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
the_time.pdf

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.
Order of operations:
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Start new email
-
Add desired attachments
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Add title
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Write the actual message in the body
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Select recipients
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Double check above in the same order
-
Send
Feels backwards, but you’ll never fuck it up again.
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attach before writing
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.
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.
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
That was before AI.
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.




