Outlook New and Classic have deeply inconsistent and inefficient UIs

I have nine appointments in Outlook for which I want to set the category and the status (e.g., to “out of office”). Unlike the Apple Calendar, there is no way to select multiple appointments in the calendar. So, I searched for the appointments. In New Outlook, it shows the elements in a list on the left-hand side. So far, so good.

I cannot multi-select the search results, though. Nor can I apply any operations on an individual search result. The search items are just inert and only serve to highlight the entry in the calendar view.

New Outlook doesn't let you do anything with search results − no multi-select and no operations

Lemme try with Classic Outlook. I can search for the items and I can multi-select them. So far, so good!

Outlook Classic shows a multi-select list for results

However, I can only change the category, not the status.

While you can categorize in batches, you can't set the OOO status

Even when I did set the category for all nine appointments in Classic Outlook, New Outlook only picked up about half of those changes, seemingly arbitrarily. Even minutes later, it had still not synced, so I just gave up and set the category again, manually.

This is almost too minor a task for which to bother building a prompt for Copilot (or, most likely, a few prompts), so I just did it manually. But these shoddy and inconsistent UIs that fail to deliver orthogonal features that work everywhere are the reason that LLM-based “enhancements” like Copilot are so popular right now.

Instead of actually building a usable UI once, you force the job on your users to constantly recraft prompts to do things in your program that your design and implementation teams should have done for them. Instead of a building a well-implemented, consistent, and well-documented feature once, we boil the oceans and burn down the rain-forests to have an LLM-based tool reinvent a pale shadow of the feature again and again and again. This is madness.

In this case, I have to give Apple kudos: their calendar reminders are a dumpster fire but at least the calendar—even the version in MacOS Monterey on my old iMac—allows me to multi-select appointments over several months and switch the calendar to which they are assigned. The iCloud view and calendar on a much more modern MacOS on my laptop updated nearly instantly (delay of only a second or two).