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Is Going Automated. Three Things to Check.

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Sidestreet Signal  ·  Issue 04  ·  September 2026

Automation is moving into the workflow.
Keep the judgment where it belongs.

Software is moving from suggesting what to do to actually doing things on behalf of customers and teams. Here are three changes worth watching, and what I'd do about them.

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Short, practical, low-volume. Marketing, web, production and communications from the people who do the work.

    Built with Kit

    The interesting shift right now isn't another new AI tool. It's how quickly software is moving from suggesting what to do to actually doing things on behalf of customers and teams.

    A browser that completes a purchase for someone. An identity system that quietly retires the login method half your staff uses. A pricing engine that changes the number a customer sees based on what it knows about them. Each of those is useful. Each of them also needs a person somewhere who can say what the system is allowed to decide on its own. Here are three changes worth watching, and what I'd do about them.

    01  ·  What changed

    Three shifts
    worth your attention.

    01  ·  Web & digital

    The browser is starting to do the clicking

    Google recently expanded Gemini in Chrome on Android, including an "auto browse" feature for Google AI Pro and AI Ultra subscribers in the U.S. that can handle multi-step tasks like updating recurring orders, booking parking and organizing travel.

    That sounds like a consumer feature. It's also a website change. We've spent years designing sites around a person reading, deciding and clicking. Increasingly, some of those interactions will happen through software acting for that person. That puts more value on things that were already good practice: clear page structure, plain language, predictable forms, accurate product and service information, and fewer strange steps between intent and completion.

    The takeaway: Don't redesign your website for robots. Just make sure a customer, human or otherwise, can clearly understand what you offer and how to take the next step.

    Read the Google announcement

    02  ·  Technology & security

    SMS is becoming the backup plan, not the security plan

    Microsoft began making passkeys the default authentication experience in Entra ID on September 1, 2026, for users enabled for SMS or voice. Those users are being nudged toward passkeys, and Microsoft plans to retire its own SMS and voice delivery for Entra authentication on February 1, 2027. Organizations that still need those methods will need a customer-managed telecom provider.

    There's a larger point here than Microsoft. The familiar "password plus a text message" setup has lasted a long time because it's easy. It's also increasingly a target for phishing and social engineering. Passkeys, Windows Hello for Business and FIDO2 hardware security keys are much harder to steal that way.

    The takeaway: If your company still treats text-message MFA as the finish line, it's worth moving the line.

    Read Microsoft's guidance

    03  ·  Marketing & customer trust

    "Personalized" pricing is getting a harder look

    The FTC is asking for public comment on a proposed enforcement policy around personalized pricing, specifically businesses using personal information to calculate what an individual customer might be willing to pay. This isn't a new blanket ban on dynamic pricing. But the FTC is making its concern pretty clear: if customer data is being used to change the price someone sees, failing to disclose what's happening may run into existing consumer-protection law.

    There's an important line here for marketing teams. Personalization can be useful. Different messaging, better recommendations and more relevant experiences can make things easier for a customer. Quietly changing the economics of the deal based on what you know about that individual is a different decision.

    The takeaway: The more your systems personalize automatically, the more important it becomes to know exactly what they're changing, and whether you're comfortable explaining it to the customer.

    Read the FTC announcement

    A useful rule across every channel
    Automate the work.
    Keep the rules visible.
    Know where a human still owns the decision.
    02  ·  Put it to work

    Three things
    I'd check this month

    01
    Walk one customer path without filling in the blanks.

    Pick your most important action: request a quote, make a purchase, schedule something, contact sales. Start from your homepage and try to complete it using only what the site actually tells you. If you have to already know where to go, the path isn't clear enough.

    02
    Find out who is still using SMS for MFA.

    Not who can use something stronger. Who actually is. For Microsoft environments, start moving those users toward passkeys, Windows Hello for Business or another phishing-resistant method before it becomes a rushed migration later.

    03
    Write down what your automation is allowed to decide.

    AI, ad platforms, CRMs and personalization tools can increasingly make choices without someone manually approving every one. Pick the important systems and ask a simple question: what is this allowed to change on its own? If nobody knows the answer, that's the part to fix.

