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.
If you’re still using Outlook, always check if removing your email account and setting it up again is enough to get your client to start stronger authentication processes. If your account is already in iMAP format, no emails will be lost. If that doesn’t work, you should consider upgrading to a newer version of Outlook, a different email client, or a different Office platform altogether.
If you do the latter, watch out for cheap versions of Office that don’t match what you see on Microsoft’s website. Chances are it’s a scam. Even on reputable websites, I’ve seen Office being offered for just $39.99. The buyer ends up with a product key that doesn’t work and an offer to buy Microsoft 365. And you might not need the Office suite at all. Unless you’re deeply entrenched in macro-enabled Word and Excel documents, alternative suites should work just fine. Libre Office could meet your document and spreadsheet needs, and there are plenty of third-party options for email. (While Outlook remains a major player in the business world, it is losing its grip on the consumer space.
Beyond Outlook, you have options
If you like Firefox, you can try Thunderbird. It also has an email setup wizard to help you easily create your email account. Another option is EM, which is similar to Outlook. Both run on Windows and Macs. So if you’re switching between the two, any email migration should be pretty easy. The best thing is that you can usually try these types of alternative platforms for free before you buy them.
If your email is still in a downloaded PST file, you can usually find tools to migrate from one platform to another. I used Systools to easily migrate from Zoho to Microsoft 365 and Recoverytools to export an Outlook pst file to a Thunderbird format. I recommend looking for a paid tool to ensure you get support for any issues you may have.
The bottom line here is that you shouldn’t lock yourself into an outdated version of Outlook when it comes to emailing. If you haven’t received updates in years, you put yourself at risk for attacks and threats. For small businesses in particular, business email compromise is a major risk that is exacerbated by legacy platforms.
If you’re having email issues, make sure your credentials are up to date, check for ISP changes, and make sure Outlook (if that’s your preferred client) has been updated. And if you don’t like Outlook, switch to an alternative that works for you.
This is the best way to make it difficult for the bad guys to get into your systems.
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