 month ago

When I was a child I sent a postcard to my grandparents. I forgot to put the house number and addressed the letter to "Oma und Opa" (Grandma and Grandpa). Logically it should not have been delivered successfully.

Thankfully though, the postal worker knew my grandparents had grandchildren and therefore just asked the potential recipients for the name of their grandchildren to determine, which grandparents the postcard was addressed to. To me it's still a miracle that it got delivered at all.

pseudohadamard2• 1 month ago

Up until at least the 1970s you could do this with smaller places in Germany. My mother has some old letters with addresses like "$surname, $village near $larger-village, West Germany". I assume it was routed to $larger-village, they passed it on to $village, and everyone there knows everyone else so the postie dropped it off the next day.

jiveturkey2• 1 month ago

TL;DR: Don't overthink it, just send a verification email.

pretty bad advice, if taken only as written, without adding more flavor on top.

the major email providers will penalize you if you generate too many undeliverable emails. thus, if you just send a verification email without any pre-validation, it's pretty easy to get into a DoS situation where current/valid users don't get important email sent to them, or that email is significantly delayed, plus incur huge operating cost to resolve the problem.

some form of rate limiting is needed, plus IMHO it's better to use a verifier service or your own heuristic or ML model to test for email validity including valid but fake/spammy/disposable addresses.

sorry, but we are way past the point of being able to have nice things, esp. when we're talking about email.

the "lies" part of the content is great. people do assume all those wrong things. however the TLDR is just wrong, and potentially harmful.

trumpdong4• 1 month ago

I think the only way to deal with that right now is to hire a company whose job is to deal with it. They'll random-check your outgoing emails are indeed what you say they are, and they maintain a reputation with the big providers for checking it properly.

What pre-validation could you do that would possibly be useful?

jiveturkey2• 1 month ago

entropy check, for one

teo_zero3• 1 month ago

the major email providers will penalize you if you generate too many undeliverable emails.

I suspect the rate at which new users may try to create new accounts and type a wrong email address is too low to be noticed by reputation metrics.

AndroTux4• 1 month ago

there's bad actors that use bots to sign up to websites using bogus data.

ashley952• 1 month ago

This is cute and all. But for anyone coming here for real-world advice: just use a regex, normalize to lowercase, and surface any errors to users so they know if their email got rejected. This will avoid 99.9% of issues and work for 100% of real human users. This is what everyone else does, and if you have a user with an esoteric email, they will still be able to furnish another one that passes this validation.

pif• 1 month ago

Display a warning and propose to edit instead of blocking the operation: your customers will be happier!

tracker12• 1 month ago

Verify all email address entries before you start using it... I absolutely HATE how much garbage I get because a few people don't understand you actually have to get an email address before you start using whatever you like.

ashley952• 1 month ago

Right, maybe I worded my response a bit vaguely. Of course you need to do an opt-in and verify them.

My point was rather that if you are operating a service with human users, there is no need to deal with quoted local parts, mixed-case, non-ascii, etc. You will just run into bugs (oh, the user signed up on an iPhone and the email field was auto-capitalized and now they can't find their account?) for almost no marginal benefit.

riddley• 1 month ago

I have a gmail address that at least three other people think is their address. I constantly get emails for the dumb stuff they sign up for. NONE of them ever have an "I didn't request this" link. I mean, I get it. That won't make them money, but oh man is it annoying.

JimTheMan• 1 month ago

I get scammers using my email to sign up for websites, but they very obviously cannot login to my account. I often wonder what is in it for them. I'm sure someone on HN can tell me!

AndroTux4• 1 month ago

I assume they just need a valid email address to put in and hope they can use the service without email verification.

vintermann• 1 month ago

Commission schemes, possibly. Sign up with their code and they get something out of it. So they submit 10000 harvested addresses, and hope some small % of them think it's something they signed up for and complete the registration process.

You'd think big companies would know better than enlisting spammers to spam on their behalf, but I'm pretty sure Netflix had a scheme like this a few years ago. "Grow at any costs" sites like streaming or social media are probably happy with a tiny bit of plausible deniability for their spamming.

zephen• 1 month ago

I have exactly the same problem.

I mean, I get it.

I don't.

Seriously, that's a huge fricking red flag. Obviously, most of those companies I would never do business with anyway, but this puts it over the line for all the others.

