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Comment by ubermonkey | Hacker News Reader

We are a small software company.

We use Office 365 and their hosted Exchange for email. I manage my mail in the native Mac Mail tool; my boss uses Outlook. For commercial exchanges (ie, dialog about sales with customers), we're almost always both on copy.

SEVERAL TIMES A MONTH he asks me to find a mail for him, because Outlook search is letting him down, often on bone simple searches (e.g., for something like a specific PO number or software serial number).

I find it immediately. Outlook strikes out. How do you break search so badly?

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Yeah it's because Mac Mail downloads every single email and indexes it locally. Outlook (especially the new one) is just electron-based webmail. So every search happens in the cloud and it doesn't have a full copy of all your emails.

This would not be a problem for searching of course, if the cloud-based search worked properly. But yeah... About that. :X

The "classic" outlook should do it better but it also doesn't in my experience. Though I can't use it anymore at work lately.

It's just so bad because how can they screw this up? It's not some fluff feature, it's a core feature in an email client.

PS: If you have copilot, it does a lot better at finding stuff somehow, though like every AI it can be a bit hit and miss.

AI in search is just evil, something either exists or it doesn't, maybe on a Tuesday isn't good enough.

Well I have mixed feelings about it.

For general searches, I agree. I want those to be highly deterministic. But in that case I need to know exactly what I'm looking for.

There's also the other kind of thing though. "Who was that guy that I emailed with a year or two ago about this issue with MacBook Enrolment?". Yes I can filter by company or other details if I remember those things but sometimes I don't. And that's when AI search can really shine. Or not, it can also totally make up stuff out of its ass. But at least when it comes to emails that's easily verifiable.

I can see the usefulness.

But I'm already sick and tired of search not returning stuff I know is in there, because I forgot to check the blessed combination of boxes.

He's running full Outlook, not the shitty new one. And anyway this problem has existed for 10 years.

At that point i would switch to thunderbird or something

It's really a PITA to use standard protocols on M365 now though. They try to make it as difficult as possible. And you need lots of exceptions from your admins. Everything is "legacy", the Microsoft word for Not Invented Here and they make it sound like something super dangerous.

Of course that third party clients don't give them any telemetry, "insights", cross-marketing opportunities like copilot, has nothing to do with it.

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