The outbound IP and HELO format for Office 365

Regularly, Office 365 is asked by other email receivers about the way our mail servers and IP addresses are set up, and the need to conform to a particular standard. That standard (which is more of a convention implemented by some receivers, not all of them) is that the IPs have Forward-Confirmed Reverse DNS, and these also…

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Exchange Online increases its URL filtering

One of the ways in which Exchange Online detects spam, malware, and phishing is through URL filtering. We use a variety of sources, you can find them here: https://technet.microsoft.com/en-us/library/dn458545(v=exchg.150).aspx We use URL reputation lists in the following way (including but not limited to): At time-of-scan, if a message contains a URL that is on one of…

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Phishing, magic, Stuxnet, and how they all work together

Part 1 – There’s more to me than just fighting spam If all you know of me is through this blog, then you’ll know I’ve been involved in the fight against spam, malware, and phishing for over a decade. On the other hand, those of you who know me in person or have checked out…

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Hooking up additional spam filters in front of or behind Office 365

Note: This blog post reflects my own recommendations. Over here in Exchange Online Protection (EOP), people sometimes ask me why we don’t recommend hooking up multiple layers of filtering in front of solution. That is, instead of doing one of these: Internet -> EOP -> hosted mailbox Internet -> EOP -> on-prem mail server ……

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Why we believe strange things

This post doesn’t have anything to do with cyber security. It’s one of those “It’s my blog and I can write what interests me” posts. A couple of years ago I read Robert Cialdini’s book Influence: The psychology of persuasion. It’s considered one of the classics on how to persuade other people to your point of…

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Why does my email from Facebook, that I forward from my outlook.com account, get rejected?

Why is my (your) email bouncing when I (you) forward it? Recently, many people have been asking me why their email from Facebook, that they forward from their outlook.com or Hotmail account to another account, bounces after they forward it? That is: Facebook -> outlook.com (forward) -> Hotmail/Yahoo/Gmail -> bounces back Why does this happen?…

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Seven things to know about Safety Tips

As I posted on this blog a couple of months ago, and as we posted on the Office blog last month, Office 365 is going to be releasing Safety Tips over the next few weeks. In this blog post, I go into more about how they work. 1. Outlook on the web has more Safety…

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Taking the hassle out of email authentication

Last month in Cologne, Germany, at the Certified Senders Alliance conference, I gave a presentation entitled “Taking the hassle out of email authentication.” Below is a slightly modified format of my slide show. Enjoy! Taking the hassle out of email authentication from Terry Zink

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Outlook.com DKIM signing done, now on to hotmail.com

A couple of months ago, I wrote a blog post that we were starting to roll out DKIM signing for our consumer email accounts sending from @outlook.com. These are for accounts that have been migrated from the old Hotmail/outlook.com infrastructure and onto our new Exchange Online infrastructure. Not all accounts have been migrated yet, so…

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Understanding Safety Tips in Office 365

Exchange Online Protection (EOP) already protects you with industry-leading spam and malware prevention. However, these attacks are so well crafted that they look legitimate. Sometimes putting messages into the Junk Email folder isn’t enough. EOP will automatically verify the sender and add a Safety Tip within an email message to warn you about potentially harmful…

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What Gmail’s changes in their web interface means to you as a customer of Office 365

A few weeks ago, Gmail made several changes to better reflect the security status of messages sending to its service. I am a user of Gmail and I appreciate what they are doing. If you’re a customer of Office 365, what does this mean for you? If you send email to Gmail and you don’t…

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Can TLS make the user experience better?

This blog post reflects only my opinion about encryption and the protection of sensitive personal information. It is not reflective of anyone else’s views and is only how I interpret the state of the industry. And it may be wrong. Read on at your own discretion. The other day, I was talking to a financial…

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Abstract art and the Final Ultimate Solution to the Spam Problem

I think I finally thought of something relevant to cybersecurity and my last post on why we should study art. This may be a stretch, but read on and tell me what you think. Every once in a while, a newbie to the world of fighting spam comes into one of the discussion lists or…

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Why study art?

I’ve got an unusual topic to discuss today – art history. You may be wondering “Um, why are you talking about art history on a blog about cybersecurity?” To which I reply “It’s my blog and I like writing about what I want to write about.” So, without further ado, let’s talk about art. *…

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A Powershell script to help you validate your DKIM config in Office 365

One of our support engineers (not me, so let’s give credit where credit is due) wrote a script to help you, as a customer of Office 365, validate for DKIM configuration once you have enabled it in the Admin Portal. We’ve added a few more checks to make it more clear, but you can also…

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