If they don't understand the first thing about validating their putative customers' emails by, you know, sending an email saying "is this really you?" then they've completely proven their technical incompetence.

The worst one is robinhood. I have two different email addresses that different people have used to sign up for robinhood accounts (back when they were giving anybody an account).

Occasionally, I tweak them about sending me shit.

"Sure! Just send us a copy of your photo ID to prove you're not that person."

Nah, bro, you've proven you're clueless, and there's no way I'm sending PIA to clueless people.

hnfong• 1 month ago

The weirdest time was when I got on a girl sorority email list. Told them they got the wrong email a couple times, gave up, and just added a mail filter...

rimliu• 1 month ago

I feel your pain. My gmail address is just my first name, and oh boy, don't half of the people sharing the same first name also think they share my email.

undebuggable• 1 month ago

I have the same with my email address. There seriously exist people out there who think that if they start to give away everywhere an email address, this email address will become theirs. Then there are many service providers and institutions who don't verify an email but simply start sending stuff to it.

account4212• 1 month ago

I just report those as spam every time.

cestith• 1 month ago

I get these all the time. The most fun was probably when I was given and building layout, door at which to arrive, schedule, and security information to get into a pro sports arena for a game as an employee of some vendor. The least fun was probably when I ended up talking to some drug company’s general counsel about why it’s not okay to send information about a discount program for a specific drug that treats one specific disorder with a bunch of personal information about the patient to an unverified email address. I went on to explain how their tech staff could prevent that, and remind them of the fines and possible jail time involved with HIPAA and HITECH violations.

macintux• 1 month ago

I've become email acquaintances with two people who have similar iCloud addresses as mine, since I've been forwarding their mail for years now.

miningtcup• 1 month ago

I would like to point out that the "suggested" validation pattern, ^[^@]+@[^@\s]+$, can filter out valid addresses. "user@something"@example.com is a valid address, and excluding @'s in the user part rejects it.

zenoprax• 1 month ago

"user@something"@example.com is a valid address

I appreciate your commitment to correctness but like [XKCD 1172](https://xkcd.com/1172/) ... the user is clearly in the wrong at this point.

account4212• 1 month ago

It's OK to reject technically valid emails that will only be used by RFC nerds trying to prove a point.

chrisandchris• 1 month ago

It turns out that allowing senders to omit dots is common but by no means universal!

I think this is mostly common with Gmail-heavy countries and does not apply to Europe? At least I do not know of anyone that thinks so.

mmh0000• 1 month ago

https://fightingforalostcause.net/content/misc/2006/compare-...

This is one of my favorite articles on validating emails using RegEx, I fondly remember reading it over 15 years ago. It's stuck with me ever since.

SeanLuke• 1 month ago

These are waaay too complicated. Web developers can't even handle the easy stuff. My email address is of the form sean@foo.bar.baz, and email address validators on websites reject my address about 30% of the time because it has two periods.

christophilus• 1 month ago

Honestly, I just validate that it has an @ and then let it through. The actual sender (mailgun, or whatever) can do the dirty work for me.

Joker_vD3• 1 month ago

    \.{1,100}@\.{1,100}

I'd probably also have a red warning line under the input field for something really fishy and also most common typos (like "gmail.con") but other than that, I'd let it through.

davchana• 1 month ago

Discover bank, refuses to accept name@sub.example.in, but happily accepted name@example.us

davidw• 1 month ago

[Old man voice] Back in my day these kinds of articles loved pointing out that, well, the email address could be a UUCP address and that's a whole different parsing situation.

Of course, even then in the mid 90ies, UUCP was not something one really encountered outside of "so you think you're going to parse an email address with regexp?!" articles.

https://en.wikipedia.org/wiki/UUCP#Mail_routing

mesrik2• 1 month ago

Oh, and there were more than just UUCP bang paths.

IBM Memo, Novel Netware etc. groupware and such X.400 and routing those required also odd email conventions. VAX VMS addresses did have % left side routing in too.

smelendez• 1 month ago

Another one is that you can tell “professional” from “personal” email addresses or that every address even cleanly fits into just one category.

A lot of small business owners use gmail or a longstanding ISP account. A lot of people have personal email addresses you can’t easily distinguish from professional ones, between college alumni addresses, personal domains, and obscure ISP and email providers that aren’t in your database.

