Chicago IT Support & Cyber Security | Forward Technologies

Chicago-based Forward Technologies delivers IT support and cyber security to businesses in the Chicago area and nationwide.

Microsoft Finally Makes Sending From Email Aliases a Real Exchange Online Feature

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A cartoon IT administrator opening an old Microsoft 365 tenant closet packed with dusty SMTP aliases, abandoned domains, migration leftovers, and forgotten addresses, highlighting why administrators should audit existing aliases before enabling Send From Alias organization-wide.This is one of those Microsoft 365 features that makes you wonder why it took this long.

Microsoft has finally moved Send From Alias in Exchange Online to general availability. The feature lets you send an email using any SMTP alias assigned to your mailbox, and the recipient actually sees that alias as the sender.

Seems pretty obvious, right?

For years, Exchange aliases were basically a one-way street. You could have sales@company.com, info@company.com, and yourname@company.com all assigned to the same mailbox and receive mail at every one of them.

But sending from one of those aliases was another story. [Read more…]

We Finally Got Everyone Using MFA. Now It’s Changing

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A clean cartoon showing the evolution of Microsoft authentication from password, to password plus SMS code, to a passkey using Windows Hello with fingerprint, face, or PIN authentication.For years, the security advice was simple: turn on multifactor authentication.

IT people repeated it endlessly. Microsoft pushed it. Insurance companies started requiring it. Cybersecurity audits looked for it. Eventually, most businesses got the message.

Users learned the routine. Enter the password. Wait for the text message. Type in the 6-digit code. Get back to work.

Now Microsoft is changing all of that. [Read more…]

Windows 10 Gets Another Reprieve, And This Was Easy to See Coming

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A humorous cartoon comparing Windows XP and Windows 10 as two stubborn old operating systems refusing to retire while Microsoft looks frustrated.Back in the fall, I said Microsoft was going to have to extend Windows 10 support again. The numbers made it obvious. There were simply too many machines still running it, and not enough realistic paths to Windows 11 for a huge chunk of users. Now here we are.

Microsoft has quietly added another year to its Extended Security Updates program for Windows 10, pushing support out to October 12, 2027. That gives users an extra twelve months of critical security patches beyond the original cutoff, and it confirms what a lot of us in IT already suspected. Windows 10 was never going away on Microsoft’s original timeline. [Read more…]

The AI Free Ride Is Starting to End

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Cartoon-style illustration of a worried office worker sitting at a desk in front of a laptop while reviewing a report that shows rapidly rising costs. The report features a gauge in the red zone and a stack of coins, suggesting escalating expenses. Large windows behind him reveal a city skyline at sunset, while coffee cups and a laptop on the desk reinforce the corporate office setting. The image symbolizes growing concern over the rising cost of AI tools and enterprise technology spending.The AI subsidy era is ending, and the bills are finally showing up.

Microsoft is reportedly cutting back internal Claude Code licenses and steering developers toward GitHub Copilot CLI instead. It matters because this is Microsoft, not some cash-strapped startup. This is the company that poured billions into OpenAI, owns GitHub, and runs one of the biggest cloud businesses on earth. If even Microsoft is looking at token-based usage and deciding the math does not work, everyone else should probably pay attention. [Read more…]

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