Issue Using Collector as Proxy for Agent Installation

Good Day Community,

I have encountered an Issue installing Agent on a Windows Server
The Windows Server I want to Install the Agent on does not have access to the internet, therefore I want to use the Collector to serve as a Proxy.
The Collector is a Linux Server.
The Windows Server can communicate with the Collector.
I am using the option of Pairing using the Locally provided configuration files, which are the files and packages I downloaded and extracted from the Insight Platform.
Whenever I use the Windows command that was provided in the Insight Agent Proxy Configuration Documentation. It brings this error Back

“We can’t connect you to *” Check your internet connection and firewall restrictions, then restart the installation"

I have added the HTTPSPROXY with details of my collector’s IP and port, but it still brings up the same error.
I have also manually created the proxy.config file in the same installation path with the details of my Collector IP, But still brings up the same error

Whenever I Double-click on the Installer itself without using the command.
It brings this error Back.

“You are connected to the Platform, but platform data is blocked by a firewall, Ensure all * traffic is whitelisted.
We Can’t find the certificate needed to make your platform connection secure. Ensure all config files are at “My Installation Path””
All files downloaded and extracted are at " My Installation Path".

Kindly Assist with the solution of this Problem.
What are the ports and protocols I need to open on both the Windows Server side, Firewall Side, and Collector side?
I would be available to give more information if required.

Attached to this Topic are screenshots of the error messages.
Rapid7 Agent Installation Error

I have experience with this, however, I configured this for Linux servers without internet access proxying data to a Linux collector. Let’s regroup on Monday and I can offer some insight into how I was able to get this configured. I followed the below articles.

Proxy Configuration | Insight Agent Documentation
Certificate Package Installation Method | Insight Agent Documentation