On-premises data gateway - Network Request Returned Unexpected Error

Background: I'm running a PowerApps application and connecting to a 2014, 32bit sql server via an on premises datagateway on a virtual machine running windows server 2016. I had the gateway up and running for months until I needed to change my password as part of company policy. When I changed my password, the gateway failed. I logged into the Gateway and tried to change the password but I had a few failures. 

The issue I'm having is "Network request returned unexpected error". I've installed and re-installed at least 5 times, and restarted the virtual machine several times. I downloaded the latest gateway version and the latest .Net version at suggested by the gateway. Prior to downloading the latest version, I re-installed an April 2020 version and  it seemed to get me further than the current version. The April version at least prompts me to select my azure AD account but when the configurator tries to show the organizational sign in it just closes and gives me an error. 

I'm really at a loss here - it's been about a week of troubleshooting and still have not found a solution. I installed the gateway on my laptop without issue but can't get it to work on the virtual machine. Any suggestions?

The current log file from the July 2020 on premises gateway version is as follows: 

EnterpriseGatewayConfigurator.exe Information: 0 : Initialize EnterpriseGatewayMainViewModel
EnterpriseGatewayConfigurator.exe Information: 0 : GetConfiguratorStateAsync
EnterpriseGatewayConfigurator.exe Information: 0 : Value SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Client is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Value SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.1\Client is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Value SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Value SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.2\Client is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Value SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Client is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Value SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\TLS 1.0\Client is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Value SOFTWARE\Microsoft\.NETFramework\v4.0.30319 is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Value SOFTWARE\WOW6432Node\Microsoft\.NETFramework\v4.0.30319 is not defined in registry.
EnterpriseGatewayConfigurator.exe Information: 0 : Configuration client returned null
EnterpriseGatewayConfigurator.exe Information: 0 : Sign In
EnterpriseGatewayConfigurator.exe Warning: 0 : Cannot access default endpoint https://api.powerbi.com and start to use fallback endpoints. Exception: System.AggregateException: One or more errors occurred. ---> System.Net.Http.HttpRequestException: An error occurred while sending the request. ---> System.Net.WebException: Unable to connect to the remote server ---> System.Net.Sockets.SocketException: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 20.42.6.2:443
at System.Net.Sockets.Socket.InternalEndConnect(IAsyncResult asyncResult)
at System.Net.Sockets.Socket.EndConnect(IAsyncResult asyncResult)
at System.Net.ServicePoint.ConnectSocketInternal(Boolean connectFailure, Socket s4, Socket s6, Socket& socket, IPAddress& address, ConnectSocketState state, IAsyncResult asyncResult, Exception& exception)
--- End of inner exception stack trace ---
at System.Net.HttpWebRequest.EndGetRequestStream(IAsyncResult asyncResult, TransportContext& context)
at System.Net.Http.HttpClientHandler.GetRequestStreamCallback(IAsyncResult ar)
--- End of inner exception stack trace ---
at System.Runtime.ExceptionServices.ExceptionDispatchInfo.Throw()
at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
at Microsoft.PowerBI.DataMovement.GatewayCommon.ConfiguratorClientExtensions.<DiscoverEmailProperties>d__8.MoveNext()
--- End of inner exception stack trace ---
at System.Threading.Tasks.Task`1.GetResultCore(Boolean waitCompletionNotification)
at Microsoft.PowerBI.DataMovement.GatewayCommon.ServiceEnvironmentDetailsFactory.GetEnvironment(String emailAddress)
---> (Inner Exception #0) System.Net.Http.HttpRequestException: An error occurred while sending the request. ---> System.Net.WebException: Unable to connect to the remote server ---> System.Net.Sockets.SocketException: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond 20.42.6.2:443
at System.Net.Sockets.Socket.InternalEndConnect(IAsyncResult asyncResult)
at System.Net.Sockets.Socket.EndConnect(IAsyncResult asyncResult)
at System.Net.ServicePoint.ConnectSocketInternal(Boolean connectFailure, Socket s4, Socket s6, Socket& socket, IPAddress& address, ConnectSocketState state, IAsyncResult asyncResult, Exception& exception)
--- End of inner exception stack trace ---
at System.Net.HttpWebRequest.EndGetRequestStream(IAsyncResult asyncResult, TransportContext& context)
at System.Net.Http.HttpClientHandler.GetRequestStreamCallback(IAsyncResult ar)
--- End of inner exception stack trace ---
at System.Runtime.ExceptionServices.ExceptionDispatchInfo.Throw()
at System.Runtime.CompilerServices.TaskAwaiter.HandleNonSuccessAndDebuggerNotification(Task task)
at Microsoft.PowerBI.DataMovement.GatewayCommon.ConfiguratorClientExtensions.<DiscoverEmailProperties>d__8.MoveNext()<---

EnterpriseGatewayConfigurator.exe Information: 0 : (False) MSAL 4.7.0.0 MSAL.Desktop Microsoft Windows NT 6.2.9200.0 [08/14/2020 20:30:21 - 4f8b1904-9edd-4bcc-84d2-e1ba4e6acd75] (UnknownClient: 0.0.0.0) MSAL MSAL.Desktop with assembly version '4.7.0.0'. CorrelationId(4f8b1904-9edd-4bcc-84d2-e1ba4e6acd75)
EnterpriseGatewayConfigurator.exe Information: 0 : (False) MSAL 4.7.0.0 MSAL.Desktop Microsoft Windows NT 6.2.9200.0 [08/14/2020 20:30:21 - 4f8b1904-9edd-4bcc-84d2-e1ba4e6acd75] (UnknownClient: 0.0.0.0) === InteractiveParameters Data ===
LoginHint provided: False
User provided: False
UseEmbeddedWebView: NotSpecified
ExtraScopesToConsent:
Prompt: select_account
HasCustomWebUi: False

EnterpriseGatewayConfigurator.exe Information: 0 : (False) MSAL 4.7.0.0 MSAL.Desktop Microsoft Windows NT 6.2.9200.0 [08/14/2020 20:30:21 - 4f8b1904-9edd-4bcc-84d2-e1ba4e6acd75] (UnknownClient: 0.0.0.0) === InteractiveParameters Data ===
LoginHint provided: False
User provided: False
UseEmbeddedWebView: NotSpecified
ExtraScopesToConsent:
Prompt: select_account
HasCustomWebUi: False

EnterpriseGatewayConfigurator.exe Information: 0 : (False) MSAL 4.7.0.0 MSAL.Desktop Microsoft Windows NT 6.2.9200.0 [08/14/2020 20:30:21 - 4f8b1904-9edd-4bcc-84d2-e1ba4e6acd75] (UnknownClient: 0.0.0.0)
=== Request Data ===
Authority Provided? - True
Scopes - https://analysis.windows.net/powerbi/api/user_impersonation
Extra Query Params Keys (space separated) -