A Treatise on Information Security

One famous misquote of American Founding Father Ben Franklin goes like this, “Anyone who would sacrifice freedom for security deserves neither.” At first glance, this statement speaks to the heart of people who have spent hours waiting in line at the airport, waiting for a TSA agent to finish groping a 90 year old lady in a wheel chair so they can take off their shoes and be guided into a glass tube to be bombarded with the emissions of a full body scanner.…

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Anatomy of a Certificate Error

The most important step in diagnosing a specific security error involves determining what the error is telling you. There are a few things that can cause certificate errors, and what you do depends entirely on what is causing the error to begin with. Once you know what the error is telling you, it becomes much easier to figure out what you need to do next.…

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How Does Autodiscover Work?

Autodiscover is one of the more annoying features of Exchange since Microsoft reworked the way their Email solution worked in Exchange 2007. All versions since have implemented it and Microsoft may eventually require its use in versions following Exchange 2016. So how does Autodiscover work?

Some Background

Prior to Exchange 2007, Outlook clients had to be configured manually.…

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Configure Exchange Autodiscover

As of the release of Outlook 2016, Microsoft has chosen to begin requiring the use of Autodiscover for setting up Outlook clients to communicate with the server. This means that, moving forward, you will need to configure Exchange Autodiscover to get Outlook working properly.

This page contains some information and some links to other posts I’ve written on the subject of Autodiscover.…

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Theory: Understanding Digital Certificates

One of the more annoying tasks in administering a publicly available website that uses HTTPS (Outlook Web App, for example) is certificate generation and installation. Anyone who has ordered a certificate from a major Certificate Authority (CA) like Godaddy or Network Solutions has dealt with the process. It goes something like this:

  1. Generate a Certificate Signing Request (CSR) on the web server
  2. Upload the CSR to a CA in a Certificate Request
  3. Wait for the CA to respond to your Request with a set of files
  4. Download the “Response” files
  5. Import the files on the Web Server

Once that gets done, you will (usually) have a valid certificate that allows the server to use SSL or TLS to encrypt communications with client machines.…

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