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Tom’s Hardware
Tom’s Hardware
Technology
Bruno Ferreira

Outlook may have allowed unencrypted connections for decades, report claims — Fedora and Dovecot upgrade reveal protocol downgrade issue present since at least 2007

Ripped envelope.

An IT blogger claims to have uncovered a high-impact security vulnerability in Microsoft Outlook, which was reportedly found to have been silently downgrading secure SSL/TLS connections to unencrypted plaintext without telling anyone. This appears to affect at least Outlook 2007 through 2016, and possibly even later versions, though that's as of yet unconfirmed if this behavior is present from Outlook 2019 onwards.

The report came by way of a blog post at Marius World, where the writer describes how they came across the issue after upgrading their mail servers from Fedora 42 to Fedora Server 43 (released in October 2025). Marius started getting complaints from customers unable to receive emails. All got the same error message from the mail server: "Cleartext authentication disallowed on non-secure (SSL/TLS) connections". This meant the user's mail client was trying to use an unencrypted connection, something that's been deprecated by systems administrators for decades.

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