iOS 27 fixes three of the most annoying Messages bugs

Chance Miller | Jun 15 2026 - 6:03 pm PT

iOS 27 focuses heavily on bug fixes and performance improvements across apps like Safari, Mail, Calendar, and more.

In the Messages app, iOS 27 fixes what I think are three of the most frustrating bugs …

iOS 27: Three key bug fixes in Messages

First, Apple says that failed messages will automatically retry sending in iOS 27. There have been countless times when I hit send on a message, immediately swipe up and go back to my iPhone’s Home Screen, then realize later that the message I thought I sent actually failed.

In iOS 26 and earlier, this required going back to the Messages app and manually tapping the “retry” button next to the message in question. In iOS 27, however, that will now happen automatically in the background.

Second, Apple says iOS 27 enables continuous sending of photos, videos, and texts in Messages. This fixes a frustration that’s likely familiar to most iPhone users: you send a photo, it gets stuck, and a blue progress bar lingers at the top of the conversation. Until that photo finally goes through, any additional messages you send are effectively held up as well.

Top comment by IndomitableSlake

Liked by 4 people

Hopefully the third means that it will stop automatically turning off SMS forwarding from iPhone to other devices, which has been a problem for over ten years.

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In iOS 27, that bottleneck is gone. Each message gets its own progress bar and is sent independently, so a stuck photo won’t prevent subsequent texts, photos, or videos from being delivered.

Finally, iOS 27 improves Messages syncing across devices. Apple says conversations will sync more reliably between your devices, making it less likely that you’ll switch from your iPhone to your Mac and find messages missing, delayed, or out of sync.

For a full look at everything new in the Messages app with iOS 27, check out our full guide here. What do you think of the changes Apple has made to Messages in iOS 27? Let us know down in the comments.