Yeah, that's one of the things I don't like about 2.2....just the overall way it's options are setup...I can get things done and adjusted easier and faster with 1.90.

And yes I have Winstep as well....works great!

I checked my Object Desktop backup folder and I have 2 different versions of 2.20. When I hover over the .exe files 1 says file version: 9.1.1.0 and the other says file version: 9.5.1.0. Is there a difference?

I just tried 1.90 Windows won't let me install is either.

Just a guess, but what if you save the activate.exe from 2.20 and change it out for the 1.90 version and see if that would activate OD. Or am I just out of my mind.

Quoting WebGizmos,

reply 32

Again...  

Quoting WebGizmos,

reply 28

Can we please stop beating around the bush. It says "activate.exe failed to reach your server" then goes on "do I wish to activate via email?" YES....PLEASE...ACTIVATE! Can we do this or not? I really hate the newer version and would love to get my 1.90 version activated! Thanks!

I tested an old product (Fences Pro - same guts as your old OD) activation here and it worked fine.  I also checked our activation logs for those products and, while rare-ish (their frequency in the log), they are activating.

The stoppage has to be local (your PC).  I would just try shutting down any and all firewalls, AV products, including Windows defender.

While it might be more than you want to do, you can use Fiddler to perhaps see where its failing:

https://www.telerik.com/fiddler

Long since retired I am afraid.

Ok...here's a copy of what this Fiddler app created....maybe since you suggested it's use you can make heads or tails out of this.

https://www.fiddler2.com/UpdateCheck.aspx?isBeta=False
http://outlook.live.com:443
https://forums.wincustomize.com:443
http://www.msn.com:443
http://ocsp.thawte.com/MEQwQjBAMD4wPDAJBgUrDgMCGgUABBSDXMN22sHhCJ%2BQ8WDKToovi3RuCgQUxe2TXys4R35Y01fH%2F0XFREHhX78CAyHSvQ%3D%3D
https://forums.wincustomize.com:443
http://www.msn.com:443
http://static-global-s-msn-com.akamaized.net:443
http://static-global-s-msn-com.akamaized.net:443
http://static-global-s-msn-com.akamaized.net:443
http://otf.msn.com:443
http://sdcentral.stardock.com/activate/connect.html
http://googleads.g.doubleclick.net:443
https://forums.wincustomize.com:443
https://forums.wincustomize.com:443
http://www.googletagmanager.com:443
https://forums.wincustomize.com:443
https://forums.wincustomize.com:443
http://pagead2.googlesyndication.com:443
https://forums.wincustomize.com:443
http://platform.twitter.com:443
http://connect.facebook.net:443
http://adservice.google.com:443
http://adservice.google.com:443
http://www.google-analytics.com:443
http://googleads.g.doubleclick.net:443
http://syndication.twitter.com:443
http://www.facebook.com:443
http://ocsp.usertrust.com/MFEwTzBNMEswSTAJBgUrDgMCGgUABBR8sWZUnKvbRO5iJhat9GV793rVlAQUrb2YejS0Jvf6xCZU7wO94CTLVBoCEEIa8pQJhBkfUgpLxiQmp0s%3D
http://ocsp.usertrust.com/MFEwTzBNMEswSTAJBgUrDgMCGgUABBRtl6lMY2%2BiPob4twryIF%2BFfgUdvwQUK8NGq7oOyWUqRtF5R8Ri4uHa%2FLgCEBBwnU%2F1VAjXMGAB2OqRdbs%3D
http://ocsp.comodoca.com/MFEwTzBNMEswSTAJBgUrDgMCGgUABBSOJaE2H4hHYQzP74hlLuO41NG%2BEAQUHsWxLH2H2gJofCW8DAeEP7bP3vECEEwtow0eIQRZ1MX1e7uRlk4%3D
http://sdc.api.stardock.net/2011-11-17/service.asmx
http://ctldl.windowsupdate.com/msdownload/update/v3/static/trustedr/en/disallowedcertstl.cab?19c774b9c5023a41
http://crl.thawte.com/ThawtePremiumServerCA.crl
http://account.api.stardock.net:443
http://install.api.stardock.net:443
http://sdcentral.stardock.com/activate/connect.html

Because, no doubt when you activated 2.2 on 8/21/2018 4:45:56 AM, the activation file was still in:

\ProgramData\Stardock\ObjectDock

Ok...tried again and still wouldn't activate...got this instead...

"Application start: 2018-8-29 17.30.4

Downloading test internet data...

Download: success

Test internet data - failed

Please check the serial number that you have entered and ensure that it is associated with the email you used. Try to activate the product again. If you are using Stardock Central you can right-click on the product and attempt to activate without reinstalling. Please include this log file when contacting support@stardock.com."

And got his in Fiddler....

"http://sdcentral.stardock.com/activate/connect.html"

Same thing...won't activate.   This really sucks.  

Like I said..."same thing" aka "same error"...it doesn't activate...I get the same errors I've been getting...nothing new.

Easy, Web.......... I am doing what I can to get a decade old legacy app working for you.  Finding dev time, and justifying it, is not as easy as you may believe.