Certificate refresh for the Windows Admin Center (WAC)

This article has not been completed yet. However, it may already contain helpful Information and therefore it has been published at this stage.

Prerequisites:

• Some linux based environment

Links that might be useful in this case:

• Setting up WSL2 (Windows Subsytem for Linux) on Windows 10

Anyone who has been using the Windows Admin Center for longer than 60 days will probably run into a certificate problem. The latest browser from Microsft, called Edge, will then no longer allow access to the WAC portal at all.

1) Scenario 1 - Local WAC Installation

The easiest way to get a new certificate is to initiate a repair installation. Enclosed are the necessary steps, if you have a local WAC - installation.

You could also use a separately created certificate at this point by providing its Thumprint ID to perform the necessary reassignment.

2) Scenario 2 - WAC - Gateway Installation

In order to avoid getting an expired certificate again in 60 days, I create myself a certificate which is valid for 10 years.

For this I switch to my Linux environment. In my case a WSL installation based on Ubuntu.

# Creating a cert - folder
mkdir certs

# Changing Directory
cd certs

# Generating the Cert

openssl req -x509 -newkey rsa:4096 -sha256 -days 3650 -nodes \
  -keyout cert.key -out cert.crt -extensions san -config \
  <(echo "[req]"; 
    echo distinguished_name=req; 
    echo "[san]"; 
    echo subjectAltName=DNS:<fqdn>
    ) \
  -subj "/CN=<fqdn>"
  
# Looking for the new generated certs
ls

# Certificate conversion - CRT+Key = PFX
openssl pkcs12 -export -in cert.crt -inkey cert.key -out wac.pfx

# Obtaining the certificates via Windows Explorer
\\wsl$\Ubuntu\home\bruendlt\certs

The changeover process:

# var
$GatewayServerName="<Hostname WAC - Gateway>"

# session
$Session=New-PSSession -ComputerName $GatewayServerName

# copy
Copy-Item -Path "$env:USERPROFILE\Downloads\wac.pfx" -Destination "$env:USERPROFILE\Downloads\wac.pfx" -ToSession $Session

# cert import
Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {Import-PfxCertificate -FilePath "$env:USERPROFILE\Downloads\wac.pfx" -CertStoreLocation Cert:LocalMachine\My -Exportable -Password (ConvertTo-SecureString -String '<PFX - File Password>' -AsPlainText -Force)}

# extract appId
$pattern = '(?<=\{).+?(?=\})'
$appId=[regex]::Matches((Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {netsh http show sslcert})[8], $pattern).Value

# thumprint
$Thumbprint = (Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {Get-ChildItem  -Path Cert:\LocalMachine\MY | Where-Object {$_.Subject -Match "$GatewayServerName"} | Select-Object FriendlyName, Thumbprint, Subject, NotBefore, NotAfter| Sort-Object -Property NotAfter -Descending  | Select-Object -first 1}).Thumbprint

# delete old binding
Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {netsh http delete sslcert ipport=0.0.0.0:443}

# add new binding
$NetshArgumentList = "http add sslcert ipport=0.0.0.0:443 certhash="+$Thumbprint+" appid=`'{"+$appId+"}`'"
Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {Invoke-Expression "netsh $using:NetshArgumentList"}

# restart
Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {Restart-Service ServerManagementGateway}

#add certificate to trusted root certs
$Subject = (Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {Get-ChildItem  -Path Cert:\LocalMachine\MY | Where-Object {$_.Subject -Match "$GatewayServerName"} | Select-Object FriendlyName, Thumbprint, Subject, NotBefore, NotAfter| Sort-Object -Property NotAfter -Descending  | Select-Object -first 1}).Subject
start-sleep 10
$cert = Invoke-Command -ComputerName $GatewayServerName -ScriptBlock {Get-ChildItem Cert:\LocalMachine\My\ |where subject -eq "$using:Subject"}
$cert | Export-Certificate -FilePath $env:TEMP\WACCert.cer
Import-Certificate -FilePath $env:TEMP\WACCert.cer -CertStoreLocation Cert:\LocalMachine\Root\

References:

https://it-infrastructure.solutions/windows-admin-center-hybrid-hub-to-the-cloud-azure-part-2/

Setting up WSL2 (Windows Subsytem for Linux) on Windows 10

Generating self-signed certificate files (Linux - Debian)