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I can confirm
(lemmy.dbzer0.com)
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this post was submitted on 20 Mar 2026
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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.