iOS 27 Finally Fixes Three Frustrating Bugs in Messages App

Apple’s upcoming iOS 27 update focuses heavily on overall system stability, performance optimizations, and bug fixes across core built-in applications like Safari, Mail, and Calendar. The release also fixes three major Messages app bugs, including auto-retrying failed texts (via 9to5Mac).

The first major fix targets the frustrating experience of unsent messages. Previously, tapping send on a text while moving into low-coverage areas often meant the message failed silently. If you immediately swiped home or switched applications, you might not notice the failure until hours later, requiring you to manually re-open the chat and tap the red exclamation icon to retry sending.

With iOS 27, Apple has implemented an automatic background retry system. The app will quietly monitor network connectivity and re-attempt to transmit the failed message as soon as a reliable signal returns, eliminating the need for manual intervention.

The second fix addresses media delivery bottlenecks inside active chat threads. On older iOS releases, sending a high-resolution photo or video created a systemic queue. If the media file got stuck during upload, a blue progress bar would stall at the top of the chat, effectively blocking all subsequent text messages, photos, or clips from going through until the original upload resolved or failed entirely.

iOS 27 completely decouples media sending by enabling continuous, independent delivery. Each photo, video, or text snippet now receives its own separate background progress queue. If a large video transfer slows down on a weak connection, your plain text messages and lighter media will continue to send instantly.

Finally, Apple is delivering much-needed reliability improvements to cross-device synchronization. For years, users who regularly jump between an iPhone, iPad, and Mac have complained about delayed message delivery, missing text threads, or out-of-order conversations on secondary devices.

Apple has now overhauled the underlying Cloud Sync infrastructure for Messages to ensure chat histories stay updated in real time across the entire Apple ecosystem. The final version of iOS 27 is expected to release for all supported iPhone models in early autumn.