What the new iOS 27 Messages drawing tool does
The iOS 27 drawing tool in Messages is an integrated version of Apple’s Markup feature that lets you sketch, annotate, and send drawings directly inside a conversation on iPhone and iPad, without switching to another app or changing screen orientation. Previously, Messages hid a basic drawing panel behind landscape mode, which made casual sketching awkward and easy to miss. Now, Drawing appears as a dedicated item in the iMessage app drawer, giving the same Markup toolset you might know from Photos or Mail a permanent place in your chats. You can doodle a quick map, circle part of a photo, or add handwritten notes and send them as image messages. According to Lifehacker, Drawing is part of a broader Messages refresh in iOS 27 that also improves reliability, notifications, and search.
How to start a Messages app sketch on iPhone and iPad
To start a Messages app sketch in iOS 27, open any conversation, then tap the plus (+) button next to the text field. This opens the iMessage app drawer, where you’ll see the new Drawing option alongside other tools like Photos and Audio. Tap Drawing to launch a blank canvas that works in both portrait and landscape orientation, so you no longer need to rotate your device. From here, you can draw and send without leaving Messages. When you’re done, tap the send arrow to drop your sketch directly into the thread as an image. Your contact will see it even if they are not on iOS 27, since it arrives as a standard picture they can open or save.
Using Markup tools: pens, shapes, text, and stickers
Once the Drawing canvas opens, you get the full Markup toolkit, not a stripped-down scribble pad. You can switch between a pen, highlighter, crayons, and a paintbrush to create different line styles and textures. Color options let you add emphasis or make playful sketches. For cleaner visuals, insert shapes such as arrows, rectangles, or speech bubbles, then drag their handles to resize and position them. Markup also supports typed text boxes, so you can combine handwriting and standard text, and you can drop in signatures or stickers for added personality. When you finish your Messages sketch, the final image appears in the chat like any other photo, where it can be tapped to view in full, forwarded, or saved to Photos for later reference.
Annotating and collaborating across your Apple devices
Because Drawing is built on Apple Markup, it fits neatly into your cross-device routine. You can start a sketch in Messages on iPhone, annotate a screenshot or photo, then view that image later on iPad or Mac as part of the same conversation. iOS 27 also brings faster loading and syncing across devices, so message threads with drawings should appear more quickly on all your hardware. On the desktop side, macOS 27 Golden Gate adds the same Markup tools to Notes and Freeform, making your sketching experience more consistent when you move between devices. While Drawing itself lives in Messages on iPhone and iPad, the Markup language is shared, so anything you draw remains editable in other supported apps where Markup is available.
How Drawing fits into the broader iOS 27 Messages upgrade
The new iOS 27 drawing tool is one piece of a wider set of Messages improvements aimed at convenience and clarity. Lifehacker reports that iOS 27 adds customizable controls for the text field button, letting you swap or remove the voice message shortcut if you keep hitting it by mistake. Messages will also try resending failed messages on its own and now shows a separate send indicator for each message, so you can see when a large video is still sending while later texts have already gone through. Reaction notifications in busy group chats are consolidated into a single alert, and you can search by phone number or nickname. Together, these updates make Messages feel quicker and easier to manage while putting creative tools like Drawing within easy reach.
