Amost all mail clients nowadays have the feature, that if you write something like "File" or "attachement" in your mail, and you dont have anything attached, it asks if thats correct.
But yeah, that happens all
this post was submitted on 10 Jan 2026
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The first thing I do when emailing an attachment is to attach it.
Then I write and review my email.
The last thing I do is fill out the To field, that way I don't accidentally send it before it's done or send it before reviewing fully.
My trick is to start by adding "don't send" in the BCC line of every email first thing. Then only remove it after writing and double checking everything.
If you try to send it before removing the "don't send" text, Outlook will show a prompt that it doesn't recognize the email address and will ask you to confirm before sending.
One of the only "AI" features that I've ever actually found useful was the thing that warned me when I sent an email that was missing an attachment. Basically, it was able to deduce that an attachment was likely missing, and showed me a "are you sure you want to send" prompt.
You don't need AI to check for "Attached"
That is true. You can have check for certain words and phrases that's hardcoded in. However, I have reason to believe the feature I experienced was using an LLM rather than a hardcoded list of search patterns.
I remember Google doing it years ago before LLMs were big things.
Mozilla Thunderbird, too. Saved me so many times.
This is an old feature, it existed long before LLMs. Nothing needs to be hard coded, machine learning is/was advanced enough to do it already.
That was before AI.
The real meaningful use for AI is for things like this.
In Outlook, they're keyword-based. Use words like "attached" or "file" and it will automatically prompt you, regardless of the context.
Of course, I'm sure Microsoft is going to cram copilot into it, so that it stops working sometimes
Forgetting an attachment is pretty easy to fix though. You just reply all right away and say oops forgot attachment and attach it.
The problem is when you have some typo down in the middle of the email. No way to fix that. You can’t reply all and say ”oops I meant ‘disk message’ not ‘dick massage’” because people already knew it was a typo anyway, but then you’re so neurotic that you felt the need to let everyone else know that the typo bothered you so much that you had to send another email about it, rather than just moving on with your life.
Order of operations:
-
Start new email
-
Add desired attachments
-
Add title
-
Write the actual message in the body
-
Select recipients
-
Double check above in the same order
-
Send
Feels backwards, but you'll never fuck it up again.
attach before writing
It's not stupidity. Don't be so hard on yourself.
Then you gotta send a second email with something like “It would help if I attached the file haha” in the body.
but only attach the file on the third email
Just gotta resign at that point.