[m365weekly] #199

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Issue #199

☁️Productivity & Modern Workplace

New Outlook for Windows Support for Export to PST. The New Outlook for Windows now supports exporting mailbox items to PST files, addressing a long-standing request. However, the process is significantly slower compared to the classic Outlook due to structural differences.

My Honest Advice To Someone That Wants Clarity With M365. Chaos in Microsoft 365 often happens due to overly complex setups that isolate teams and workflows. Simplify your environment with one team for your organization, minimal channels, clear naming conventions, flat folder structures, and defined app usage. This approach aligns tools with real-world collaboration, reduces confusion, and helps everyone focus on work instead of searching for it.

How to find everything you copied in Windows 11 with the WIN + V clipboard. Windows 11’s clipboard history, accessed with WIN + V, lets you view and manage everything you’ve copied. Enable it under Settings > System > Clipboard. Use the shortcut to paste, pin, or delete items. It’s a handy tool for multitasking, though history clears on shutdown unless items are pinned. Simple yet effective for productivity.

[FEATURED STORY] Phishing from within: The exploit Microsoft ignored for years

Source: Direct Send Exploit: Risk to Your Organization

The big picture. Microsoft’s Exchange Server feature Direct Send, originally meant to let devices like printers send emails internally without authentication, is now being exploited by attackers to send phishing emails inside organizations without needing credentials. This abuse bypasses standard security checks because emails appear to come from within the tenant, allowing phishing payloads with PDF attachments or QR codes that evade typical detection methods. Despite the risk being longstanding, Microsoft only recently added a setting to allow admins to disable Direct Send by default, acknowledging the security gap it creates. The lack of authentication and default enablement of this feature until now effectively let attackers “send mail as internal users” without compromise.

Why is it important? This exploitation highlights a major security oversight by Microsoft, as Direct Send was left enabled and unprotected for years, enabling attackers to infiltrate organizations without breaching accounts or credentials. Because it requires no login and uses predictable smart host addresses, it’s trivial for attackers to abuse once they know an organization’s domain and user emails. Organizations must now act quickly by disabling Direct Send if unused, enforcing strict DMARC policies, hardfail SPF checks, and setting static IPs in SPF records to prevent spoofing and phishing abuse. Educating users about phishing via QR codes and suspicious attachments is also critical. Without such steps, internal phishing campaigns that evade usual email security controls will continue to put enterprises at risk.

☁️Copilot & AI

Real-time voice conversation with M365 Copilot. Starting August 2025, you’ll be able to use real-time voice interactions with Microsoft 365 Copilot Chat and Copilot across platforms. Simply tap the voice chat icon to start speaking, and you can interrupt or redirect the conversation as needed. This feature will be enabled by default for users with a Copilot license on iOS, Android, web, Windows, and Mac.

M365 Copilot Chat vs. Copilot Research Agent: Use Cases and Examples. Microsoft 365 Copilot Chat is your go-to for quick, real-time assistance with tasks like drafting content or summarizing emails within apps. The Copilot Research Agent, however, excels at tackling complex, multi-step queries, delivering detailed reports with citations by scouring enterprise and external data. Use Chat for speed and simplicity, and Research Agent for depth and thoroughness.

Microsoft Copilot Agents: What You Can Build Without Writing Code (And When You’ll Need To). Microsoft’s ecosystem offers four key types of AI agents: out-of-the-box, no-code, low-code, and full-code. Out-of-the-box agents like Copilot in Teams or Office apps are great for personal or business use, depending on your login. No-code agents, via tools like SharePoint or Agent Builder, let you add knowledge sources easily. Low-code agents leverage Copilot Studio for more complex tasks, while full-code agents in Azure allow for custom models and fine-tuning. Each has its strengths … more in the video.

☁️Sysadmin Stuff

Filter Spam Using Mail Flow Rules in Exchange Online. Mail flow rules in Exchange Online help you combat spam by detecting suspicious keywords or patterns in emails and assigning a Spam Confidence Level (SCL). These rules can move flagged emails to junk, quarantine, or prepend alerts to the subject line. Combined with anti-spam policies, they create a robust defense against phishing, malware, and other email threats.

Create Migration Endpoint in Microsoft 365. Migration endpoints in Microsoft 365 define remote server connections for mailbox migrations. You can set them up manually through the Exchange Admin Center or PowerShell by providing server details and credentials. These endpoints store migration settings and enable data transfer to Exchange Online. Verifying the configuration ensures they are ready for use in migration tasks.

PowerShell Email Domain Migration Guide. If you’re migrating email domains in Microsoft 365 and Active Directory, this guide walks you through updating UPNs, cleaning up Exchange Online mailboxes, and adding proxy addresses in AD. It emphasizes proper permissions, testing in non-production environments, and monitoring changes to ensure accuracy. Each step includes detailed PowerShell scripts and considerations for safe execution and rollback.

☁️Security & Data Governance

Understand the Difference Between SMS Sign-In and SMS MFA. SMS sign-in and SMS-based MFA serve different purposes in Microsoft 365. SMS sign-in is passwordless, ideal for frontline workers, while SMS MFA adds a second layer after a password. Both have vulnerabilities, especially to phishing and SIM swap attacks. To enhance security, consider app or hardware-based MFA and monitor user activity. Admins can identify SMS sign-in users via Microsoft Entra or PowerShell.

Who Is Still Using Text Messaging For Multi-Factor Authentication? You can enhance your tenant’s security by identifying users still relying on SMS for multi-factor authentication (MFA) and transitioning them to more secure methods. Use Azure Log Analytics to analyze sign-in logs, create a group for SMS users, and restrict SMS to this group. Gradually migrate users to safer MFA options while monitoring progress over time.

Enhancing Microsoft 365 security by eliminating high-privilege access. Microsoft is eliminating high-privileged access (HPA) across Microsoft 365 applications to enforce least privilege access and strengthen security. By re-engineering systems, enforcing secure authentication protocols, and implementing strict monitoring, the company reduces risks tied to compromised services or token exposure.

☁️Noteworthy (long)reads

Tech to worry about. With rising tensions, Iran’s cyber capabilities targeting critical infrastructure demand immediate attention. Ensure all PLCs and IoT devices are secured, focusing on removing default, weak, or blank passwords. Start with internet-facing devices but assess internal networks too. Older equipment may pose additional challenges. For MSPs, addressing these vulnerabilities showcases your expertise and could strengthen client trust.

Convincing SMBs to Invest in M365 Business Premium: Strategies and Steps. Microsoft 365 Business Premium offers SMBs advanced security features like phishing protection, device management, and conditional access, surpassing Business Standard. It helps safeguard against modern threats, minimizes downtime, and ensures compliance. By addressing common SMB misconceptions, demonstrating ROI, and providing ongoing support, you can highlight its value as an essential investment for business continuity and protection.

DATES TO KEEP IN MIND

October 14, 2025 – Windows 10 (Home, Pro, Enterprise, Education, IoT Enterprise) end of support – source

October 14, 2025 – Office 2016, Office 2019, Exchange Server 2016, Exchange Server 2019 end of support – source

October 2026 – Retirement of Microsoft Publisher app which has been a part of Office Suite for years.

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