AppAddict

Cron Was Made for Always-On Unix Servers

Early in my career, I used to get annoyed when the old hands would wave away every automation problem with, “Just make a cron job.”

Cron dates back to the earliest days of Unix. It’s simple, dumb, and dependable: once a minute it checks a text file, and if a line in that file matches the current time, it runs the associated command. Like most Unix tools, it works great–once you learn the arcane scheduling syntax.

For example:

0 3 * * * /Users/amerpie/scripts/backup.sh

To cron, that means: run this script every day at 3:00 AM.**

Cron was designed for machines that live in server rooms–powered on 24/7, connected to stable networks, and rarely put to sleep.

macOS laptops are… not that.

The core problem is that cron has zero situational awareness. It doesn’t know or care whether:

• you're logged in
• the network is available
• the laptop is asleep
• macOS has changed anything since 1993
• modern features like sandboxing, power-saving modes, or System Integrity Protection exist

Cron just runs on schedule. If your Mac is asleep at 3:00 AM, tough luck. That limitation makes cron a poor fit for most real-world Mac automation.

That's Why We Have launchd

Apple introduced launchd over 20 years ago with OS X 10.4 (Tiger) to replace cron and a pile of other legacy services.

Unlike cron, launchd actually understands the modern Mac environment. It can handle:

• starting and stopping apps
• running background tasks
• scheduling jobs
• managing daemons
• responding to system events

Most importantly, launchd isn’t limited to “run at this time.” It can trigger jobs based on state and context, including:

• specific times or intervals
• system boot
• user login
• file or folder changes
• network availability
• hardware events
• on-demand conditions

In other words, launchd is designed for the messy, mobile, power-managed world Macs actually live in.

There’s just one big catch.

You don’t create launchd jobs with a simple line of text. Instead, you have to write XML property list files–verbose, picky, easy to mess up, and filled with cryptic keys you’re expected to understand.

For most sane people, that’s a hard pass.

Useful Third-Party Apps That Make This Easy

Fortunately, it’s 2026, and no one needs to hand-craft launchd XML files anymore. Several excellent Mac apps provide friendly interfaces for building launchd jobs or similar scheduled tasks.

Lingon Pro

Lingon has been around for more than two decades, and it’s still one of the best launchd tools available.

It gives you a clean GUI for creating complex jobs that can run:

• whether your Mac is awake or asleep
• whether you're logged in or not
• with root privileges if necessary
• with "keep alive" rules that automatically restart crashed processes

If you need serious, reliable background automation on macOS, Lingon Pro is the gold standard.

Price: $23.99 one-time, or $11.99/year subscription

Trial: Full-featured one-week trial LaunchD Task Scheduler

This is a simpler, cheaper alternative to Lingon Pro. It doesn’t have quite the same depth, but it’s more than enough for many users.

Key features:

• Create, edit, and delete launchd tasks
• Run jobs at intervals or on schedules (daily, weekly, monthly)
• Trigger tasks based on events like:
  • volume mounting
  • user login
  • folder changes
• Keep tasks running and auto-restart if they crash

If you want basic launchd automation without a learning curve, this $4.99 app is a solid value.

Keyboard Maestro

Keyboard Maestro isn’t primarily a scheduler–but it does include powerful time-based and event-based triggers.

Some of the available triggers:

• Hot keys
• App launch / quit / activate / deactivate
• Window events
• Clipboard changes
• Specific times or intervals
• Typed strings
• USB device events
• Public web URLs
• MIDI input
• Device connection/disconnection
• Login
• Network changes

The downside: Keyboard Maestro only works when:

• you're logged in
• the Mac is awake
• the Keyboard Maestro Engine is running

So it’s not a replacement for launchd. But for user-level automation, it’s incredibly powerful.

For example, I have a macro that periodically checks whether Raycast, Hazel, Stream Deck, and BetterTouchTool are running–and restarts them if they’re not. That’s the kind of practical glue automation Keyboard Maestro excels at.

Apple Shortcuts

Shortcuts on macOS has matured a lot, especially since macOS Tahoe. It now supports time-based automations similar to what iOS users have had for years.