TZubiri2• 1 month ago

Soooo, let's just send a validation email and if they confirm the code, then it's a valid email?

Functionally there's no false positives or false negatives

AndroTux4• 1 month ago

There's a lot of false negatives because emails get stuck for hours, get blocked by the spam filter or fail to be delivered for whatever reasons.

atoav2• 1 month ago

I think most of these issues are easy to resolve by being more permissive and supporting what the technical standard allows for.

The Big Problem™ however is case sensitivity in the local-part, because there multiple incompatible things collide:

1. Users are not universally aware of case (in)sensitivity in one direction or the other

2. Existing systems may or may not interpret case at all

My preferred solution would be to adjust the standard to ignore case in the local part by forcing it to lowercase. That aligns with most of the systems and mental model of technically proficient users anyways. It makes much more sense from an UX standpoint since the goal is to be imambiguous.

If we were to enforce the opposite: case sensitivity in the local part this would have multiple downsides:

1. It is inconsistent with itself by making the local part case sensitive but the host part not, that is harder to explain

2. You have to train users to be precise about case on entry. As someone who worked in IT-support, this is a very bad idea. This includes second-order issues like phishing attacks by silbling emails where just the case differs

3. If your service stores email addresses it will need to know whether that specific Mailserver/client/etc treats the email as case-sensitive or not

In my eyes email servers that allow case sensitive local-parts are functionally broken, even if they don't break any rules.

account4212• 1 month ago

There are two parts where the case (in)sensitive distinction matters:

- what case you use to send mails

- what rules you use to determine if two email strings are the same user

For the first you can and should always use the address exactly as entered. For the second that's going to be a guess anyway and the exact rules depend on what false positives and false negatives mean for your use case - and you are going to have at least one of those two. Assuming case insensitivity here is generally reasonable for most use cases.

atoav2• 1 month ago

One thing I have learned about verification is:

Don't just put a link into your mail that directly verifies an email when visited. At least put some button or code input field there.

Why? There are mail clients that will automatically open links for users and if that link is now invalid the user is confused about being able to click them.

greengreengrass6• 1 month ago

Or, even easier, just make the call idempotent. The user doesn’t know anything and doesn’t have extra clicks, and it doesn’t matter much if the mail client actually did the “confirming” given it’s proven the email address is valid at that point.

The token was recently used? No problem! Must be a duplicate click, or a refresh, or the user left the browser tab open and their mobile device refreshed when they reopened the browser app, etc.

Dylan16807• 1 month ago

You don't send confirmation links just to prove the address is valid.

Ekaros• 1 month ago

Also much more critically. Just because mail is successfully delivered does not mean it is in the right inbox. So just link being visited by automation is far from enough in confirming that right person received the mail.

p0w3n3d• 1 month ago

You really did -- in your domain name, didn't you?

ramon156• 1 month ago

I wonder if bot traffic is less if an emdash is included.

croes• 1 month ago

And even if you know that an email address is perfectly valid it still could be simply wrong because of a tpyo.

julian_t• 1 month ago

"Email addresses always have a 'normal' TLD"

I registered a ".consulting" domain for my little company when they became available, and it has proved highly problematic ever since. Strangely (or perhaps not) it seems to be the larger players that have the most problems. I would at lest have expected ISPs and comms companies to keep up with this (looking at you, Three)

dijit• 1 month ago

I once worked for a company that had a .company gTLD but not the .com

It was also a bloody nuisance. Spam filters were one thing but there were so many validation forms that failed.

Every reasonable variation of the company name as a .com/.net/.org was taken, including <companyname>company.com

Ugh, what a nightmare.

Domain holders are the landed gentry of tomorrow if we keep this up.

merelysounds• 1 month ago

Every reasonable variation of the company name as a .com/.net/.org was taken, including <companyname>company.com

Even then it seems better to come up with a different prefix, or suffix (or both!), just to stay with ‘.com’.

Of course hindsight is 20/20 and I did the same, my personal homepage used to have a ‘.xyz’ address.

account4212• 1 month ago

Every reasonable variation of the company name as a .com/.net/.org was taken, including <companyname>company.com

That also means that customers WILL confuse your company with others in non-domain contexts so perhaps it's a good idea to choose a more unique company name.

thih9• 1 month ago

Another anecdote, I no longer use my ‘.email’ email address for the same reason.

