Sync images between Macs: picture content or the original file

Sync images between Macs straight into a document

Both Macs should be on macOS 14 or later and in the same trusted Deskferry group, joined over a LAN where each one can find the other. Turn sync on and allow image content at both ends.

1. In the source app, use Copy Image, or whichever command copies the picture itself rather than a reference to it.
2. On the other Mac, open a document or editor that accepts pasted pictures.
3. Click where the picture belongs, press Command-V, then check that the image you meant to send is the one that appeared.

Hand over the original in Finder

When the item is a file — Cover.heic, or a PNG that belongs in a project directory — select it in Finder, copy, and paste into a Finder folder on the other Mac. That is a file transfer, with everything that implies: the group administrator needs Pro or Max, folders need Max, and the content switches and size settings at both ends still apply.

One label that confuses people: an image file can show up under Image in history. That describes the content, not the entitlement, so copying the Finder file still follows the file rules. The file handoff guide has the full sequence, including opening the received file at the destination to confirm it arrived.

Use history to pick the right picture

After copying several candidates in a row, open History, filter to Image, and let the thumbnails tell them apart. For an image file you can also search its name — search covers the records this Mac still retains, on every plan. On Free, full viewing and copying reach the global latest 20 records across all types, so an older picture can stay perfectly recognisable in a restricted preview without opening in full.

When the picture does not turn up

Paste into an image-capable app on the source Mac first, to prove that a picture — and not a link to one — is actually on the clipboard. Then check that the destination app accepts images at all. Then look at the image and file switches in Deskferry. Files also have to be fully downloaded, readable, and inside the configured total size.

If plain text fails as well, the connection is your suspect and not the picture, so go back to connection troubleshooting. There is no reason to rebuild a group because one destination app refused a paste.

A quick way to separate the two causes: use the same picture twice. Paste it into an image-capable document on the source Mac, then into one on the receiving Mac. If it fails locally, change the source command from copying the address to copying the image. If it works locally but not across the group, send a fresh sentence through first — that tells you whether to look at image handling or at the connection before you retry a large asset.