Describes how to secure your OWIN/ASP.NET 5 endpoints in ServiceFabric without having to log on to each VM and do stuff.

ApplicationManifest.xml

<ApplicationManifest>
  ...
  <ServiceManifestImport>
      <ServiceManifestRef ServiceManifestName="SERVICENAME" ServiceManifestVersion="1.0.0" />
      <Policies>
        <EndpointBindingPolicy CertificateRef="MyCertificateName" EndpointRef="ServiceEndpoint" />
      </Policies>
  </ServiceManifestImport>
  ...
  <Certificates>
    <EndpointCertificate Name="MyCertificateName" X509FindValue="CERT_THUMBPRINT"/>
  </Certificates>
</ApplicationManifest>

installCertOnVm.ps1

# Upload certificate to VMs.

Param
(
    [Parameter(Mandatory = $true)]
    [string]
    $SourceVault,
    
    [Parameter(Mandatory = $true)]
    [string]
    $ResourceGroup,
    
    [Parameter(Mandatory = $true)]
    [string]
    $CertificateUrl,

    [Parameter(Mandatory = $true)]
    [string]
    $VMPrefix,

    [Parameter(Mandatory = $true)]
    [int]
    $VMCount
)

$CertStore = "My"

for($i = 0; $i -lt $VMCount; $i++) {
    $VMName = "$VMPrefix$i"
    Write-Information "Getting VM info for VM $VMName"

    $VM = Get-AzureRmVM -ResourceGroupName $ResourceGroup -Name $VMName
    $VM = Add-AzureRmVMSecret -VM $VM -SourceVaultId $SourceVault -CertificateStore $CertStore -CertificateUrl $CertificateUrl

    Write-Information "Updating VM $VMName"
    
    try
    {
        Update-AzureRmVM -ResourceGroupName $ResourceGroup -VM $VM
    }
    Catch
    {
        $ExceptionMessage = $_.Exception.Message
        Write-Warning $ExceptionMessage
    }
}

ServiceManifest.xml

<ServiceManifest>
  ...
  <Resources>
    <Endpoints>
      <Endpoint Name="ServiceEndpoint" Type="Input" Protocol="https" Port="443" CertificateRef="MyCertificateName" />
    </Endpoints>
  </Resources>
</ServiceManifest>

uploadCertToKeyVault.ps1

# Before execution make sure to have logged in to Azure (Login-AzureRmAccount)
# and selected the correct subscription (Select-AzureRmSubscription)

Param
(
    [Parameter(Mandatory = $true)]
    [string]
    $CertificateName,

    [Parameter(Mandatory = $true)]
    [string]
    $PfxFile,

    [Parameter(Mandatory = $true)]
    [string]
    $VaultName
)

$resourceId = $null
try
{
    $existingKeyVault = Get-AzureRmKeyVault -VaultName $VaultName
    $resourceId = $existingKeyVault.ResourceId

    Write-Host "Using existing valut $VaultName in $($existingKeyVault.Location)"
}
catch
{
    throw "Unable to find KeyVault named $VaultName"
}

$securePass = Read-Host 'Password: ' -AsSecureString
$password = [Runtime.InteropServices.Marshal]::PtrToStringAuto([Runtime.InteropServices.Marshal]::SecureStringToBSTR($securePass))

$PfxPath = Resolve-Path $PfxFile

$cert = New-Object System.Security.Cryptography.X509Certificates.X509Certificate2 $PfxPath, $password
$bytes = [System.IO.File]::ReadAllBytes($PfxPath)
$base64 = [System.Convert]::ToBase64String($bytes)
$jsonBlob = @{
   data = $base64
   dataType = 'pfx'
   password = $password
   } | ConvertTo-Json

$contentbytes = [System.Text.Encoding]::UTF8.GetBytes($jsonBlob)
$content = [System.Convert]::ToBase64String($contentbytes)
$secretValue = ConvertTo-SecureString -String $content -AsPlainText -Force

Write-Host "Writing secret to $CertificateName in vault $VaultName"
$secret = Set-AzureKeyVaultSecret -VaultName $VaultName -Name $CertificateName -SecretValue $secretValue

$output = @{};
$output.SourceVault = $resourceId;
$output.CertificateURL = $secret.Id;
$output.CertificateThumbprint = $cert.Thumbprint;

return $output;

@MegaMax93 Turns out the script needs modifications because service fabric VMs are in a scale set now.
I added it to my Azure RM template where it deploys the cluster key. I am using the same key vault so it only needed a new entry in vaultCertificates inside the osProfile of the virtual machine scale set.

Here's an alternative to installCertOnVm.ps1 that works with VM Scale Sets. It assumes that you're adding a certificate to the first key vault referenced by the VMSS; change the commented line to suit your needs:

# Upload certificate to Virtual Machine Scale Set.

Param
(
    [Parameter(Mandatory = $true)]
    [string]
    $SourceVault,

    [Parameter(Mandatory = $true)]
    [string]
    $ResourceGroup,

    [Parameter(Mandatory = $true)]
    [string]
    $CertificateUrl,

    [Parameter(Mandatory = $true)]
    [string]
    $VmssName
)

$CertStore = "My"

Write-Information "Getting Key Vault info for vault $SourceVault"
$Vault = Get-AzureRmKeyVault -VaultName $SourceVault

Write-Information "Getting VMSS info for VMSS $VmssName"
$Vmss = Get-AzureRmVmss -ResourceGroupName $ResourceGroup -VMScaleSetName $VmssName

Write-Information "Updating VMSS $VmssName"

try
{
    $CertConfig = New-AzureRmVmssVaultCertificateConfig -CertificateUrl $CertificateUrl -CertificateStore $CertStore
    $Vmss.VirtualMachineProfile.OsProfile.Secrets[0].VaultCertificates.Add($CertConfig) # NOTE: Change this as needed
    Update-AzureRmVmss -ResourceGroupName $ResourceGroup -Name $VmssName -VirtualMachineScaleSet $Vmss
}
Catch
{
    $ExceptionMessage = $_.Exception.Message
    Write-Warning $ExceptionMessage
}

Can it also work on the local cluster?
I have the certificate installed in Current User -> Personal.
Should it be able to find it there? Do I need to change something in the code, because it doesn't work locally for me.

UPDATE
This helped https://matt.kotsenas.com/posts/https-in-service-fabric-web-api