KurSix4• 1 month ago

The annoying bit is that owning a domain should make email feel more stable and professional

account4212• 1 month ago

While on the sending site you should accept any domain, it's IMO irresponsible to use nuTLDs for pretty much anything as they are privately owned and you have zero recourse when the owner decides to change the deal on you.

frereubu• 1 month ago

We have a UK client in the healthcare industry who registered the domain clientname.healthcare, and they rapidly found that the NHS imposed regexes which rejected name@clientname.healthcare emails.

Aside from regexes though, I also think the new TLDs confuse quite a lot of people. name@clientname.healthcare just doesn't click as an email address as quickly as name@clientname.com, and I'm in tech so I'm sure it's much more confusing for people outside that space.

In fact, that reminds me that we built a site for another client for use inside an exhibition space which was spacename.house and against our advice they put that - without www or https:// - on exhibition panels for use on mobile phones. I am absolutely convinced that most people didn't realise it was a web address.

croisillon• 1 month ago

the domain name of my former employer was 18 digits long and i had to login in 10 services a day with it, it was a bit horrible

having a 10 digits tld is self-harming

clan• 1 month ago

I have noticed many non-techies simply put words into the address bar and click on the first link from the search result.

So if people just remembers spacename.house then that might be enough.

My dad tend to skip the TLD part as well. The results usually work. When they do not - he gets very confused.

The Internet is really a gold rush for scammers.

connorgurney• 1 month ago

I did similar several years ago with the .services TLD. Lo-and-behold, I bought the .com not long afterwards!

dspillett• 1 month ago

rejected name@clientname.healthcare emails

For years I've had a catch-all subdomain to give out addresses like company@sub.domain.tld which makes filtering out the junk when companies invariably sell their email lists or get hacked much easier. It is getting rarer, but I still occasionally run into sign-on forms that don't allow more than one “.” after the @ unless it is due to a recognised two-part country suffix like .co.uk.

I would never use something that isn't a country TLD for email for this reason, I assume there are a lot of bad systems out there that will incorrectly see them as incorrect.

Freak_NL2• 1 month ago

This all old hat, unfortunately, and also a thing which will be gotten wrong by developers for years to come. Just shouting 'give me a regex for validating email addresses' will make an LLM like ChatGPT happily output bullshit suggesting some overlong regex which is flawed precisely as outlined by the linked article, even though no one is arguing for those long unmaintainable regexes once they've seen the light.

Ah well.

Where there is still room for improvement is in how email addresses are often made a little bit anonymous by a lot of websites. Did you ever see something like 'j*h@gmail.com'? Oh wow, that neatly leaves out John Smith's full name! Like showing only the last four numbers of an IBAN or credit card.

Except for us edge cases with a personal domain, where I then get 'm*l@myfullname.nl'. So stop that. Store it next to the bit of knowledge about validating email addresses — the bits of knowledge you use to correct junior developers and senior idiots.

KurSix4• 1 month ago

This is a nice sibling problem to validation. In both cases, the bug is assuming an email address has a predictable human structure

FinnKuhn2• 1 month ago

I just tried this with Claude Opus 4.8 and I think it don't see any of those issues:

The first sentence is that there is no single regex that perfectly validates every technically valid email address. I think that is a good start.

It then recommends the regex used for <input type="email"> and explains that this would cover the majority of email addresses used by actual people. It also shows an improved regex that handles dot-atom local parts, quoted strings, domain names, and IPv4 domain literals, but doesn't cover things such as comments, full IPv6 literals, or internationalized addresses.

It ends with the only correct advice (in my optionion): Send a confirmation email.

Freak_NL2• 1 month ago

Does it say 'don't bother with a regex beyond checking it contains an @ surrounded by arbitrary pieces of text?' This still sounds like it is leading developers to conclude that they should use a too complex regex and then send a confirmation email.

Claude Sonnet says:

A practical email regex that covers the vast majority of real-world addresses: > ^[a-zA-Z0-9._%+\-]+@[a-zA-Z0-9.\-]+\.[a-zA-Z]{2,}$

Which is still way more complex than needed (and takes effort to read), and buggy according to years of blog posts written about this topic.

Of course the problem is the developer asking for a regex at all, but the must-regex-email instinct seems heavily engrained in our collective psyche.

