Fixing Outlook Certificate Errors

How to solve problems with Exchange Autodiscover. Certificate Error issues in particular.

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Office 365 Migration – When Do I Need to Use Third Party Tools?

This post may be late in coming, given that most smaller companies have already moved away from on-prem solutions to cloud based services for things like email and file sharing, but I feel like it’s important to stress some of the realities involved in migrating from on-prem to cloud systems. Particularly when migrating to Office 365.…

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Hardening Microsoft Solutions from Attacks

Take a minute to go over this post from Dirk-jan Mollema. Go ahead and read it. I’ll wait…

Did you realize how scary that kind of attack is? As an IT guy who specializes in Exchange server and loves studying security, that article scared the snot out of me. Based on my experience with organizations of all sizes I can say with a good bit of authority that almost every Exchange organization out there is probably vulnerable to this attack.…

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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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Designing Infrastructure High Availability

IT people, for some reason, seem to have an affinity towards designing solutions that use “cool” features, even when those features aren’t really necessary. This tendency sometimes leads to good solutions, but a lot of times it ends up creating solutions that fall short of requirements or leave IT infrastructure with significant short-comings in any number of areas.…

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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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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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