What to check on the iPhone
When an iPhone cannot send an image to Discord, check Photos access, network state, image format, and file size in that order. HEIC images and high-resolution screenshots can be larger than expected.
If size looks suspicious, use the file size limit guide to understand the boundary.
Server operators should also decide where images live
Announcement images, thumbnails, and event photos are hard to recover if they only live in chat history. A server-level storage workflow makes handoff easier for production members.
Use the same workflow for videos and large assets
If your server also shares videos, combine this with the video upload guide and the large file sharing guide to create a consistent rule.