Microsoft is uniquely unable to name / brand anything sensibly:

"Outlook" / "Outlook Web Access" / "Outlook Web App" / "Outlook.com" / "new Outlook for Windows" / "Outlook (classic)"

.NET: .NET Framework. ASP.NET. .NET Core. Windows .NET Server. Ugh...)

The love of the term "Explorer": "Internet Explorer" / "Windows Explorer" / "File Explorer" / "MSN Explorer"

Similarly is the love of "Defender": "Windows Defender" / "Microsoft Defender" / "Windows Defender Antivirus" / "Windows Firewall" / "Windows Defender Firewall" / "Microsoft AntiSpyware" / "Microsoft Security Essentials" / "System Center Endpoint Protection"

"Messenger" was a term they loved: "MSN Messenger" / "Windows Messenger" / "Windows Live Messenger" (which also evokes the whole "Windows Live" series of products)

Windows 95 shipped with an email client called "Exchange" that could be used peer-to-peer (using a filesystem-based "Microsoft Mail Postoffice"), but there was also the email server platform "Exchange"

"Microsoft Teams" / "New Microsoft Teams" / "Microsoft Teams for Business"

"Microsoft FrontPage" / "Site Server" / "Site Server Commerce Edition" / "Office Server" / "SharePoint Portal Server" / "Windows SharePoint Services" / "Microsoft Office SharePoint Server" / "SharePoint Foundation" / "SharePoint Server" / "SharePoint Standard" / "SharePoint Enterprise" / "SharePoint Online" / "SharePoint Designer"

"Office Communicator" / "Microsoft Lync" / "Skype for Business" / "Skype" / "Skype for Business Online" / "Skype for Business for Microsoft 365"

Fairly guffaw-inducing branding, to me, was removing the Remote Desktop Client app and introducing something called "Windows App".

The old "System Management Server" became "System Center" and its family of products.

There's the whole accounting software / ERP world, too:

"Great Plains" / "Dynamics GP" / "Navision" / "Dynamics NAV" / "Solomon" / "Dynamics SL" / "Axapta" / "Dynamics AX" / "Dynamics 365" / "Dynamics 365 for Finance and Operations" / "Dynamics 365 Business Central"

(For most guffaws induced, though, there's the Windows 98-era "Critical Update Notification Tool"[0])

[0] https://en.wikipedia.org/wiki/Windows_Update#Critical_Update...

How many products does Microsoft have named 'Copilot'?