[Bug]: Open with AI feature not always working with Claude app on MacOS

[chandrab]

Preflight

• I searched existing issues and this isn't a duplicate
• I'm on the latest version (or I've noted my version below)

What happened?

Using the "Open with AI" feature no longer works (worked first time)

The ability to open the OK document with claude side by side is brilliant.
I also have OpenAI Codex installed -- is there a way to select which one to utilize (feature request?)

MacBook Pro M3. MacOS 26.5.1
Claude Code version 1.1596.2.1

Steps to reproduce

1. Opens Claude code correctly.

2. OK Enters this in the Claude command line
   This is an OpenKnowledge project: load the open-knowledge skill and use the OpenKnowledge MCP tools for all markdown — don't probe for .ok/ or use native file tools on .md / .mdx. Let's work on Prompting Techniques.md using OpenKnowledge. Open the OK editor in web view.

3. I have to press ENTER for it to continue (not sure if this is correct behavior or it should automatically continue)

4. Claude does a few things, says it used 3 tools and returns this:
   Found it. No browser-navigation tool or preview_* tool is available in this session, and we're on the CLI track — let me check if ok is on PATH to open it properly.

5. The first time I installed this it worked great, rebooted and not working any longer

The side by side of web view and claude is brilliant.
Claude in the bash shell instead did "ok open "Prompting Techniques" which is not as optimal.

When it worked correctly, the final bash shell was (from Claude)
Used open-knowledge: Preview url
document: Prompting Techniques
{"text":"Preview URL: http://localhost:53562/#/Prompting%20Techniques","url":"http://localhost:53562/#/Prompting%20Techniques","baseUrl":"http://localhost:53562","running":true,"autoOpen":true}
Opened OK preview in default browser
$ open "http://localhost:53562/#/Prompting%20Techniques"

(Bash completed with no output)

Platform

macOS (Apple Silicon)

How did you install OpenKnowledge?

Desktop app (DMG)

Version

0.19.2

Logs, errors, or screenshots

Additional:

Work around found/Clue of what's happening.
In step #2 above it enters that string into the Claude Command line...if I hit - it works successfully and open the OK editing pane.

Claude says this about Command-Enter.
In the Claude Code app on Mac, Cmd+Enter sends the message while inserting a newline behavior varies by context — but the common convention is: plain Enter submits, and Cmd+Enter (or Shift+Enter) inserts a newline without submitting in the prompt input box.

[tim-inkeep]

hi @chandrab, thanks for the writeup, the cmd+return note actually helps. three separate things going on here:

codex/claude picker — already there. "Open with AI" pops a menu of whatever agents you have installed (claude, codex, cursor, opencode). if you're not seeing it, update to latest.

side-by-side vs ok open — the browser side-by-side needs OK's preview server already running. your working log shows it was ("running":true, port 53562) so claude just opened that url. after a reboot if nothing's serving the preview, claude-as-CLI has no preview pane so it falls back to ok open, which just pops the OK desktop app instead of the browser. so not really broken, just the fallback. latest auto-starts the preview backend on demand which should make this way more consistent — please update and retry.

couple things that'd help when it's in the bad state:

• was the OK desktop app actually running?
• what does /mcp show in that claude session — is open-knowledge connected?

having to hit enter — we just open claude with the prompt prefilled, the app decides whether to submit, not us. plain enter should send it; the cmd+return thing is claude code's input handling. will see if there's a cleaner handoff that skips the manual enter.

lmk on the two questions above 🙏