Review: The new Outlook for Windows

Outlook is asking for my feedback. I went to the bother to type it up, so I'm posting it here as well to get as much mileage out of my effort as possible. I don't trust Microsoft in general to read feedback, but I think that the Outlook team does.

Likelihood to recommend: 1/5

Why?

The feedback

I am a programmer, not a suit. Outlook's strength is in coordinating meetings. My job doesn't require many meetings.

I have to use Outlook because my company does. The features I would look for in an email client:

• Plain-text email
• Markdown support
• HTML editing
• Keyboard-based navigation
• Scripting capabilities

I do appreciate that Outlook now allows me to check email headers.

I find Microsoft 365's Ctrl+Backspace behavior idiosyncratic and unhelpful--except that it works properly in this feedback box, which is nice.

I actively disable any sort of smart tooling, even spelling autocorrection, and definitely including Copilot. I don't use Copilot to draft emails because it would be simpler just to send the prompt. I don't use Copilot to summarize emails because I don't read emails that need summarized.

Outlook and Teams have all these buttons I will never use and care about, but I still get a reminder for a recurring meeting every day at the default time even though I changed the reminder time. The notification comes up fifteen minutes before the meeting. The little drop-down box says "10 minutes before", which is what I selected. It is most amusing.

The "Upload to OneDrive" button

1. I go to attach a file to an email.
2. The file is too big, so I drop it onto the button for "Upload to OneDrive and send link".
3. I send the email.
4. The recipient emails me back to tell me that he can't access the file at the link I sent.

What good is a link that the recipient can't access? If I am attempting to email a file, can we not assume that I wish the recipient to be able to read it? Why can't the "Upload to OneDrive" button make the file accessible by the recipient of the email? Or at least provide a quick way to do that?

I feel as though the assumption is that I will mostly send files to others within the company. But I do nearly all my internal communication through Teams. So if I send a file by email, then I am almost certainly sending it outside the organization.

(Unless I am sending a script that isn't in the Git repo. If I send new versions by Teams, then Teams will increment the file name of each version. This increment will include a space character, forcing the recipient either to rename the file after downloading it or to quote the file name when he types it into the terminal. So I might send the script by email to avoid having the file automatically renamed. But I digress.)

An Outlook bug gives me paranoia that Microsoft may be reading my feedback

If I must be a Shore Pibald, I might as well at least document it for learning.

Using the new Outlook rather against my will, I went to search the help articles for a basic feature it does not support, as one does.

This is suboptimal UX. So of course I left feedback, something like "Text is barely readable in Help search box in dark mode".

Immediately, I saw a change:

This is clearly better, if not particularly professional-looking, but why did it change so handily and abruptly?

I restarted my Outlook and searched Help again. The text field was back to the old appearance. (The first screenshot is from after the restart; I naturally had no reason to take one before.)

Obviously, Microsoft has an AI watching user feedback and making minor UI tweaks to increase customer satisfaction. But I can't even get an AI coding assistant that edits code inline, and if Microsoft had one, they would be selling it, so that explanation is clearly implausible. Or maybe an actual person is reading my feedback and making tweaks in response. [insert joke at Microsoft's expense]

But look what happens if I mouse over a suggestion of a recent search:

So apparently the suggestion mouseover code erroneously activated and coincidentally gave me just what I was asking for.

As David Malki notes, the human mind jumps first to implausible explanations.

I am relieved and vaguely disappointed.