I have no idea what other pay-to-play models say.

dvh• 1 month ago

It's not lies. And it's not about me either. If I collect email address, it will be used somewhere, someday, in god knows what app. If I'm the one collecting the email, I will make it as restrictive at possible so that it doesn't causes issues down the line. If it's too different than John.Doe_123@example.com, it's best to reject it.

For robust systems the goal was never to allow user type any technically valid email. It is to allow only emails that will not cause issues in the future.

KurSix4• 1 month ago

Email addresses are a great example of boring infrastructure hiding decades of edge cases

rock_artist2• 1 month ago

In that sense, it’s actually pretty surprising that so much of the world’s population wasn’t able to put their own name, in its native written form, in an email address until just 14 years ago.

Maybe for some internal usages. but imagine someone from a country using different language and characters gives me a card with their email. It's now far less portable for me to use it. Those days, I surely could picture it and find the email most likely getting it right.

But email as means of international communication, like passport, should be readable as possible or it kills its purpose.

Even with ASCII emails I have, I already sometimes struggle to pass them over phone or other methods :)

account4212• 1 month ago

Agreed, (a subset of) ASCII as the lingua franca of identifies is very useful. Almost all languages managed pretty well with ASCII-encodings of their special characters even if some individuals choose to be offended.

mitxela2• 1 month ago

What if the agreed upon international standard alphabet didn't happen to be the one you natively write with? If the world agreed to write all email addresses in katakana, that would work just as well as ASCII, right? I have to ask this because a lot of people confuse "single international character set" with "single international character set that happens to be my one." If you'd also be okay with katakana, then you're consistent.

rock_artist2• 1 month ago

English nor Latin characters are my native language. My language is also written from right-to-left.

So if it was broadly used and what charset used by a reasonable amount of the population then yeah I’d of course learn it in early age as I had to learn English.

swampangel• 1 month ago

Maybe for some internal usages. but imagine someone from a country using different language and characters gives me a card with their email. It's now far less portable for me to use it. Those days, I surely could picture it and find the email most likely getting it right.

It would be more portable for use with their peers who speak the same language, rather than requiring that everyone they want to communicate with in their own language and alphabet understands a second alphabet just for the addressing scheme.

account4212• 1 month ago

It is relatively expensive to run

Compared to sending a mail or to a customer not getting a mail they wanted?

Try to keep it as non-restrictive as possible. Something like ^[^@]+@[^@\s]+$, which only makes sure your user has input “something@something”

Requiring a dot in the domain part is perfectly valid. It makes no sense to not validate that the address is in a format that you can actually send something to, which include a domain that you can look up and isn't specifically rejected by your MTA.

This belief will probably be more commonly held in the English-speaking world, but I’m curious: If you’re not in the Anglosphere, do you still expect emails to require ASCII latin characters?

Yes, I do not trust Unicode with all its ambiguities and alternate forms to resolve to the same identifier on your and that I intended. ASCII-only email addresses are the norm everywhere I have seen.

artistonn• 1 month ago

It is relatively expensive to run

yeah, that is a pretty bizarre claim, as if millions of accounts are created per second

frankly this claim makes me think this article is LLM generated, because while the claim is technically correct, it's not a real concern

echoangle• 1 month ago

Maybe I'm taking this too lightly but honestly, if you're playing games with your email address and then don't get my verification mail, it's kind of a you problem. If your email address contains non-printable unicode characters or an IP address as the domain part, I don't really care enough to add support just for you. And surely everyone who does this has a "normal" email as a fallback anyways.

forgetfreeman2• 1 month ago

"Regex is hard, regex wizardry is rare, and regex engine implementations are inconsistent. It’s very, very easy to accidentally get it wrong without realizing it."

The what now? I'm struggling to take this seriously because a decade ago regex where common knowledge, like if you don't have a handle on this you should probably go get a job in marketing levels of common knowledge. Has the profession fallen off this far in ten years?

naishoya• 1 month ago

Sad truth: Yes.

Yes, it has fallen off this far in the last ten years.

If you look a little further back, say to 2006-ish it's far worse than that.

Back then there were 'bright' middle-school ROV team members writing C and Ada+Spark for Arduino-board control-by-wire small craft to perform simulated ocean sample collection and tool manipulation tasks and winning in the unlimited class against university competition at international championships.

