Which chats can I add attachments to?

Messages chats, on any gray Attachment unavailable box. Chats from screenshots or Scroll Capture, on any message without a file. WhatsApp chats bring their own files.

I see Couldn't add this attachment. Try again.

Tap the add button and pick the file again. If it keeps failing, close the chat, open it again, and try once more.

Does removing it delete my photo?

No. Your photo stays in Photos or Files. Only the link in TextPort goes away.

How to add a missing attachment by hand

You will put the right photo or file back on a message in your chat.

iPhone 6 steps · Updated Sep 25, 2026

What you need

✓TextPort on your iPhone
✓A saved chat with a missing photo or file
✓The photo in Photos, or the file in Files

Sometimes a photo does not come along with a chat. If you still have it, you can add it back to the right message.

Steps

1

Find the message

Open the chat. Find the message that needs the photo. In a Messages chat, it is a gray box that says Attachment unavailable.
2

Long press the message

Press and hold the message for one second. A menu appears.
3

Tap the add button

On a gray box, tap Manually add attachment. In a chat from screenshots or Scroll Capture, tap Add attachment.
4

Pick where the file is

The Add attachment sheet shows the message. Tap Add from Photos (1) for a photo or video. Tap Add from Files (2) for a file saved in Files.
5

Tap the file

Find the right photo or file. Tap it once.
6

Wait

The sheet says Saving attachment…. Then it closes. The photo shows in the message.

Done

The message has its photo or file again. You see it right in the chat.

Tips

In a Messages chat, try the gray box first. Tap it. If you see Try Again, tap that. It asks Messages for the file again.
Picked the wrong one? Long press the message. Tap Edit attachment. Tap Replace from Photos or Replace from Files.
To take it off, tap Edit attachment, then Remove attachment. The message stays.
Files you add stay on this iPhone.

Questions

: Messages chats, on any gray Attachment unavailable box. Chats from screenshots or Scroll Capture, on any message without a file. WhatsApp chats bring their own files.
: Tap the add button and pick the file again. If it keeps failing, close the chat, open it again, and try once more.
: No. Your photo stays in Photos or Files. Only the link in TextPort goes away.