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BreakPoint - How To Guide

Getting Started

Prerequisites

  • macOS
  • Ollama installed and running
  • Pieces OS running on the configured base URL

Install Ollama

brew install ollama
ollama pull llama3.2
ollama serve

Launch BreakPoint

  1. Open BreakPoint.app
  2. Look for the icon in the menu bar
  3. No Dock icon appears because BreakPoint runs as a menu bar utility

Pre-Notarization Permissions Check

Before notarization and release testing, verify these macOS permissions on a clean machine:

  • Screen Recording for screenshot OCR and screen context capture
  • Automation for Apple Notes export
  • Accessibility if macOS prompts for control of Notes/System Events during Notes export

Triggering Doom's Moment

Option A: Left-click

Fastest way to trigger generation.

Option B: Global hotkey

Press Cmd + Shift + Escape from anywhere.

Option C: Right-click menu

Right-click the menu bar icon and choose Doom's Moment.

What Happens During Generation

  1. The menu bar icon switches into the animated thinking state
  2. The popover shows Generating... in pink with the app icon
  3. BreakPoint gathers screen and context data
  4. BreakPoint attempts generation through Pieces QGPT first
  5. If Pieces QGPT is unavailable or slow, it falls back to Ollama
  6. Export runs according to the selected preset
  7. Success or error state is shown in the popover

If a file export is included, the success message now includes the save location more explicitly.

Export Presets

Set the export destination from Properties.

Available presets:

  • File
  • Notes
  • File + Notes

File

Writes a .md file only.

Notes

Creates an Apple Note only.

File + Notes

Writes the .md file and also creates the Apple Note.

Current file location

In the current app setup, generated Markdown files are being saved to:

  • /Users/kika_hub/Documents/dooms

Example filename:

  • DoomsMoment_2026-03-27_17-21-59.md

Choosing a Generation Mode

Open Properties from the right-click menu and choose one of these:

Normal

Use for balanced, general-purpose context preservation.

ADHD

Use when you want short, scannable re-entry notes.

Code Mode

Use during development sessions when you want code-aware output.

Extra

Use when you want the most detailed handoff without code-heavy formatting.

Extra is designed to produce stronger Markdown structure, including:

  • executive summary
  • active projects
  • grouped priorities
  • decisions, risks, and open loops
  • resume plan
  • learn and explore
  • hashtags

Using the Right-Click Menu

The right-click menu includes:

  • mode label
  • export label
  • Pieces status
  • Doom's Moment
  • Open Latest Doom's Moment
  • Reveal Export Folder
  • Open Doom Moments in Notes
  • Copy Last Output Path
  • Properties
  • Close App

Notes:

  • latest-file actions are disabled if the current export preset does not include file output
  • the context menu is isolated from the status popover to avoid old popup races

Configuring Settings

Open Properties from the right-click menu.

Change Export Preset

  1. Open Properties
  2. Find the Export picker
  3. Choose File, Notes, or File + Notes

Change Export Folder

  1. Open Properties
  2. Edit Export Folder or click Browse
  3. Choose the target directory

Configure Ollama

  1. Set the base URL
  2. Use the model dropdown to pick from available models
  3. Click Refresh Models if you changed the Ollama instance or just pulled a new model
  4. Click Test Connectivity

Configure Pieces OS

  1. Start Pieces OS
  2. Set the Pieces base URL if it is not http://localhost:39300
  3. Enable Use Pieces for Doom's Moment generation
  4. Test the connection from Properties

Add Search Tags

  1. Open Properties
  2. Find Search Tags
  3. Enter comma-separated tags like work, client-a, follow-up
  4. Generate a new Doom's Moment

These tags are sanitized into hashtags and added to the generated ## Hashtags section in both Markdown files and Apple Notes exports.

Reading the Result

Markdown file

Open the saved .md file from the export folder.

Apple Notes

Use Open Doom Moments in Notes from the right-click menu, or open Notes manually.

Re-entry flow

  1. open the latest generated file or note
  2. scan the priorities and active projects
  3. use the resume plan to get back into the work quickly

Troubleshooting

It says it failed, but I expected a file

Check the selected export preset first.

  • Notes does not create a file
  • File and File + Notes do

I can't find the file

Use:

  • Reveal Export Folder
  • Open Latest Doom's Moment
  • Copy Last Output Path

Notes export failed

  • check Automation permissions for Notes
  • ensure Notes can be controlled by BreakPoint

Menu bar icon not visible

  • check menu bar overflow
  • use Cmd + Shift + Escape as fallback

Pieces OS not connecting

  • ensure Pieces OS is running
  • verify the configured Pieces base URL
  • test from Properties

OCR not capturing text

  • check Screen Recording permission in macOS Privacy settings

Generation takes too long

  • try a faster Ollama model from the dropdown if you are using a large cloud model
  • use File export temporarily if you want to rule out Apple Notes automation delays
  • confirm Pieces and Ollama both pass their test buttons in Properties

Keyboard Shortcuts

Shortcut Action
Cmd + Shift + Escape Trigger Doom's Moment
Left-click menu bar icon Trigger Doom's Moment
Right-click menu bar icon Open context menu