Prompt Injection Attacks Are the New Email Threat Boston Businesses Need to Watch

Illustration of an email inbox with a security shield representing prompt injection protection in Microsoft 365

Prompt injection attacks are a new kind of email threat that targets the AI reading your inbox instead of the person reading it. In August 2026, Microsoft rolled out prompt injection protection in Defender for Office 365 specifically because attackers found ways to hide instructions inside ordinary-looking emails that trick Microsoft 365 Copilot into leaking […]

Windows 10 End of Support: How Boston Businesses Should Handle the ESU Price Hike

An older laptop running Windows on a Boston small business office desk

Windows 10 stopped receiving free security updates on October 14, 2025, and Microsoft is not walking that back. Businesses that still run it can buy Extended Security Updates (ESU) to keep getting patches, but the price doubles every year and the program caps out after three years. If your office still has Windows 10 machines, […]

August 2026 Patch Tuesday: What Boston Businesses Need to Know

IT professional applying a Windows security patch on a laptop in an office

Microsoft’s August 2026 Patch Tuesday fixed 421 vulnerabilities, and one of them was already being used in attacks before the update shipped. If your office runs Windows 10, Windows 11, or Windows Server, that single flaw is the one to check off first this week. Microsoft’s August 2026 Patch Tuesday addressed 421 CVEs, including three […]

Microsoft 365 Business Plans Get More Storage and Security in 2026

Small business office employee checking email security alerts on a laptop

Microsoft is quietly upgrading every Microsoft 365 Business plan this summer. If you run Business Basic, Standard, or Premium, your mailboxes are getting more storage and your email links are getting rescanned at the moment someone clicks, and none of it costs extra. The rollout finishes by August 1, 2026, and it lands in your […]

DMARC Email Authentication: What Boston Businesses Need to Know in 2026

Padlock icon overlaid on an email inbox screen representing DMARC email authentication

DMARC email authentication is a DNS record that stops criminals from sending fake email that appears to come from your company’s domain, and Gmail and Outlook now use it to decide whether your legitimate mail even reaches the inbox. If your domain doesn’t have one, some of your invoices, newsletters, and client replies are already […]

Business Email Compromise: The $3 Billion Fraud Boston Businesses Can’t Ignore

Business professional reviewing a suspicious email on a laptop, representing business email compromise fraud

Business email compromise, known as BEC, tricks an employee into wiring money or changing a payment based on an email that looks like it came from a boss, a vendor, or a client. The FBI’s Internet Crime Complaint Center logged $3,046,598,558 in reported BEC losses in 2025, the second-costliest cybercrime category behind investment fraud. For […]

Microsoft 365 Copilot Security Risks: What Boston Businesses Should Check First

Boston small business employees reviewing files on a laptop before enabling Microsoft 365 Copilot

Microsoft 365 Copilot security risks come mostly from old file permissions, not the AI itself. Copilot can only see what a signed-in employee already has access to, so if your SharePoint, OneDrive, and Teams sharing has been left loose for years, Copilot will surface that data in seconds when someone asks the right question. Microsoft […]

Microsoft 365 Price Increases Are Here: What Boston Businesses Should Check Now

Microsoft’s commercial pricing changes took effect on July 1, 2026, and most Microsoft 365 business plans went up. If your renewal hasn’t hit yet, now is the time to look at what you’re actually paying for and whether you’re on the right plan before the new pricing locks in. Here’s what changed, who it affects, […]

July 2026 Patch Tuesday: What Boston Businesses Need to Patch This Week

IT professional applying a security patch to a laptop in an office

Microsoft’s July 2026 Patch Tuesday fixed roughly 569 vulnerabilities, the largest single release in the program’s history, and two of them were already being used in real attacks before the fixes shipped. If your business runs an on-premises SharePoint Server or Active Directory Federation Services (AD FS), the short version is: patch this week. Everyone […]

SharePoint Server Vulnerability: What Boston Businesses on Old Systems Should Do Now

IT technician checking an on-premises server rack in an office server room

A SharePoint Server vulnerability is being actively exploited right now, and CISA has told federal agencies to patch it immediately. If your Boston business still runs an on-premises SharePoint Server (not SharePoint Online, which is unaffected), you need to check your patch status this week, not next quarter. CISA added SharePoint Server flaw CVE-2026-45659 to […]