As a heavy user of local knowledge bases (specifically Obsidian vaults in Markdown), I’m hitting a major friction point with Lumo’s current file handling that prevents me from migrating my primary workflows from competitors like Claude to Proton.

The Current Pain Point: My workflow involves continuous iteration on local files. Currently, the loop is broken and manual:

• Upload: I upload a file to a chat/project.
• Edit: I edit the file locally in my editor.
• Sync Failure: The changes aren't reflected in Lumo.
• Clunky Re-upload: To update context, I must manually re-upload. But, in Project Mode, I have to navigate to the project view, delete the old file first, and then re-upload. If I don't delete it, Lumo blocks the re-upload claiming the file already exists, ignoring that the local version has changed.

This constant "upload-delete-re-upload" cycle destroys flow and makes using local files as dynamic context impractical.

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Proposed Implementation (Phased Approach)

Phase 1: Overwrite by Default (The Minimum Viable Fix) Allow re-uploading a file with the same name without forcing a manual deletion first.

• Mechanism: Simply prompt: "File 'X' exists. Replace with new version?"
• Benefit: Removes the tedious "delete-then-upload" step in Project views.

Phase 2: Smart "Fetch Updates" (The Practical Middle Ground) Preserve the local file path of uploaded files.

• Mechanism: Before using an uploaded file, Lumo checks the local file’s "Last Modified" timestamp.
• Action: If the local file is newer, prompt: "Local file has changed. Update context?" One click to refresh.
• Benefit: Solves the stale context issue without needing full folder indexing yet.

Phase 3: "Lumo Cowork Mode" (The Ideal) Allow users to select local folders as persistent context (similar to Claude’s workspace or Cursor’s indexing).

• How it works: Lumo indexes the folder. When I ask a question, it reads the latest local state.
• Two-way sync: If Lumo generates content, it writes directly back to the local file (with my confirmation).
• Benefit: Eliminates all upload friction. My Obsidian vault becomes a live, private context window. This is the #1 reason I subscribed to Claude Max, and it’s the killer feature I need to switch to Proton for privacy.

Why This Matters for Proton: I want to move my personal knowledge work to Proton specifically for zero-access encryption and privacy. However, the current file workflow is too clumsy compared to non-encrypted alternatives. If Lumo can handle local files as a seamless, two-way context layer, it becomes the only viable private AI assistant for power users managing local data.

Let’s bridge the gap between "secure chat" and "secure productivity.” :D