Important Windows deadline and impactful Outlook and Gmail changes

Plus – CEO’s sound off on AI Savviness and Verizon Price Hikes

Author

David Radin
May 19, 2025

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“A person who knows how may always have a job. But a person knows why will always be his boss.”

— John Maxwell

In this issue:

  1. Windows deadline is this fall; don’t miss it

  2. Microsoft and Google ‘enhance’ their email

  3. Time Management in the Age of A.I.

  4. Latest news & articles that impact you

    1. Major corp bans emails in meetings

    2. Google Gemini’s hug upgrade

    3. Verizon price hikes

    4. CEO’s believe execs lack what it takes for AI

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Windows deadline is this fall; don’t miss it

If you have Windows 10, you can get a free update to Windows 11 – as long as you meet the technical requirements and your Windows 10 (which you can find out via PC Health Check). Since Windows 10 reaches its official end of life in October, meaning no more support, this could be particularly important – especially when you consider that the world is moving to AI as a foundation of life and Windows 11 supports AI better.

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Time Management in the Age of A.I.

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Microsoft and Google ‘enhance’ their email

I love this news that Google is changing the way gmail (and presumably mail in Google Workspace) deals with junk – because they are finally catching up with a technique that we pioneered 2 decades ago. It’s shielded emails.

Back then, we created a company and product called SpamSlicer which gave users a protected in box by allowing you to off-the-cuff create a new email address for specific senders, such as your bank or vendors, and then if somebody started spamming that address, would let you block the entire email address and bug out to a new one with just a couple clicks and keystrokes. The concept also allowed you to better recognize scams who were pretending to be vendors with whom you do business.

Google later started giving you the ability to emulate part of that – where you can vary your email address by placing a plus sign and some text right before the @ to identify the sender. Such as [email protected]. But it was an incomplete solution.

Now the rumor mill is expecting Google to let you make shielded emails – in essence the same concept that we ran in the 90s. We should look forward to this as a great enhancement to our Gmail and Google workspace emails, because it’s one of the best ways to keep spam out reliably with 0% chance of them incorrectly identifying a good email as junk. But that will depend on what the final implementation looks like.

Too bad they didn’t do it decades earlier. And from my perspective, too bad we didn’t patent it. ;-)

 New Compliance Requirements in Outlook and Gmail

Both Google and Microsoft have added touches that make it harder for non-compliant emails to reach you. Generally speaking, that means email sent from senders who don’t comply with more stringent requirements when they send. The goal is to make it more difficult, for instance, for a sender to make believe they are somebody else with the goal of tricking you to reply, click or release sensitive information.

Again, this type of requirement has been a long time coming – in good part because email is an open system. Microsoft’s policy went into effect on May 5; Google’s on April 1st.

The flip side of this new more stringent environment is that if you are a legitimate sender, but don’t conform to the tighter requirements, your email will have a harder time reaching your intended recipient.

Latest News and impactful releases:

The last word

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David