Hi Tim,

> Turned out the local part of the email address was case sensitive. She
> had no idea this was the case, and it's the first time I've ever
> (knowlingly) encountered this. Looking at the email headers, they're
> using a Microsoft Exchange SMTP server. For the low-down:
>
> https://stackoverflow.com/questions/9807909/are-email-addresses-case-sensitive

I disagree with the final conclusion of the top-scoring answer there.
The case of the username part does matter.  :-)

It starts okay, explaining the why.  Email started within a machine.
The ‘address’ was just the username.  Usernames are case sensitive on
many systems, including Unix.

When passing email between machines was added, e.g. the routing path
eclipse!inputplus!ralph, the host at each hop deleted itself from the
start of the list and passed it on downstream.  The only interpretation
of the username part was by the final hop.  As DNS didn't exist, a table
of hostname to network address for the world was centrally maintained
and shared, called HOSTS, stored locally on Unix as /etc/hosts.  RFC 810
says hostnames are drawn from A-Z plus punctuation and never uses
lowercase, probably because some interfaces still couldn't render it at
the time.  Unix's preference for lowercase is probably why the hostname
look-up became implicitly case-insensitive.

Maintaining a worldwide /etc/hosts-equivalent was tedious and DNS was
born; it preserved the case-insensitivity.

Routing email explicitly was a nause and with DNS the switch to email
delivery with DNS A and MX records allowed just the
username@final.destination, but both halves maintained their original
semantics: case sensitive before the at-sign, insensitive afterwards.

Unix mail servers gradually started to handle non-Unix email senders on
other platforms failing to use the correct email address, e.g. Sendmail
has an F=u flag related to case-conversion.  By working around the
problem, they help propagate it.  Postel got it wrong.  :-)

I'm a customer of a financial institution that insists on sending emails
to capitalised addresses, e.g. freda.blo...@example.com.

-- 
Cheers, Ralph.

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