    A useful place to start if you're not sure what needs fixing

    Marketing Audit
    + Roadmap

    We offer a Marketing Audit + Roadmap for teams that know something could be working better but don't need somebody immediately selling them a giant new marketing plan. We look at the current setup, meaning your website, messaging, marketing activity, measurement and customer path, then turn what we find into a prioritized roadmap.

    What's working stays. What isn't gets called out. And if something doesn't need to be rebuilt, we'll say that too.

    It's a fixed-scope starting point, not a requirement to sign up for an ongoing retainer.

    03  ·  Where we can help

    Senior help,
    without the layers.

    If either of these priorities is sitting on your list, our senior team can help shape the plan and stay on the work through launch.

    Web & digital
    A website that reads clearly to people and to the software acting for them.

    Structure, plain language, predictable forms and accurate service information, built and maintained as one working system.

    Explore web & digital
    Managed technology
    Identity, MFA and the boring security work that stops the expensive problems.

    Managed IT and technology services for growing organizations that need someone accountable for the stack.

    Explore managed technology
    04  ·  Let's talk

    Need a second set
    of senior eyes?

    Send us the thing you're trying to improve: a campaign, website, growth question, technology problem or half-formed idea. We'll tell you plainly whether we can help.

    Start a conversation

    workwithus@hellosidestreet.com  ·  864-574-3811

    Issue 04 Questions Answered

    Can't find the answer you're looking for? Get in touch

    What is Gemini "auto browse" in Chrome, and does it affect my website?

    +
    -

    Auto browse is a Gemini feature in Chrome on Android, available to Google AI Pro and AI Ultra subscribers in the U.S., that can carry out multi-step tasks for a person, such as updating a recurring order, booking parking or organizing travel. It affects your website because some visitors will now arrive as software acting on someone's behalf. Sites with clear structure, plain language, predictable forms and accurate service details will work for those visitors. Sites that rely on the visitor already knowing where to click will not.

    When is Microsoft retiring SMS and voice authentication for Entra ID?

    +
    -

    Microsoft made passkeys the default authentication experience in Entra ID on September 1, 2026, for users enabled for SMS or voice, and plans to retire its own SMS and voice delivery for Entra authentication on February 1, 2027. Organizations that still need SMS or voice after that will need a customer-managed telecom provider. The safer path is to move users to passkeys, Windows Hello for Business or FIDO2 security keys before the deadline.

    Why are passkeys more secure than text-message MFA?

    +
    -

    A text message code can be phished, intercepted or socially engineered out of a person. Passkeys, Windows Hello for Business and FIDO2 hardware keys are bound to the device and the site, so there is no code for an attacker to trick someone into handing over. That's why Microsoft and others are treating SMS as a fallback rather than the primary factor.

    Is personalized pricing illegal?

    +
    -

    Not as a blanket rule, and this isn't legal advice. What changed is that the FTC is seeking public comment on a proposed enforcement policy around personalized pricing, meaning the use of personal information to calculate what an individual customer might pay. The FTC's stated concern is that changing a customer's price based on their data without disclosing it may run into existing consumer-protection law. If your systems adjust pricing automatically, know what they're changing and whether you'd be comfortable explaining it.

    What is the Sidestreet Marketing Audit + Roadmap?

    +
    -

    It's a fixed-scope engagement for teams that know something could be working better but don't need a giant new marketing plan sold to them first. We review your current website, messaging, marketing activity, measurement and customer path, then turn what we find into a prioritized roadmap. It's a starting point, not a requirement to sign up for an ongoing retainer.

    What is Sidestreet Signal?

    +
    -

    Sidestreet Signal is a short, practical newsletter from Sidestreet Media in Spartanburg, SC. Each issue picks a few real changes across marketing, web, production, technology and communications, explains what they mean for a growing business, and pairs them with specific moves you can make that week. It's written by founder Josh Kuhn, sent by email through Kit, and archived here on hellosidestreet.com.

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