But there are important limitations:

• You must be logged in
• The Mac must be awake
• It's better suited to workflows than true background services

Still, Shortcuts can trigger actions based on:

• specific apps
• power conditions
• hardware connections
• network changes
• file system events
• Bluetooth devices
• time of day

If you have an always-on Mac mini or studio, Shortcuts can be surprisingly capable. On a sleeping laptop, not so much.

More Apps with Time-Based or Event Triggers

If you just need “run this thing on a schedule” without diving into launchd, these are worth a look:

• Task Till Dawn -- Free automation tool for file management, printing, and browser tasks
• Alarm Clock Pro -- Far more than an alarm clock; great for scheduled app launching and scripts
• Shortery -- Adds real triggers to Apple Shortcuts (Wi-Fi, calendar, time, etc.)
• Scheduler for Mac -- Lightweight app and script scheduler
• Automator + Calendar Alerts -- Built-in macOS trick: create an Automator workflow, then have Calendar open it at a specific time
• Launch Control -- A high-end launchd GUI similar to Lingon Pro, but pricier

Bottom Line

If you’re automating a real Mac–not a headless server, cron is usually the wrong tool.

For anything that needs to run reliably in the background, use launchd. And unless you genuinely enjoy editing XML by hand, use a GUI tool like Lingon Pro or LaunchD Task Scheduler to manage it.

For user-level automations while you’re actively working, Keyboard Maestro and Shortcuts are fantastic.

Pick the right tool for the job, and your automations will actually work when you need them–rather than silently failing at 3:00 AM while your Mac sleeps peacefully on the nightstand.

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I've used the bookmark service Raindrop.io (and its apps for macOS and iOS as well as the Safari extension) the last three years, and it's a subscription I don't hesitate to renew. It has a deep feature set, and today it added something genuinely interesting for Pro users: a beta version of a private LLM assistant called Stella.

Stella is designed for people with large, messy bookmark libraries. Instead of manually cleaning and reorganizing, you can just ask for help in plain language. Examples the system already understands:

• Organize my unsorted bookmarks into collections
• Suggest a better structure for my library
• Find articles about Formula 1 and tag them by team
• Find everything about Japan and move it to Travel
• Clean up my tags--merge duplicates like "recipe" and "recipes"
• Find broken links
• Show duplicate bookmarks

The key detail I appreciate: Stella only suggests changes. You review and approve everything before anything is actually modified.

What you get for free

The free tier of Raindrop.io is surprisingly generous and will be more than enough for a lot of users:

• Import bookmarks from other services and browsers
• Unlimited bookmarks
• Unlimited collections
• Unlimited highlights
• Unlimited devices
• More than 2,600 integrations via IFTTT
• Apps for macOS, iOS, Android, Chrome, Safari, Firefox, and Edge

For a no-cost service, that’s a serious toolkit.

Why I actually use it

One of my favorite parts of Raindrop is how well it fits into a real Mac workflow. The Raycast integration is excellent: I can type “rd,” hit Enter, and instantly search my entire collection of 2,800+ bookmarks.

Raindrop supports both folders and tags, and I use both heavily. The iOS share sheet is just as smooth as the browser extension, and both let me add notes to anything I save. I can highlight passages directly in the app, and there’s a free Obsidian plugin that keeps everything in sync with my notes.

A feature that sold me on Pro early on is the permanent library. Raindrop saves a copy of every bookmarked page on its servers, so if a site disappears, I still have the content. That alone is worth a couple bucks a month.

It also handles PDFs well. Pro users can upload documents and access them from any device, but even free users get 100 MB of PDF uploads per month.

I’ve tied Raindrop into the rest of my information flow, too. Using IFTTT, anything I star in Inoreader automatically lands in Raindrop. I do the same with YouTube–every video I like gets saved as a bookmark. It quietly becomes a personal knowledge hub without much effort.

The Pro plan

If you want more than the free tier, the Pro plan runs $2.99 a month or $28 a year, which feels reasonable for what you get.

