Field Note - Obsidian Sync on Orgo VMs

Sharing this because it cost me more troubleshooting time than it should have, and it might save someone else the same rabbit hole.

In my setup, I’m using a local Hermes/Merlin agent as my main assistant, and an Orgo VM as a secondary remote agent/computer. I’m using Obsidian Sync so the VM agent can access the same context vault.

The simple lesson: The Orgo VM is its own computer. That means if Obsidian is installed on the VM, it has its own Obsidian app, its own local copy of the vault, and its own Sync settings. It is not automatically “looking through” to the Obsidian app that is open on your laptop.

What tripped me up was that everything looked connected: - same Obsidian account - same remote vault - same vault name - regular markdown notes were syncing …but some support files still weren’t showing up on the VM.

There were two things to remember.

First, Obsidian has to actually be running on the VM for Obsidian Sync to keep that VM’s local vault up to date. If the VM restarts and Obsidian doesn’t reopen, the vault on the VM can fall behind even though your laptop vault is perfectly current. So if your agent relies on Obsidian as a context vault, make sure Obsidian starts again after a VM reboot.

Second, check this setting on the VM too: Settings → Sync → Selective Sync → Sync all other types In my case, this was turned on locally, but turned off on the VM. That meant normal notes synced, but non-note support files did not.

Quick checklist before you spend hours debugging:

- Are you signed into the same Obsidian account on the VM?

- Is the VM connected to the correct remote vault?

- Is Obsidian actually open/running on the VM?

- Does Sync say fully synced?

- Are any folders excluded?

- Is Sync all other types turned on?

- If the VM restarts, does Obsidian reopen automatically?

This may not apply exactly if your whole setup lives inside the VM, but the mental model still matters:

A VM is a real computer. Apps inside it need to be opened, configured, synced, and restarted just like apps on your laptop.

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Field Note - Obsidian Sync on Orgo VMs