I could access the pages just fine in other browsers, e.g. in Firefox or Microsoft Edge, but Chrome would always return a not found error message.
The fix back then was to delete cookies set by Microsoft's site as they somehow interfered with the connection.
Over the past couple of weeks, I started to get a slightly different issue when accessing Microsoft pages in the Chrome browser.
Any page on Microsoft's website, https://www.microsoft.com/, e.g. https://www.microsoft.com/en-us/software-download/windowsinsiderpreviewiso, returned a "not found error".
We are sorry, the page you requested cannot be found.
The URL may be misspelled or the page you're looking for is no longer available.
The issue was limited to a particular instance of Google Chrome. Chrome Canary, also installed on the device, Firefox, Microsoft Edge, and any other browser I tried, loaded the page and others just fine.
I knew that the issue that I experienced was not system-wide; only Google Chrome could not connect to pages on the Microsoft website while all other browsers could.
While there are plenty of possible explanations for the issue, I decided to try the tested "delete all cookies" solution that fixed the issue in 2016 first.
The page that would not load previously loaded just fine afterward.
I tested several pages on Microsoft's website and they all loaded without any issues.
I don't know how widespread the issue is; if you run into it, try clearing cookies in the browser that you experience the connection issues with to see if it resolves it.
It is possible that the issue will come back in this form or another at a later point in time. You could auto-clean cookies set by Microsoft's domain to avoid the issue but that would mean that you would have to sign in each time you want to access pages or services that require authentication.
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