Pro includes:

• Everything in the free plan
• AI suggestions for folders and tags
• Full-text search across saved pages
• Permanent library copies of pages
• Reminders to review saved items
• Annotations
• Duplicate and broken link finder
• Daily backups
• Upload up to 10 GB of files per month
• Priority email support
• Access across all platforms

Raindrop.io has quietly become one of those “set it up once and rely on it forever” tools in my stack. If you’ve got years of bookmarks scattered across browsers and services, it’s one of the few apps that can actually help you make sense of them instead of just giving you another pile to manage.

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It's a given that we all need a safe place to store or back up our digital lives--somewhere our data will survive if a laptop gets stolen or a house burns down. Beyond simple protection, there's the everyday convenience of being able to reach your files from any device, anywhere with an internet connection. For most of us, that means choosing a cloud service that fits our needs. The usual suspects are U.S.-based: iCloud, Google Drive, Dropbox, and plenty of others.

---

In 2025, I decided to rethink that default. For privacy reasons, I wanted to reduce my reliance on U.S.-based cloud providers and move toward services located in countries with stronger data-protection laws. One of the companies I landed on was Koofr, which is based in Slovenia and operates under EU privacy regulations. After more than a decade of paying monthly fees to Google and Dropbox, I found a lifetime deal for 1 TB of Koofr storage on StackSocial (still available) and bought it immediately.

---

Koofr’s privacy story is refreshingly straightforward. Files are protected with strong encryption, there’s no ad tracking, no content scanning, and no behind-the-scenes data harvesting. Because Koofr operates under EU data-protection standards–currently some of the strictest in the world–your personal data is treated as exactly that: yours.

---

Koofr has a long feature list, and I covered it in detail when I first migrated. If you want the full breakdown, you can read that here. The short version:

• You can connect multiple cloud accounts (Dropbox, Google Drive, OneDrive) and search across all of them from a single interface.
• It includes in-browser Office support for editing Word, Excel, and PowerPoint files.
• File sharing is flexible, with expiring or permanent links, public receive links, and no hard restrictions on file size or type.
• It works everywhere: web, desktop apps, mobile apps, and even through WebDAV or rclone if you want to integrate it with other tools.

---

Moving my data over was painless. From the Koofr web interface, you can mount other major cloud services and simply drag files from one to another. If you prefer command-line tools, those work just as well.

---

There are several ways to access Koofr from a Mac. You don’t technically need any special software–macOS Finder can mount WebDAV drives, and Koofr supports that natively. Apps like QSpace Pro can maintain a persistent connection and automatically mount Koofr at startup. For my own workflow, though, I prefer the official Koofr desktop app. It’s faster than plain WebDAV and adds useful features I rely on.

---

One feature I didn’t expect to love is Koofr’s local shared folders. You can create shared spaces between computers on your home network where the data never leaves your LAN. It has quietly become my favorite way to move files between my Macs.

In the ten months I’ve been using Koofr, I haven’t experienced a single outage that affected me. Just as important, they don’t bombard me with upsell attempts or marketing emails–something that feels almost unheard of in the tech space these days.

At this point I’m syncing a lot of my digital life to Koofr: my personal music library, ebook and audiobook collections, software archives, important documents, and roughly 75,000 photos. I even managed to accidentally delete a large batch of files through the web interface. Thanks to Koofr’s restore tools, I recovered everything without having to re-upload a thing.

---

The main criticism you’ll see online is speed–specifically that Koofr can feel slower than the big U.S. providers. I can’t really speak to that. For my needs, performance has been perfectly fine, and I’ve never found myself waiting around wishing it were faster. I’m not a heavy user of the iOS app, but some people do wish it were as polished and feature-rich as the Dropbox or Google Drive mobile apps.

---

Who Koofr Is (and Isn’t) For

If your top priorities are privacy, straightforward pricing, and reliable cross-platform file storage, Koofr is an excellent choice. It’s especially appealing if you like having multiple ways to access your data–native apps, WebDAV, rclone, or even direct browser access–without being locked into a single ecosystem.

---

It’s also a great fit for people who want to break free from the endless subscription treadmill. The lifetime plans make financial sense if you plan to keep your data around for years, and Koofr has been around long enough to feel stable and mature rather than fly-by-night.

