Encrypted emails in Microsoft’s older email client—called “classic Outlook” as opposed to “new Outlook”—have once again encountered problems. The company confirms on this support page that users of ...

Microsoft has confirmed a known issue that prevents recipients from opening encrypted emails in classic Outlook.

Microsoft is looking into a newly identified issue in classic Outlook that prevents users from opening certain encrypted ...

There is no fix available, but you can always revert to an older version.

A new Outlook (Classic) update is preventing Windows users from opening encrypted emails. Microsoft confirms the bug and ...

A new Microsoft-issued software patch for Outlook (Classic) on Windows 11 inadvertently broke encrypted email support - ...

A widespread issue has emerged in classic Microsoft® Outlook following the Windows 11 patch update KB5074109 on 13 Jan, 2026. POP account users have reported that Outlook is unable to exit cleanly.

Q. Recently, I’ve become concerned about the privacy of sending email. What’s a cheap and easy way to protect my email messages? A. I’ve consistently preached that the use of unencrypted email is the ...