Enabling Message Encryption in Office 365

As I mentioned in an earlier post, email encryption is a sticky thing. In a perfect world, everyone would have Opportunistic TLS enabled and all mail traffic would be automatically encrypted with STARTTLS encryption, which is a fantastic method of ensuring security of messages “in transit”. But some messages need to be encrypted “at rest” due to security policies or regulations.…

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QuickPost: What do Exchange Virtual Directories Do?

This is just a quick little reference post to answer a question that isn’t well covered. Most Exchange admins are familiar with how to set the Virtual Directories in Exchange after a new server is added or a after initial deployment. What’s less clear to most is what those VDirs actually do as far as Exchange’s capabilities are concerned.…

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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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Do I need Anonymous Relay?

Problems

If you have managed an Exchange server in the past, you’ve probably been required to set things up to allow printers, applications, and other devices the ability to send email through the Exchange server. Most often, the solution to this request is to configure an Anonymous Open Relay connector. The first article I ever wrote on this blog was on that very subject: http://wp.me/pUCB5-b . …

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How Does Exchange 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 what is Autodiscover and how does it work?

Some Background

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

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Configuring 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, Autodiscover will need to be properly configured.

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

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Exchange Autodiscover – The Active Directory SCP

In a previous post I explained how you can use a SRV record to resolve certificate issues with Autodiscover when your Internal domain isn’t the same as your Email domain. This time, I’m going to explain how to fix things by making changes to Exchange and Active Directory that will allow things to function normally without having to use a SRV record or any DNS records at all, for that matter.…

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Exchange Transaction Logs – Reducing the Confusion

Exchange Transaction Logs are, in my opinion, one of the most horribly documented parts of Exchange server. There’s a lot of misinformation out there as well as a lot of misunderstanding. If you look for an answer to questions that most people have about them, you’ll run across poorly written documentation that barely explains what they are, let alone how they work.…

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Public Folder Migration Issues Resolution for KB 977921 With PFDAVAdmin

The Issue

When you migrate from Exchange 2003 to Exchange 2007+ you can run into a number of problems that are due entirely to the differences in how Exchange handled public folders. One of these problems, as explained in KB 977921, is particularly annoying. The problem shows up after the public folders are replicated to an Exchange 2007/2010 server (Exchange 2013 uses a completely new system for Public Folders, and migration to it is completely different so the issue doesn’t really appear for that version of exchange).…

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Removing Addresses from an Exchange 2007/2010/2013 Server

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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