Steps to reproduce
On Windows desktop Obsidian (latest version), create a new note called:
sync-test.md
Paste an image into the note using clipboard paste.
This generates:
![[Pasted image 20260303233404.png]]
Confirm the image file exists physically inside the vault directory:
C:\Users\Documents\Obsidian Vault
(File size ~100 KB)
Wait for Obsidian Sync on desktop to complete.
On Linux server running headless client:
cd /opt/obsidian-vault
ob sync
Search for the image file:
find /opt/obsidian-vault -name “Pasted image 20260303233404.png”
Result:
No results.
The markdown file syncs, but the image attachment does not.
Did you follow the troubleshooting guide? [Y/N] Yes
Expected result
After running:
ob sync
The image attachment file should appear somewhere inside:
/opt/obsidian-vault
Actual result
Markdown note syncs successfully.
PDF attachments sync successfully.
Image attachments do not download to the headless vault.
Environment
Server:
Linux
Headless Obsidian Sync client (ob)
Vault path: /opt/obsidian-vault
Desktop:
Windows
Latest Obsidian version
Vault path: C:\Users\Documents\Obsidian Vault
ob sync-config:
Vault: Default Vault (…)
Location: /opt/obsidian-vault
Sync mode: bidirectional
Conflict strategy: merge
File types: image, audio, pdf, video
Configs: none
Additional information
The same vault syncs correctly between multiple desktop devices, including image attachments.
Issue appears specific to the headless ob client.
Reproducible with a brand-new test note and newly pasted image.