If You Have a Cisco Firewall, Disable this Feature NOW!!!

I don’t often have an opportunity to post a rant in an IT blog (And even less opportunity to create a click-bait headline), but here goes nothing! Cisco’s method of doing ESMTP packet inspection is INCREDIBLY STUPID and you should disable it immediately. Why do I say that? Because when Cisco ASAs/whatever they call them these days are configured to perform packet inspection on ESMTP traffic, the preferred option of doing so is to block the STARTTLS verb entirely.*

In other words, Cisco firewalls are designed to completely disable email encryption in order to inspect email traffic.…

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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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Removing Addresses from an Exchange Server with Powershell

This is probably a rare issue, but something I’ve come across in my work. Occasionally an Exchange Administrator may need to remove an Email address domain (The part of the email address that comes after the @ sign). For instance, you may be in a situation where a portion of the users in an Exchange environment are migrated to a Cloud based email solution.…

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Office 365 Hybrid Configuration Failures

This is just a quick post that is meant to help people out who are having some issues with creating a Hybrid Configuration with Office 365 and Exchange 2010 SP3. There are some serious bumps in the road that you can come across when setting this up that may cause you to spend countless hours troubleshooting without any real success.…

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Configuring Autodiscover for Internal DNS

The Issue

Ever since Outlook 2016 was released, Autodiscover has been a necessity, rather than an option.

Autodiscover allows any Mail Client that connects to Exchange server to configure the appropriate settings for communication so you don’t have to input everything manually. It’s very handy, but can cause certificate errors if not configured correctly. One issue you may run into occurs most often with Exchange Organizations with non public DNS domains like domain.local.…

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