Cloud Service - Extending Support - Reboot loosing SSL website bindings

Hi @Jon Elster
It sounds like you’re installing your SSL cert and binding at runtime on the VM, but every time Azure reprovisions (reimages) that VM on reboot it drops anything you’ve manually put into C:\ or the LocalResource. By design Cloud Service role OS disks are ephemeral, so your cert and IIS binding vanish on a reboot.

Use the built-in certificate support in Cloud Services:

• Upload your PFX into an Azure Key Vault in the same subscription/region as your Cloud Service.
• In your Cloud Service resource (portal/PowerShell/ARM), on the Certificates blade, add a reference to that Key Vault secret.
• In ServiceDefinition.csdef (classic) or your ARM template (extended support), declare:

<Certificate name="MyCert" storeLocation="LocalMachine" storeName="My" />
<InputEndpoint name="HttpsIn" protocol="https" port="443" certificate="MyCert" />

• In ServiceConfiguration.cscfg, add

<Certificates>
  <Certificate name="MyCert" thumbprint="YOUR_THUMBPRINT" thumbprintAlgorithm="sha1" />
</Certificates>

Persist any custom files (configs, scripts) that your role needs across reboots:

• Don’t rely on C: or LocalResource – those get wiped on reprovision.
• Store files in Azure Blob storage or an Azure File share and download them in a startup task.
• Or attach an Azure Data Disk to your role (configured in ServiceDefinition.csdef) – that disk stays intact across reboots for that instance.

Automate additional binding or setup via a startup task:

• If you have custom PowerShell or batch steps (e.g. extra IIS config), add them under <Startup> in your ServiceDefinition so they run on every VM boot.
  Let me know if you have any further assistances needed.