Outlook search is so shitty that I am that guy.
“Why didn’t you send this email!”
They forward it to me again.
Now it shows in Outlook’s search when before I had performed a search with the exact subject line and Outlook couldn’t fucking find it.
It is so terrible. My job gave us AI agents that supposedly can search my email better.
Did MS purposefully enshittify built in features to make AI look better?
So the lesson here is to be less aggressive in your wording.
“Did you send that e-mail at (requested point in time)? I didn’t see it”
“Could you tell me the title of that e-mail? My Outlook isn’t finding it”
“Could you resend that e-mail? I think my Outlook is having issues”
Be sure to click on Inbox before performing searches, as otherwise they’ll be limited to whatever folder you’re in.
I will usually call myself out.
I will say “I thought you sent me the email but I just can’t find it, I’m so sorry, would you please send it again.”
I hate it and hate not being able to find info when I need it.
How is Microsoft worse at this kind of thing after all these years of making productivity software?
Could it be their vibe coded AI slop of a platform?
Yeah searching email has been a solved problem since like 2000. Probably even earlier than that. So if it’s broken now, it’s on purpose.
“As per my previous email [bitch]”
If you truly forgot to send it, you can also retain the same effect by
- creating the reply email
- save it as draft
- goto your draft folder
- click the draft and choose to forward it
- the new email forward will look just like it normally would except the headers will have the current date and time, modify as necessary
- add appropriate told-you-so text to the body of the forward and highlights in the “original”
problem solved.
That’s why the message-id from the cc so you can ask them to check with their mail admins (or shut up, Karen) is golden.
The letter is nothing. The envelope is holy and mighty.
Even better when you get to mark specific points in that email with highlighter tool. “Look, this and this is what you missed because you can’t be arsed to read”
