Having worked with a client using Microsoft now, I feel ya. Logins are broken, exchange, admin, entra, everything feels so fragile.

Microsoft is a big place. I recommend focusing on the parts they do well rather than getting tribal. All of the following products and services are fantastic in 2026:

  Windows Server 
  SQL Server 
  .NET/C#/F#/Nuget
  Visual Studio [code]
  SSMS
  AAD/EntraID
  Defender
  DirectX
  Excel 

This always comes to mind: https://axelriet.medium.com/how-microsoft-vaporized-a-trilli...

I just helped setup a new O365 account and joined Win 11 machines to Entra (Cloud Active directory) for a company.

Total mess. The cloud services each had partial outages where I was met with "Data not available at this time" or various errors. At first I thought I was holding it wrong, but no, hours or even a day later things that didn't work suddenly worked. Going forward if I hit a wall I take a break, try again later and it works.

I am no MS fan but the integration of Win11 and O365/Azure seems to be headed in the right direction but the execution is a total mess. One beef is OneDrive integration is an idiotic duality as its not a "drive" and given special treatment by office apps such as only allowing auto save when saving to Onedrive.

MS, get your shit together.

I personally find a lot of Microsoft software products to be a little buggy. Use Linux desktop for a while then use Windows and you'll see what I mean.

C# is the best thing microsoft made, but was forced to be open sourced because of node.js.

Microsoft pays significantly less than most other big tech companies. I'm not sure why they go this route, or if they think having a few super highly paid engineers to manage/lead the lower paid ones is the way to go, but it may be related.

I feel the same about Big G, with my leading hypothesis being that they are leaning into hands free Ai too much. I certainly have direct evidence for that from Google in the form of a slop deck they sent me, and perceived evidence through Google Cloud degradation.

Big companies always have internal conflicts and politics. Looking at Microsoft's products, you can see similar product lines competing with each other, and they're a mess. Personally, I think C# is a well-polished language, but the frameworks are terrible.

Google is similar.

All of Microsoft's recent products feel unstable and unfinished to me. Honestly, I think all big companies become bureaucratic and end up the same way. Google, in particular, had issues with the Antigravity IDE. And Gemini is also terrible.