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On the other hand, Koofr probably isn’t ideal if you live entirely inside Apple’s ecosystem and depend heavily on deep iCloud integrations, or if you need ultra-fast collaboration features on par with Google Workspace. Power users who rely on tightly integrated mobile apps with every bell and whistle might find Koofr’s apps a bit more utilitarian.

---

For everyone else–especially Mac users who care more about control and privacy than about shiny extras–Koofr hits a practical sweet spot. It’s not flashy, but it’s dependable, reasonably priced, and refreshingly respectful of your data. For my workflow, that matters a lot more than another animated onboarding screen.

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The number of Mac apps you can install through the free package manager Homebrew keeps growing by the day. Tools like Cork, Taphouse, and Updatest can even convert apps you originally installed through other methods into versions that Homebrew can manage and update for you.

Homebrew also includes a built-in backup feature that creates what it calls a Brewfile–basically a plain-text script listing everything Homebrew has installed on your system. That file can later be used to reinstall your entire app catalog in one shot, which is incredibly useful if you’re setting up a new Mac or rebuilding your current one from scratch.

If you’re the kind of user who regularly tweaks your setup, experiments with new apps, and keeps everything updated, then your Brewfile needs regular backups to stay relevant. Otherwise, it quickly turns into an outdated snapshot of a system you no longer have.

The script below automates that process. It generates a fresh Brewfile on demand, places it inside a date-stamped folder, and saves it wherever you want–ideally somewhere that syncs to the cloud or another machine. You can run it manually, schedule it with cron, or trigger it through a Keyboard Maestro macro at a set time each day.

In short, it turns “I should really back up my Homebrew setup more often” into something that just happens automatically.

Important note: This script assumes you’re running an Apple Silicon Mac. If you’re on an Intel machine, you’ll need to adjust the Homebrew path, since it lives in a different location on those systems.

/usr/bin/osascript <<'APPLESCRIPT'
tell application "Terminal"
  activate
  do script "/bin/zsh -lc 'export PATH="/opt/homebrew/bin:/opt/homebrew/sbin:/usr/local/bin:$PATH"; \
set -e; \
\# Ensure Homebrew + Bundle are available
if ! command -v brew >/dev/null; then echo "Homebrew not found in PATH"; exit 1; fi; \
brew bundle --help >/dev/null 2>&1 || brew tap homebrew/bundle; \
\# Create dated folder inside an archive location
STAMP_DATE=$(date +%F); \
STAMP_TIME=$(date +%H-%M-%S); \
DEST="<PATH TO ARCHIVE LOCATION HERE>$STAMP_DATE"; \
mkdir -p "$DEST"; \
\# Filename: Brewfile-YYYY-MM-DD_HH-MM-SS
OUTFILE="$DEST/Brewfile-${STAMP_DATE}_${STAMP_TIME}"; \
\# Dump Brewfile there
brew bundle dump --file="$OUTFILE" --force; \
echo; echo "Brewfile saved to: $OUTFILE"; \
\# Reveal it in Finder
open -R "$OUTFILE"; \
echo; echo "✅ Done."; \
\# Keep the Terminal session open
exec $SHELL'"
end tell
APPLESCRIPT

How to use this

If you’ve never automated a Brewfile backup before, here’s the simple, practical way to put this to work:

Save the script somewhere logical.

Drop it in a folder you already use for utilities or personal scripts–something like ~/Scripts or ~/bin.

Decide where you want backups to live.

The best location is a folder that automatically syncs–iCloud Drive, Dropbox, Koofr, etc. That way you always have off-machine copies.

Run it once manually.

Open Terminal, execute the script, and confirm that it creates a dated folder containing a Brewfile exactly where you expect.

Automate it.

1. • Keyboard Maestro: Create a simple macro with a "Time of Day" trigger that runs the script every night.
   • cron/launchd: Schedule it to run daily or weekly if you prefer a pure system-level approach.
2. Test a restore someday. 

Run the script manually

The real value of a Brewfile is being able to reinstall everything with a single command. On a fresh Mac, you can just run:

brew bundle --file=YourSavedBrewfile

This whole process takes about ten minutes to set up and pays for itself the first time you migrate to a new Mac or need to rebuild your system.

If you live in Homebrew–and a lot of us do–having automated, versioned Brewfile backups is one of those small, boring habits that quietly saves a huge amount of time.

