Troubleshooting

Every way Pomeroy can appear not to work, and the fix: missing tools, an app switched off, the weekly allowance, weather, updates and permissions.

Start here. Almost everything falls into one of the first three sections.

An assistant cannot see the tools

The most common problem, and almost always the least interesting cause.

1. Restart the assistant, properly

   Most assistants read their server list at launch. Quit it fully and open it again; on a Mac that means Quit, not closing the window. Claude Code and goose need a new session rather than a restart.

   Which assistants need what

2. Check Pomeroy is running

   Look for the tree icon in your menu bar. If it is missing, open Pomeroy from Applications.

   Pomeroy does not need to be running for a tool call to work, because the pipe launches it. But if it will not start, nothing else will either.

3. Check the assistant is actually configured

   Open the Pomeroy panel and look at your assistant’s row. If it does not show as set up, press Set up again; it is safe to run any number of times.

4. Check the path

   If your assistant reports that the server failed to start, it could not run the command. The path must match where Pomeroy actually lives:

   /Applications/Pomeroy.app/Contents/MacOS/pomeroy-mcp
   

   Keeping Pomeroy somewhere else changes it. The Pomeroy panel always shows the right one for your Mac, so copy it from there.

An app is switched off in Pomeroy

This is not an error. It is Pomeroy working: you asked about an app whose toggle is off, and the refusal was returned instead of your data.

Click the menu-bar icon, choose Settings, switch the app on, and ask again. No restart is needed. The tool list has not changed, only whether the call gets through.

If macOS then asks for permission, that is the grant being requested for the first time. Toggles and grants are two different things.

The weekly allowance ran out

Every tool answers with a message saying the allowance is used up and when it refills. Nothing is broken and nothing is lost.

• Checking is always free: ask “how much of my Pomeroy allowance is left?”
• The count refills a week after the current window started.
• $19 once removes the limit. Buy and activate

Changing your Mac’s date will not refill it: the meter uses a clock that no setting can move. Why

An app returns nothing, or an error

Mail: a content search finds nothing

Body search runs against an index Pomeroy builds on your Mac, and the first build takes a while on a large mailbox. Every content answer says how much of your mail the index covered and how old it is, so “nothing found” may mean “nothing in the part indexed so far”.

Ask the assistant to build the mail index, wait for it, and search again. How the index works

Weather returns nothing at all

WeatherKit checks the app’s signature against a paid Apple developer team, and refuses builds it does not recognise. A release from pomeroy.app is signed; a local build is not.

There is deliberately no third-party fallback. One would send your questions somewhere the pledge page does not name. Why

Messages: a new message is missing

Pomeroy reads the database the Messages app writes to. A message it has only just written can take a moment to appear. Wait and ask again.

Messages: it says it cannot read the database

The read-only bookmark to chat.db has been lost, usually after a macOS upgrade or a migration. Switch Messages off and on again in Settings, and hand over the file when the dialog opens.

Pomeroy proves this grant by resolving the bookmark and opening the file each time, rather than remembering that you once granted it. That is why it notices.

Shortcuts: it says the name did not match

shortcuts_run needs the name character for character. A near miss runs nothing and lists the candidates instead of guessing. Pick the exact one from that list.

Calendar or Reminders: permission was granted but it still fails

On recent macOS, agreeing to the prompt is not sufficient on its own. The app also needs a matching entitlement, and a build without one is refused even after you say yes. A release from pomeroy.app has them. The five entitlements

Permissions

macOS never asked me for permission

Pomeroy asks only at the moment you switch an app on, and only for that app. If you have already answered once, macOS does not ask again. Check System Settings → Privacy & Security for the current answer.

Maps and Weather never prompt: MapKit and WeatherKit answer any app, so the toggle is the whole gate.

I said no and want to change my mind

macOS owns that answer. Open System Settings → Privacy & Security, find the relevant list, and allow Pomeroy. Pomeroy reads grants live and never caches them, so it notices immediately.

I was asked three times for Mail, Notes and Shortcuts

Correct. Automation is asked for per app, so approving Mail says nothing about Notes.

Pomeroy is not in the Accessibility list

It never will be. Accessibility and Screen Recording are the two grants Pomeroy will never ask for, and its absence from those lists is something you can verify in five seconds. Why

Updates and the app itself

macOS says Pomeroy cannot be opened

Pomeroy is signed and notarised by Apple, so this usually means the download did not finish. Delete it and download it again.

Updates are not arriving

Check Settings → General → Keep Pomeroy up to date. If it is off, Pomeroy never asks, which is the switch working as intended.

Every update is signed, and one whose signature does not match the bytes is thrown away rather than installed.

The Claude extension disappeared

Claude Desktop occasionally loses an extension after a major update. Press Set up in the Pomeroy panel again. It is safe to run any number of times. Setting up Claude Desktop

Still stuck

Email [e-mail]. Saying which assistant, which app, and what the assistant reported back gets to an answer fastest.