iOS 27 Is Quietly Fixing the Most Annoying Parts of the Messages App
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This year’s OS 27 releases aren’t only about AI. In fact, the original rumors last fall suggested that iOS 27’s watchwords would be performance and stability, and while the new Siri’s arrival has overshadowed nearly everything else, Apple hasn’t forgotten about the simpler improvements.
After all, Siri showed up at this year’s release more because of delayed timing than anything else. In an alternate universe where Apple managed to deliver “Siri 2.0” in iOS 18.4 as it originally planned, iOS 27 would be in a very different place by now. Even so, we’d still have been due for Apple to take one of its usual steps back from packing in a ton of new features and focus on stability and smaller improvements.
Set aside Siri AI, and that’s what we’re seeing in most of Apple’s other apps. Even those features that tie in AI are largely quality-of-life improvements, such as natural language support in the Calendar app and better suggestions and improved search in Mail.
The same holds true for Apple’s Messages app. In addition to expanded integration of Writing Tools — now known as Write with Siri — Apple has introduced a ‘Drawing’ app, expanded RCS support, and fixed a few annoying little bugs that have crept up over the years. Here’s what’s new so far.
The Drawing Board
In a development that many believe points to the upcoming foldable iPhone, Messages now includes a built-in sketchpad. This goes beyond the handwriting mode that appeared when holding your iPhone sideways into a full-fledged creative doodling tool.
This will be especially fun on an iPad with an Apple Pencil, where it should feel instantly familiar to anyone who has drawn in apps like Notes or Preview — or even just used it to mark up an image or a PDF file — but it’s also fully usable on an iPhone with just your fingers.
Drawing is called up from the plus sign like any other tool in Messages, and opens into a blank canvas with all the usual markup tools at the bottom. From here, you can choose pen styles and colors or use the plus sign to insert stickers, text, shapes, and even your signature or a loupe to magnify part of the image.
One-Tap Contextual Suggestions
We touched on this last week in our roundup of how iOS 27 will make some of Apple’s built-in apps smarter, but it’s actually working now in iOS 27 beta 2.
Contextual suggestions now appear below any messages where Apple Intelligence determines you might want to take some further action, such as adding a reminder or calendar event or making a note.
This is similar in concept to the highlighted “data detectors” that have long been part of iOS where you can tap on a specific time or date to create a calendar event, or tap on a phone number to place a call. However, the difference in iOS 27 is that these are now using AI to analyze those messages and fill in a lot of the detail for you.
For example, if someone mentions getting together on the weekend, an “Add to Calendar” button will open an event creation screen that includes key details like where and when. Or, if someone asks you to share some photos you took at a party, a “Search for Photos” button will automatically track down photos related to what the other person is asking for.
RCS Reactions and Threads
The second iOS 27 beta delivered a nice surprise for iPhone-Android communications in the form of proper Tapback-style reactions and threaded replies, similar to how iPhone users have been communicating via iMessage for years.
These two features were officially added in the RCS Universal Profile 2.7 specification in June 2024 — the same month that Apple began rolling out RCS support in the iOS 18 developer betas. Although many hoped these features would make it into the final iOS 18 release, Apple’s software engineers had their hands full with Apple Intelligence and other features, which undoubtedly led to these landing on the back burner.
When they also missed the iOS 26 release, many wondered if they were ever coming, especially after Apple added end-to-end encryption (E2EE) — an RCS 3.0 feature — in iOS 18.5. Thankfully, that didn’t mean Apple had skipped RCS 2.7; it just believed E2EE was a higher priority.
The new RCS features in iOS 27 work just like they do in iMessage chats. As long as the Android user you’re communicating with has a reasonably recent version of Google Messages, they’ll see threaded replies and proper reactions instead of the more basic “liked your message” and “replied to your message” texts. RCS being the carrier-dependent animal that it is, this may not be functional everywhere yet — and iOS 27 is still in developer beta, too — but in my testing it’s working as designed between my iPhone 17 Pro Max and Google Pixel 6.
Get the Audio Button Out of the Way
Although we’ll never know for sure if Tim Cook was actually scared of being hunted down by Justin Bieber, Apple has resolved a complaint publicly made by the singer last year by allowing users to evict the audio button from the text entry field in Messages.
Until now, it’s only been possible to switch the default function of the button between recording audio or starting dictation. However, that binary option has been replaced by a new “Show in Text Field” option in Settings > Apps > Messages that offers a third choice: None.
As the name suggests, this will make the audio button go away entirely, resulting in a clean, unadulterated text field — and zero risk of accidentally interrupting your music or seeing Apple employees in one of Bieber’s “rear naked choke holds.”
Fixing Even Greater Annoyances
Even though we’ve probably all fat-fingered the audio button once or twice in our iPhone-owning lives, it’s not a show-stopping problem for most folks. However, Messages has plenty of other peculiarities that are. The good news? Apple appears to be addressing a good number of these.
- You’ll no longer need to worry about finding messages that failed to send lingering in the background. Now, if you fire off a message and then swipe away to another app and that message doesn’t make it out for whatever reason, iOS 27 will try again until it can. It’s one of those things that makes us wonder what took Apple so long; since tapping “Send” commits the message to being sent, your iPhone should be doing its best to make sure that actually happens.
- You can keep the conversation going while waiting for a photo or video to send. Another big win for anyone who has ever suffered on a slow connection: sending a photo or a video won’t interrupt the rest of your conversation. Instead, iOS 27 will keep sending that in the background while letting you continue your chat even as you wait for the blue progress bar to crawl across the screen. When the photo does go through, it should also show up in the proper spot in the conversation.
- Apple says multi-device conversation syncing is improved. We’ll have to wait and see how this one plays out in the real world. I’ve already noticed it seems to be better in the developer betas, but it’s only been two weeks, and I can’t rule out a placebo effect. Note that you’ll likely need to be running OS 27 on all of your devices to take advantage of this, so don’t be surprised if things are a bit out of sync on your Mac if you haven’t yet updated to macOS 27 Golden Gate — they certainly were for me.
Apple also promises faster loading of messages, thumbnails instead of big grey boxes for offloaded media, and improved search for offloaded media and conversations.