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One of the things I treasure most about being part of the community that includes independent Mac developers is the opportunity to make feature requests. I never cease to be amazed when an app I use and love gets updated to include an idea I suggested. Yesterday, for the second time, the developer of MountMate (Homie Lab) responded to a feature request within hours. Back in June, he added Intel compatibility, and yesterday he added hotkey support so that MountMate can now be used in automation workflows like Keyboard Maestro, BetterTouchTool, and Apple Shortcuts.

Additional new features include:

• Dynamic Menu Bar Icon: The menu bar icon now changes to indicate app state:
  • Shows a clock badge while mounting/unmounting drives
  • Shows a warning badge if an error occurs
  • Returns to normal when operations complete
• Better Mount/Unmount Icons: Changed mount/unmount button icons from arrows to plus/minus for clearer meaning.

MountMate is a menu bar app that offers levels of control over external drives through a GUI that simply aren’t included in macOS without resorting to shell commands. It includes a switch that prevents the automated mounting of connected USB drives at login, which is useful if you prefer to connect drives manually. You can selectively include or exclude specific drives from this rule, a handy option if you use a USB drive for Time Machine.

I used to plug in external drives and just leave them mounted, but over time I found that doing so could cause slowdowns and occasional problems, particularly with Finder extensions. These days I prefer to keep drives unmounted unless I have a specific reason to use them.

With MountMate, if you have drives that contain multiple partitions, you can selectively mount only the ones you need instead of mounting everything. Now that hotkeys are available, it’s simple to create a shortcut that mounts a drive, launches an application, and then unmounts the drive after the file operation is complete. You could simplify things even further by scheduling the drive to mount at a specific time of day, running the file operations you need, and then scheduling the drive to unmount a couple of hours later. During the time it’s mounted, you can use whatever apps you like to read from or write to it.

I use Sync Folders Pro, FreeFileSync, Smart Backup, and other similar apps to copy files automatically when certain conditions occur on my Mac.

Although MountMate is primarily designed for external USB drives, it also includes the ability to mount network drives at login if you routinely connect to other computers on your network. Best of all, MountMate is donationware.

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Every night, shortly before 12:00 AM, an automation I set up on my Mac opens the ChatGPT app and send this prompt:

Generate my Obsidian AI Daily Log for the last 24 hours.

Requirements:
- Sort everything in true chronological order with timestamps.
- Use one-line summaries for each discussion.
- Structure it as a technical journal, not a chat summary.
- Include these sections:
  1) Timeline
  2) Signals & Insights (what I learned or realized)
  3) Friction & Problems (what broke, confused, or slowed things down)
  4) Decisions (explicit or implicit choices made)
  5) Open Questions (unresolved issues)
  6) Next Actions (concrete follow-ups)
  7) Backlinks (Obsidian-style [[topics]])
  8) Tags (#macos #automation #clawdbot #health etc.)

• Use Obsidian-friendly Markdown.
  - “At the end, include the full log again inside a plain-text block between ===BEGIN OBSIDIAN DAILY LOG=== and ===END OBSIDIAN DAILY LOG=== so I can save it to a file via automation. Do not use any clickable links for this block.”

When I wake up in the morning, there is a note in a folder in my vault, named using a repeatable convention so that I can create links each day in my daily note using a template with a variable.

An example note looks like this

## 🤖 AI Daily Log (23:52)

Obsidian AI Daily Log — Last 24 Hours

Timeline

-   01:02 — Generated Obsidian AI Daily Log for January 30 with full technical journal structure and export block.

-   02:44 — Investigated how the macOS utility LeaderKey works and explored command-style use cases beyond apps and URLs.

-   03:36 — Asked whether Calibre maintains logs and explored recommended settings and behavior of the Job Spy plugin.

-   04:44 — Requested a detailed narrative overview of Homeland Season 2, Episode 5.

-   07:05 — Analyzed the macOS security command sudo spctl --master-disable and its system-wide implications.

-   08:02 — Evaluated new eyeglass prescription with emphasis on computer-centric use and identified reputable online vendors.

Signals & Insights

-   LeaderKey functions best as a command dispatcher layered atop existing automation.

