Email woes gotcha worried? How to fix problems and fend off attacks

Email is one of those tools that people keep saying will one day die and be replaced by a better communication platform. And yet, because it’s near-universal and works so well across platforms, it’s still there.

However, working across platforms is not the same as working well for everyone at all times. I’ve seen a lot of concern about the rising number of email-based attacks, and a lot of complaints from people who have email problems in general – with many blaming Outlook or some other client for the recent problems.

In fact, the underlying cause might be simpler: ISPs have switched to more modern authentication processes (to thwart attacks) and some email clients can’t handle the changes. Case in point: Microsoft slowly but surely disabling basic authentication and moving to a better level of protection. (If your email platform still uses basic authentication, attackers are almost certainly trying to crack your passwords using password spraying and credential harvesting.)

Here’s what you can do to solve basic email problems and still make sure you’re protected from attackers.

Email Troubleshooter 101

In general, if you’re having trouble accessing email using the same app you always have (and the same password), the first thing you should do is verify your password. An easy way to do this is to log into the web version of your email platform. When you come in, you have the correct credentials. I’ve seen instances where an ISP has changed their password complexity requirements, and it’s only through logging in online that I learn of that fact. (This would also be a good time to add two-factor authentication to your personal email accounts, especially those used to authenticate financial institutions.)

You may also find that you are actually using older versions of Outlook that do not support modern authentication. While Microsoft 365 may have dropped support for versions earlier than 2013 Service Pack 1, other email servers may have continued to support these older platforms. Your ISP may have changed email requirements — and you missed the memo.

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