Now the "Profession" consists of teams using ChatGPT to cheat on basic coding tasks and "make nudify" of famous people from their work machines.

forgetfreeman2• 1 month ago

What the actual fuck. It's not like we're talking about sed/awk fuckery or manual memory management. Regex syntax is a basic programming concept that is natively supported in most languages. Next you'll tell me these incompetents can't normalize database tables...

greengreengrass6• 1 month ago

I, too, get so frustrated by + addresses not working that I’ve configured my MDA to rewrite —- (double hyphen) to plus, and use this in spite on sites that dislike the + variant. I’ve made it impossible to /not/ host my own mail delivery infrastructure now if I want every address I’ve ever given out to still work.

Although more recently I’ve moved to a catch all domain for throwaway, which is even better. It confuses agents on the phone though when I give my email address as {their company name}@mydomain.com

Yeah, most people don’t understand how the ownership and control varies before and after the @ symbol.

giancarlostoro• 1 month ago

Been wanting to do something similar my only hang up is coming up with a domain they wont butcher. When I got my passport I guess it must be OCR but they butchered my email completely.

kgwxd• 1 month ago

as {their company name}@mydomain.com

People are still doing that? To prevent spam? To "catch" the company leaking/selling your address? Now the spammers know they can likely use anything@domain, and it'll get to your eyeballs in some capacity. Also, companies have no shame anymore, they don't care if you know.

volemo• 1 month ago

But the portion of us is so negligible that it’s not worth for the spammers to handle our edge case. :D

scottmcmac• 1 month ago

Yeah, I do the same, but without the catchall for exactly that reason. If I start getting spam, the e-mail gets disabled.

kurttheviking• 1 month ago

I do but mostly for coordination and comms sharing with my spouse by using group aliases. Summer camp registration, school nurse contact info, car insurance, library holds...all super convenient to get joint notifications for things. And yeah, also to remember who we gave contact info to which we can drop if it gets spammy.

greengreengrass6• 1 month ago

I started doing it when so many sites had broken + aliasing stuff, which I use for filing mail to keep my inbox manageable and actionable, as it was easier to type than my double-hyphen hack described above.

I’m not concerned about the leaking as my address is out there anyway and Bayesian spam filtering is still decent enough, but as an aside, I have had two companies this year whose user databases must have been leaked on the basis of spam received at company-specific addresses. I reported it to their privacy people and pointed out it’s highly unlikely this “spam” originated as their (tiny company name) being chosen by chance by a spammer who figured out my catch all domain.

They never replied, and I probably should have followed up with the local information regulatory commission in each case. Hopefully, my note helped them identify they had a leak and to secure their systems.

garaetjjte• 1 month ago

In practice they don't do that, apart from spamming few addresses like office@ or accounting@. If some address starts getting spam I reject everything sent to it. For addresses that are getting spam but needs to be public (like contact addresses on website) I do more aggressive filtering (eg. I noticed that enforcing that recipient is actually present in To/Cc header cuts down a lot of spam).

dredmorbius• 1 month ago

The practice also makes filtering more effective.

Rather than whitelisting simply on a given sender, you can rely on both the sender and the recipient address matching a known list. This needn't be a single sender address. If you have multiple contacts at a domain, or a given entity relies on several email services (e.g., direct personal email, vendor-based marketing emails, vendor-based support or notification services), you could add all of these to the "from" match set.

I'm thinking through phone comms presently and am considering a similar concept for mitigating ever-growing phone abuse. Running a VOIP/PBX system, having multiple internal, non-public "extensions", each of which is valid for only a small subset of caller numbers. The "extension" space could be large (6--9 digits, say, millons to billions of values), making exhaustive search / coincidental match infeasible.

(This is only one of a few approaches I'm thinking of, it happens to resemble the specific email practice being discussed.)

gonzalohm• 1 month ago

How do you deal with sending emails? When I was self hosting my emails would be flagged by Gmail (or any other email providers) so I effectively only had a self hosted inbox, which sucks

picofarad3• 1 month ago

Dont use a random IP to host? I use fastmail, even though they're trying to convince me that I need to pay ~$45 now instead of $5/year.

And they sent me an email explaining how grateful I should be, that I'm grandfathered in to being able to use my own domain on a "plan" they dont even offer., in a plan that didn't offer custom domains.

Well how'd I get all that then? I signed up for fastmail explicitly because $5/yr for custom domains.

