The problem with

14.03.2016 19:41

At this moment, the (note missing m) top-level domain is registered by Google. This is not surprising. It's common practice these days for owners of popular internet services to buy up domains that are similar to their own. It might be to fight phising attacks (e.g. type affairs), prevent typosquatting or purely for convenience to redirect users that mistyped the URL to the correct address.

$ whois
Registrant Organization:                     Google Inc.
Registrant City:                             Mountain View
Registrant State/Province:                   CA
Registrant Country:                          United States currently serves a plain 404 Not Found page on the HTTP port. Not really user friendly, but I guess it's good enough to prevent web-based phising attacks.

Now, with half of the world using email addresses, it's not uncommon to also mistakenly send an email to a address. Normally, if you mistype the domain part of the email address, your MTA will see the DNS resolve fail and you would immediately get either a SMTP error at the time of submission, or a bounced mail shortly after.

Unfortunately, domain actually exists, which means that MTAs will in fact attempt to deliver mail to it. There's no MX DNS record, however SMTP specifies that MTAs must in that case use the address in A or AAAA records for delivery. Those do exist (as they allow the previously mentioned HTTP error page to be served to a browser).

To further complicate the situation, the SMTP port 25 on IPs referenced by those A and AAAA records is blackholed. This means that a MTA will attempt to connect to it, hang while the remote host eats up SYN packets, and fail after the TCP handshake timeouts. A timeout looks to the MTA like an unresponsive mail server, which means it will continue to retry the delivery for a considerable amount of time. The RFC 5321 says that it should take at least 4-5 days before it gives up and sends a bounce:

Retries continue until the message is transmitted or the sender gives up; the give-up time generally needs to be at least 4-5 days. It MAY be appropriate to set a shorter maximum number of retries for non- delivery notifications and equivalent error messages than for standard messages. The parameters to the retry algorithm MUST be configurable.

In a nutshell, what all of this means is that if you make a typo and send a mail to, it will take around a week for you to receive any indication that your mail was not delivered. Needless to say, this is bad. Especially if the message you were sending was time critical in nature.

Update: Exim will warn you when a message has been delayed for more than 24 hours, so you'll likely notice this error before the default 6 day retry timeout. Still, it's annoying and not all MTAs are that friendly.

The lesson here is that, if you register your own typosquatting domains, do make sure that mail sent to them will be immediately bounced. One way is to simply set an invalid MX record (this is an immediate error for SMTP). You can also run a SMTP server that actively rejects all incoming mail (possibly with a friendly error message reminding the user of the mistyped address), but that requires some more effort.

As for this particular Google's blunder, a workaround is to put a special retry rule for in your MTA so that it gives up faster (e.g. see Exim's Retry configuration).

Posted by Tomaž | Categories: Life


Someone sent me an anonymous email with before .com. Will that damage my computer, and will it track me? What would be the reason for that? It was a rude, nasty email about another person. I tried to message the email address to someone on Facebook and got a message that it "violates community standards".

Posted by Linda

So, basically, emails can be sent to "" addresses but would be bounced back and not actually delivered. I accidentally typed in on my email to a friend, will I receive an error email back?

Posted by Esuba

Add a new comment

(No HTML tags allowed. Separate paragraphs with a blank line.)