January 2025 for a tax receipt; if you count deleted emails saved locally, probably a legal matter-related email in 2023. I delete almost everything as long as they are no longer useful so…

First week of May, 1990. Welcome email to my first job on a university campus. I exported to an mbox file and can still access with Thunderbird. I have every email since. It’s… a lot.

Nov 2003

From 2011 a comic strip emailed to me by a friend.

If I exclude SMART status reports then the oldest one is from 2023-08-21 and is sitting in the trash. If I exclude trash then 2025-07-30 from my mom.

I usually deal with emails immediatelly and then delete them completely (not sending them to a trash).

When you realise this is a recovery question to your email account 👀

I’ve got one from Thu, 10 Mar 1994, but it’s boring and this one stands out more:

On Sat, 17 Feb 1996, Dolphin Satan wrote:

I can’t fuckin see your page man!You need to get rid of that white font.

Fuck you. Get some fucking glasses.

July 30, 2004.

An email from my dad.

I don’t delete emails unless they’re spam.

9/27/2004

1996 if you count print copies in a binder.

The earliest message I have accessible in Thunderbird is from the 25th of May, 2001. It’s part of a conversation with old work colleagues who I had remained drinking buddies with when I started a new job nearby. (There are actually two messages with earlier dates, but one is an imported message from March of 2001 that wasn’t actually sent or originally received by me, and another that’s an old Usenet post, probably also imported, that doesn’t have a datestamp at all, registering as 1/1/1970.)

If I go digging around in my university backup, I have messages from 1998 in there. I would have earlier e-mails, but quota was limited on the University systems, so I expect I deleted everything at the start of every year.

Probably some mail from 95. I never delete anything.

I had email going back to at least 1996 if not earlier, but my computer was stolen in 2004 during a move, and that was before the big switch from POP3 to IMAP.

Sept 7, 1993. It’s a college-oriented chain email that ends with “pass the beer” that a friend who’d just gone to college sent to about 30 people, which caused ancillary reply-all conversations for the next year or so.

Original welcome email on my Gmail October 2005.

Subject was “Gmail is different. Here’s what you need to know.”