Anyhow if you pay a host you're probably fine. Or find someone with an old /24 thats had a /31 or /32 unused for a long while, and no other black marks against the /24. And use that IP, set up demarc and all the other new email DNS stuff.

greengreengrass6• 1 month ago

My setup is more complicated than it needs to be for $reasons (I like playing with networking protocols, have my own v6 prefix and ASN etc. and my mail and other important personal services are hosted across multiple sites for redundancy), but any competent VPS host that offers you a static IP - coupled with some DKIM, SPF and DMARC configuration that will take an afternoon - should solve the problem. I rarely touch my home setup and it works fine; mail doesn’t go to reputation black holes and it’s been like this (literally) for decades. I invest in architectural tweaks and improvements perhaps every 5 years.

I do run similar infrastructure professionally for a living, which probably helps with getting it right first time. Competent VPS hosts care about IP reputation for mail; e.g. Hetzner only allows outbound port 25 for “trusted” customers, which somewhat helps with abuse reports. Some hosting providers may even let you relay via their own outbound hosts if you have a VPS with them, which simplifies the operational aspect.

I rarely need to send from the catch all address, but Postfix can easily be configured to allow my user to send from other addresses, and then it’s just a case of adding as an alias in your mail user agent.

mrighele• 1 month ago

Not OP, but I self host a few domains.

I was worried about not being able to send emails, but is seems that as long as you setup properly SPF/DKIM/DMARC you're fine. You may have problems if using a domestic address though.

For the configuration, the best bet is probably to use a product that makes it easy to configure the above three, there are a few alternatives around, like Stalwart [1] or docker-mailserver (which is little more that your postfix/dovecot/rspam combo packaged in a container) [2]

[1] https://github.com/stalwartlabs/stalwart

[2] https://github.com/docker-mailserver

picofarad3• 1 month ago

What's the most common thing you hear when you do this? Usually its nothing, but the second most common thing is: "no, sir, your email address."

It gives me the fuzzies every time to explain I own the domain, and every email address on it is mine.

Since I have it on my phone, I can usually receive the email that they send very quickly and prove that everything's working fine.

I am wondering how hard it is to do this again today with a new domain though.

greengreengrass6• 1 month ago

The best one was when someone said they were going to give me excellent service because “you work for corporate”, confusing the company name before vs. after the @ sign. I forget which company it was now but the agent was convinced I must be someone important.

I was torn between explaining and letting them believe it :-)

Most of the time, folks just don’t understand why their company name is in the address and they think it’s a mistake.

To be honest, I do tend to avoid this for anything other than throwaways because it causes too much confusion when I have to phone up, and I’m not really doing it out of a misguided belief it helps with spam (at least, it doesn’t help any more than security by obscurity is unsuitable as a singular defence, but maybe has a tiny role when layered into a broader strategy…)

yencabulator• 1 month ago

I've found I can decrease confusion a little by using

  from.{their company name}@mydomain.com

and when I care about making it more phish-proof, I can go for e.g.

  from.{their company name}.{some numbers}@mydomain.com

sylware• 1 month ago

Many email servers do forget about the email adresses with IP literals, that for people who are self-hosted without paying for DNS.

mailbox@[x.x.x.x] and mailbox@[ipv6:...] (and probably without "ipv6" prefix once ipv4 is gone).

This is stronger than SPF since the second the IP of the sending SMTP server does not match the IP in the "from" headers and the envelope, the email is dropped, not even going into spam.

For instance, currently, if I send an email to a gmail slave, their parsers will ask for... a DNS PTR record, Oo "Geniuses" at work, or conveniently breaking all interop with small tech?

mesrik2• 1 month ago

There is one more 'lie' missing and not included in that writing which only looks email addresses what is are limits of valid destination addresses.

But if used as a senders source address there are even less limits.

For example you can use a null address <> when sending. That has been used bit less these days than earlier. It's been used ages SMTP delivery status notifications, mail loop prevention and so where intentionally not much sense to expect anyone to reply. And all well known MTA's forward it and email clients handle it very well by disabling reply to that message.

There is however a catch that anyone who thinks he would now start using it when he doesn't want any reply. Ever since IT Service Management (ITSM) and Service Desk software appeared, they have had issues with email coming from <> sender, because they like to always add received messages email addresses to database, where then someone handling would reply. I've been using only few, Service Now (SN) more lately and before Issue Tracker (IT), both didn't at least about year and half ago know how to handle null sender addresses. Both seemed to just discard or sort some trash bin those emails. With our SN sysadmin didn't find where those went in that system.

