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The underlying issue may be that you are both on the same subnets. &nbsp;What is the netmask for your 1.1.1.207 and for the 1.1.1.1 server?<br />
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Also, are those the actual IP address or did you change them for this posting? &nbsp;The 1.x.x.x addresses are public and shouldn't be used privately.
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I am not using 1.x.x.x I changed the the first three octets. &nbsp; 1.1.1. &nbsp;was just easy to type. &nbsp; &nbsp; &nbsp; <br />
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I should have labeled the diagram better. &nbsp;The laptop labeled 1.1.1.207 works but it is assigned an IP address on the local subnet and &nbsp;I have been requested to separate these out. &nbsp; The Laptop on the bottom labeled 192.168.100.50 is the one I am having issues with. &nbsp; &nbsp;<br />
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When I connect to the second Firewallusing the the VPN I get an IP address of 192.168.100.x and I can ping/ssh/remote desktop/connect over Http and Https to all other servers. &nbsp; The only one I am having an issue with is 1.1.1.1 &nbsp; I have gone through the configs on the firewall, switches and the router and there is no special routing for 1.1.1.1 anywhere I can find. &nbsp; &nbsp;The 1.0.1.60 switch is connected to 10.0.1.90 over a fiber connection and is on the same subnet.
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I argued with support for the server and they finally admitted there was routing on the server itself and posted the routing table for me to view. &nbsp; &nbsp; They had a static route for 192.0.0.0/8 to an invalid address which was causing the issue.
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<div class="content wysiwyg-content">
<a href="https://filedb.experts-exchange.com/incoming/2019/12_w51/1439318/Drawing1.jpg" target="_blank" title="Network Diagram (22 KB)"><img alt="Network Diagram" class="file-block lazyload" style="max-width: 394px;" data-src="https://filedb.experts-exchange.com/incoming/2019/12_w51/1439318/Drawing1.jpg" /></a>Possible Routing issue.<br />
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I am trying to connect to a specific server over a vpn connection. &nbsp; &nbsp;<br />
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I have configured the Firewall to provide an IP address in the 192.168.100.0 range. &nbsp; When I connect to it I can see the local network. &nbsp;I can ping and connect to the local servers. &nbsp;The single server I can not connect to is 1.1.1.1. &nbsp;I can ping and connect to other servers on the 1.1.1.0/24 subnet without issue.<br />
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I ran a tracert from my local computer and I get to 1.0.1.90 then 1.1.1.1. &nbsp; If I run it from the remote computer over the vpn I get to 1.0.1.90 then nothing. &nbsp; <br />
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I have checked the firewall and there are no rules specific to 1.1.1.1 &nbsp;on it or on 1.0.1.90 which is the default Gateway. &nbsp;There is a route for the 192.168.100.0/24 on the Gateway<br />
&quot;Route 192.168.100.1 255.255.255.0 1.0.1.61&quot;<br />
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I have talked to the vendor who provided the server and they say there is nothing on the server which would block any traffic. &nbsp;<br />
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Any suggestions on what to check next?
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Drawing1.jpg

Possible Routing issue.

I am trying to connect to a specific server over a vpn connection.    

I have configured the Firewall to provide an IP address in the 192.168.100.0 range.   When I connect to it I can see the local network.  I can ping and connect to the local servers.  The single server I can not connect to is 1.1.1.1.  I can ping and connect to other servers on the 1.1.1.0/24 subnet without issue.

I ran a tracert from my local computer and I get to 1.0.1.90 then 1.1.1.1.   If I run it from the remote computer over the vpn I get to 1.0.1.90 then nothing.   

I have checked the firewall and there are no rules specific to 1.1.1.1  on it or on 1.0.1.90 which is the default Gateway.  There is a route for the 192.168.100.0/24 on the Gateway
"Route 192.168.100.1 255.255.255.0 1.0.1.61"

I have talked to the vendor who provided the server and they say there is nothing on the server which would block any traffic.  

Any suggestions on what to check next?

Issue routing to single IP Address

Networking is the process of connecting computing devices, peripherals and terminals together through a system that uses wiring, cabling or radio waves that enable their users to communicate, share information and interact over distances. Often associated are issues regarding operating systems, hardware and equipment, cloud and virtual networking, protocols, architecture, storage and management.

Networking

A virtual private network (VPN) is a network that uses a public telecommunication infrastructure, such as the Internet, to provide remote offices or travelling users access to a central organizational network securely. VPNs encapsulate data transfers using secure cryptographic methods and other security mechanisms to ensure that only authorized users can access the network and that the data cannot be intercepted.

A router is a networking device that forwards data packets between computer networks. Routers perform the "traffic directing" functions on the Internet. The most familiar type of routers are home and small office cable or DSL routers that simply pass data, such as web pages, email, IM, and videos between computers and the Internet. More sophisticated routers, such as enterprise routers, connect large business or ISP networks up to the powerful core routers that forward data at high speed along the optical fiber lines of the Internet backbone. Though routers are typically dedicated hardware devices, use of software-based routers has grown increasingly common.