'Don't even consider' Microsoft? Gosh

"In fact, the subtitle is more descriptive: "In which a G-Suite user navigates the upside-down world of Exchange, 365, and SharePoint." It's a fascinating glimpse into how horrifyingly complex, even irrational, the Microsoft 365 software stack looks to someone who is used to the Gmail way of handling such business communications: groupware, as it was called in the ancient times. Email, user accounts, file sharing, and so on."

"There is no way to make your default view in Outlook put unread messages at the top. To obscuring rather than highlighting important information: By default if you decline a meeting invite, that meeting completely disappears from your calendar. Via entire concepts that should be long obsolete: Why is "Syncing" Outlook a thing? It's 2025. My email should be syncing automatically."

"The impression is not good. His criticisms are many, varied, and categorized: Outlook and Calendars, SharePoint and OneDrive, "Everything is an everything application," then Groups, and finally a conclusion. Significantly, that links to the excellent " PHP: a fractal of bad design" article from 2012, which we highly recommend to anyone not familiar with it. His gripes range from simple UI issues: There is no way to make your default view in Outlook put unread messages at the top."

Microsoft 365's components create convoluted workflows: Outlook, Exchange, SharePoint, OneDrive, and Groups produce overlapping, confusing interfaces and features. Default Outlook behaviors impede usability, such as inability to sort unread messages to the top and removal of declined meetings from calendars. Synchronization workflows remain manual in places, creating expectations mismatch around automatic email syncing. The calendar model differs from Gmail's approach, relying on email updates for meeting changes and enabling awkward scenarios like inviting others to meetings by forwarding invites. File sharing and group features intermix, producing redundant "everything" applications and compounded complexity for users accustomed to simpler G‑Suite patterns.

Read at Theregister