How does forcing current versions of Office (365) and Windows (11 or 10 Pro) affect my ability to continue using my remote desktop into my older still-functioning versions of ...?

Question

Here's the problem. I have older computers which continue to function that I use OFFLINE, with remoting capabilities from my NEWER versions of Microsoft 365 and Windows 10 Pro through my internet-disconnected network. The older computers have versions of Microsoft Office going ALL THE WAY BACK TO MICROSOFT OFFICE VERSION 1.0, my first purchase of Office several decades ago. The older computers also have versions of Microsoft Windows going ALL THE WAY BACK TO Windows 3.11, each computer including going forward through Windows 98, XP, & Vista Ultimate. I was concerned that END-OF-LIFE UPDATES or other updates would foul-up those computers, so I took them OFFLINE and DISABLED AUTO-UPDATING and SEVERED their connections to the World Wide Web.

Each of them STILL FUNCTION, even the versions that everyone said would "BLOW-UP" if we all did not upgrade to your newer Y2K versions.

The pre-Y2K computers did NOT blow-up AND THEY STILL WORK AND I KEEP THEM OFFLINE TO ALLOW THEM TO CONTINUE TO WORK. I will NOT be forced by anyone, including Microsoft, to STOP using them. (I especially like the DukeNukem1.0)

The only one I no longer have is my Windows Server 2000/2003, which came with Visual Studio Enterprise Edition, and the ONLY REASON that one no longer works is a BIRD LANDED ON THE TRANSFORMER OUTSIDE WHERE I LIVE, although the good news is the damn bird no longer lives, deservedly for wiping out my WinSrv2k3 laptop. He FRIED a horrible death and fell to the ground, the bird not the laptop.

I have working concepts and work on those older computers that I have used for OVER 30 YEARS and still use (Family history, personally developed databases & programs, my personally recorded songs and musical score and recordings, etc...).

NO ONE ELSE IS ALLOWED TO CONNECT TO THOSE COMPUTERS. And when I remote into those computers, I go OFFLINE from the World Wide Web Internet.

In short, I have sort of a History of Microsoft versions that still work. (I even have Commodore computers 64&128 that still work too!)

If I am forced to update to the NEW version TLS on my Internet-allowed computers, WILL THAT DISABLE MY ABILITY TO REMOTE INTO MY OLDER VERSION COMPUTERS

or

WILL I STILL be able to remote into them?

***Move from Microsoft 365 and Office / Subscription, account, billing / For home / Windows***

Answer 1

I don't worry about a secure or encrypted connection on my computers that are on my private-never-connected-to-the-outside-world network. So, I'm not sure this helps me. It's beginning to sound like I need to just disconnect from the world entirely and end all my subscriptions.

When security becomes OVER-security and denies me my functionality, it becomes a worthless product.

I'll have to find some other way, maybe just direct connection in my private-never-connected-to-the-outside-world network and continue using the old computers offline but be ethernet-connected to my private-never-connected-to-the-outside-world network.

The only other option for me is to write some code that puts my network firewall blocking and connection to older TLS in play while I am on my non-internet system.

Why do I continue believing in Microsoft when they constantly foul up older system functionality with constant change.

Answer 2

Thank you for sharing your situation. I understand how important it is for you to keep your older computers and software working. These systems are clearly valuable to you, both for the work you do and for their personal significance.

If you decide to write custom code, you could develop a simple script or application to handle the specific needs of your network, including managing firewall rules and connections to older TLS versions.

Best regards,

Karlie

Answer 3

Hello,

If you update your RDP clients to use a newer version of TLS (such as TLS 1.2 or 1.3) on your Internet-allowed computers, it may affect your ability to remote into older version computers that only support an older version of TLS (such as TLS 1.0 or 1.1). This is because the RDP client and server must agree on a common security protocol for the connection to be established.

You can concentrate on two Group Policy configurations for securing remote connections:

Computer Configuration > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > Security

• Require use of specific security layer for remote (RDP) connections: This setting allows you to specify the security layer that must be used for RDP connections. If TLS is not supported, you may consider using RDP security layer.
• Set client connection encryption level: This setting lets you define the encryption level for RDP client connections.

These settings will help you ensure that your Remote Desktop connections are secure and encrypted to the appropriate level.

I hope this information helps.

Best regards,

Karlie