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Why Won’t My Mac Messages App Send Images After Dragging and Dropping in macOS 26.2?
macOS Tahoe 26.2 introduced a persistent bug affecting the Messages application that prevents users from sending images through the standard drag-and-drop method. When attempting this action, users encounter a “Not Delivered” error message, with images appearing as generic document icons rather than proper previews.
This issue affects a significant portion of the user base and remains unacknowledged by Apple’s development team. While an official patch has yet to materialize, several practical workarounds can restore functionality to your messaging workflow.
Understanding the Problem
The bug manifests specifically when users drag image files directly into Messages conversation windows. The application fails to process the image correctly, resulting in failed delivery attempts. This malfunction disrupts what should be a seamless communication experience, forcing users to seek alternative methods.
The issue appears tied to specific image formats and file locations, suggesting the problem stems from how macOS Tahoe 26.2 handles file path recognition and format processing within the Messages framework.
Solution 1: Use Keyboard Commands
Replace the drag-and-drop action with keyboard shortcuts. Select your image file, press Command+C to copy, navigate to the Messages conversation field, press Command+V to paste, then send. This method bypasses the problematic drag-and-drop handler entirely while maintaining workflow efficiency.
Solution 2: Relocate Your Files
The bug predominantly affects images stored on the Desktop. Moving your image files to alternative directories—such as Documents, Downloads, or Pictures folders—resolves the issue for most users. After relocation, the drag-and-drop function operates as intended.
Solution 3: Convert File Formats
JPG, JPEG, and PNG formats trigger this bug consistently. Converting images to HEIC format eliminates the problem. Right-click the image file, select “Convert Image,” then choose HEIC from the available options. Alternatively, WEBP format also works, though conversion requires third-party tools or web services.
Solution 4: Send Multiple Files Simultaneously
The error occurs exclusively when sending single images. Duplicating the image file and sending multiple copies together circumvents the bug. While this approach lacks elegance and may confuse recipients, it provides temporary functionality when other methods prove impractical.
Current Development Status
Apple has not publicly acknowledged this Messages application defect. No timeline exists for an official software update addressing this specific issue. Users should monitor macOS system updates and apply them promptly, as future patches may include fixes for this messaging bug.
Recommended Approach
Begin with the keyboard shortcut method, as it requires no file manipulation or conversion. If your workflow depends heavily on drag-and-drop functionality, relocating frequently-used images from the Desktop provides a more permanent solution. Format conversion serves users who prefer maintaining their current file organization structure.
These workarounds restore full messaging capability while you await an official resolution from Apple’s engineering team.