But otherwise <> as a sender works great. And sure it would be great if those ITSM making folks would get this fixed, because when your postmaster, postmaster, etc. and such role-aliases are the quite often handled by ITSM software, there is good chance you don't get some important notifications from systems that rely on that null address sender.

ps. Search Google: smtp and sender address as "<>" for more info incase needed.

jrrv• 1 month ago

In the year of our lord 2026, you can reasonably expect your users to know how to type their own email address

Lies we tell ourselves about users.

UltraSane• 1 month ago

I own a domain I use for email and I have it configured to deliver ANY address that ends with @mydomain. This works like + addressing on steroids. I can have website@mydomain or recipient@mydomainand it makes filtering much easier.

alkonaut• 1 month ago

Validation to avoid mistakes is, as they point out, good. I'd even go so far as to extend it so that I reject those without any tld (without any dots) just because it's 99.999% a mistake and I don't care about the person who has ben@net. I'd also reject ip numbers.

Next is the spicy take: I need to consider WHY I am gathering this email?

If I'm gathering it for "marketing purposes" or any such cross correlation to other systems, then I'd also reject bob.smith+dontspamme@gmail.com. Or I'd keep both so you can do cross referencing on both the + address and the "raw" one.

dathinab3• 1 month ago

Punycode [...] and the local-part was still limited to ASCII.

the funny part is this is only half true

The true part: Punycode has never be standardized for the localpart and as such taking a email address with non us-ascii characters in the local part and punycode encoding it is fundamentally wrong.

But: Nothing prevents you to have a local part which "happens" to look like punycode and especially in the early SMTPUTF8 days many providers which did allow non-us-ascii email local parts automatically created an "alias" email address where the local part was punycode encoded. Nothing in the standard prevents this and as consequence punycode encoding a local part _might_ just happen to work for some subset of non-us-ascii emails.

Const-me• 1 month ago

Good article. Worth noting C# standard library handles most of that complexity, no regular expressions required. Call System.Net.Mail.MailAddress.TryCreate, if successful read Address property to find the normalised address.

dathinab3• 1 month ago

Note: I have struggled to verify this one, and it’s possible I’m actually misreading the RFC.

Is correct, you can have quoted local parts and (I guess?) theoretically "foo"@mail and foo@mail should even be treated the same.

But practically this is a dead feature and probably should be treated as non existing.

AFIK `[<ip-address]` mails are used by some old data centers for delivering automatic generated "error" mails from unix server in a way which doesn't break when DNS is down.

Also interestingly the `[..]` syntax has a generic extension hook, and that hook allows usage of @ characters. So technically a `foo@[custom:@@@@@@@@]` is a valid mail address, just no one knows how to deliver it ;). (And `custom` must be registered with IANA, theoretically).

mjmas• 1 month ago

From my reading through the RFCs a few months ago the message and smtp envelope also have different rules for addresses, and the message allows the local-part to contain whitespace but the envelope doesn't.

dathinab3• 1 month ago

both allow it but only if you use quoted text AFIK

through the message does allow an additional display name (like `display name <email>`) which has it's own rules.

ale42• 1 month ago

An e-mail address can have multiple @ also for... source routing. Of course it doesn't make any sense nowadays, but it's technically allowed. RFC 5321 gives an example:

  @hosta.int,@jkl.org:userc@d.bar.org

This is a valid e-mail address, with source-routing along two intermediate servers. I guess no sane server on the Internet will accept this, but you never know... (this said, I remember attempting this around 1996, when many servers were open relays, and the message was happily delivered after passing through 3-4 servers).

tracker12• 1 month ago

I have a relatively good email address, and more than a handful of people who don't seem to understand email, just use my address... I've had payment confirmations from mlb.com orders, to tractor supply receipts and junk mail, to student loan paperwork. It's amazing how much garbage I see all because nobody actually confirms email address ownership before signing people up for crap.

The worst is some foreign gambling site, I can't even log into to change the preferences and cancel the account.

Though, I did deface then delete someone's dating profile once, who signed up on an app with my email...

Lies we tell ourselves about email addresses

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