question

Hi @ssujeshsasidharan-7673 ,

I'm not sure how Octopus Deploy send deployment requests to IIS. It is not a deployment tool from Microsoft. So I want to discuss with you the situation when use WebDeploy or manual deploy.

Does IIS process one request at a time though it receives multiple requests. what happens when IIS Receives multiple requests to update Applicationhost.config file ?

Updating the applicationhost.config file is actually a process that opens it, writes to it and closes it. While the Windows system handles multiple processes to read and write the same file, only one process is allowed to read and write and lock the file state. No other process can read or write until the current process completely closes the file and releases the lock.

How can we monitor these requests which are being processed by IIS and if it fails or hangs how can we determine it. if we already have a tool which can do this then please let us know.

It is not IIS but the Windows system that handles the update deployment request. The Windows system copies and pastes the application files to the server's disk, and sets the physical path of the new site in the applicationhost.config file to point to this folder. So I think you should monitor modifications to the applicationhost.config file.
Set a basic audit policy on applicationhost.config file is a great way to monitor deployment.

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Best regards,
Bruce Zhang