I have an Exchange 2013 server running on Server 2012 R2 that I am trying to migrate to Exchange Online with a hybrid configuration. I have setup the AD Connect without an issue. However, before I installed the HCW, I tried to run the Test-HybridConnectivity powershell in the HybridManagement module. It fails with the following errors. I believe it is an issue with TLS 1.2 so I have tried using the command "[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12" from this article but have the same error. I tested on a standard 2012 R2 server and it also fails at first but that command makes it succeed. I also tried setting the registry keys in SCHANNEL\Protocols\TLS 1.2\Server and Client and restarting. There are several clients that I will be migrating this way and all of them fail the test script.
[PS] C:\Windows\system32>Import-Module C:\Scripts\HybridManagement.psm1 [PS] C:\Windows\system32>Test-HybridConnectivity -testO365Endpoints Testing connection to mscrl.microsoft.com on port 80 Testing connection to crl.microsoft.com on port 80 Testing connection to ocsp.msocsp.com on port 80 Testing connection to www.microsoft.com on port 80 Testing connection to login.windows.net on port 443 WARNING: Ping to login.windows.net failed -- Status: TimedOut Testing connection to login.microsoftonline.com on port 443 WARNING: Ping to login.microsoftonline.com failed -- Status: TimedOut Testing connection to outlook.office.com on port 443 Performing GET on https://outlook.office.com:443 Testing connection to outlook.office365.com on port 443 Performing GET on https://outlook.office365.com:443 Testing connection to nexus.microsoftonline-p.com on port 443 WARNING: Ping to nexus.microsoftonline-p.com failed -- Status: TimedOut Performing GET on https://nexus.microsoftonline-p.com:443 Invoke-WebRequest : The underlying connection was closed: An unexpected error occurred on a send. At C:\Scripts\HybridManagement.psm1:196 char:19 + $result = Invoke-WebRequest -Method Get -Uri $uri + ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ + CategoryInfo : InvalidOperation: (System.Net.HttpWebRequest:HttpWebRequest) [Invoke-WebRequest], WebExc eption + FullyQualifiedErrorId : WebCmdletWebResponseException,Microsoft.PowerShell.Commands.InvokeWebRequestCommand