-   Calibre logging is present but distributed and inconsistent.

-   Disabling Gatekeeper globally is risky and best reserved for short-term diagnostics.

-   Computer-focused lenses align better with actual usage patterns.

-   Homeland continues deliberate narrative destabilization in S2E5.

Friction & Problems

-   Lack of centralized logging in Calibre complicates troubleshooting.

-   Sparse advanced documentation for LeaderKey.

-   macOS security controls encourage overcorrection due to poor visibility.

Decisions

-   Use LeaderKey selectively as automation glue.

-   Avoid permanent Gatekeeper disablement.

-   Choose computer-optimized eyewear.

-   Maintain AI logs as technical records.

Open Questions

-   Best practices for persistent Calibre job logging?

-   Community-standard LeaderKey command patterns?

-   Safer macOS security toggling workflows?

Next Actions

-   Prototype LeaderKey + shell/KM workflows.

-   Capture Calibre debug logs during test jobs.

-   Write a Gatekeeper troubleshooting checklist.

-   Order glasses optimized for screen work.

Backlinks

[[Obsidian AI Daily Log]] [[macOS Security]] [[LeaderKey]] [[Calibre]] [[Automation]] [[Homeland]] [[Health]]

Tags

#tech/macOS #tech/automation #apps/leaderkey #apps/calibre #tech/security #obsidian #entertainment/television #health #vision

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When Keyboard Maestro went on sale during the Black Friday season last year, I was surprised by the number of people who purchased the app and then found themselves at a loss for use cases. The community forum run by Peter Lewis, the developer, has a good reputation for being helpful, but in my experience it's full of complex solutions to problems I don't have.

My intention has never been to use Keyboard Maestro as a software development platform. It's always been about this simple question: how can I turn 10 clicks into 1 click--or better yet, how can I not have to click at all?

Triggers

Here's a list of some recent macOS automation patterns I've introduced into the way I use my Mac. I've been inspired by the introduction of the Extra Bar to make nested menus of related macros, and I've stopped relying on trying to remember so many finger-cramping hotkey combinations.

One of the magical things about automating with Keyboard Maestro is the sheer number of ways a macro can be triggered. My most-used triggers are:

• Time of Day triggers (do this action at this time)
• Application Launch triggers (when this app opens, do this thing)
• Periodic triggers (do this thing every X minutes)
• Good old hotkeys
• Select-from-a-menu triggers
• Login triggers (do this thing X seconds after I log in)
• Mounted Volume triggers (when this volume is mounted, do this thing)

Macros

• Keeping apps alive -- Runs every 10 minutes with a trigger of "If Raycast is not running" and an action of "Start Raycast."
• Log out cleanly -- One action quits all apps, the next pauses, then Keyboard Maestro ejects all disks and issues the logout command. This is how macOS is supposed to do it, but if you have apps that hang up your logouts or external drives that don't eject cleanly, you can insert a solution into this macro.
• Mark all mail as read -- Uses menu bar commands and simulated mouse clicks.
• Mount and unmount attached backup drives -- Keyboard Maestro runs a simple script to mount and unmount USB drives that stay physically connected but don't need to be available all the time. You can do the same with network shares. For example, when a backup or syncing app launches, the mounting script runs; when the app quits, the drive is unmounted.
• If Bloom opens, close QSpace and **If Rectangle Pro launches, quit SnapsOfApps******
• Display a list of running Dock and menu bar apps and restart (not quit) the one you click -- I like to test software and keep up with new features by running multiple apps in the same category. This keeps my MacBook from getting bogged down.
• Automatically connect via screen sharing to other Macs and Linux boxes -- Apple's built-in VNC client supports internal URLs, which Keyboard Maestro can open directly.
• Batch open URLs in a specific browser -- I use this with Firefox. The macro closes the current window and opens a new one containing only the URLs I specify.
• If Updatest opens, also open Nektony -- When testing apps, I often need them side by side. A macro is the easiest way to make that happen.
• Batch quit jobs for groups of apps -- Just as you can open a group of apps with one command, you can close them when you're done.
• Backup Homebrew -- This macro backs up my entire Homebrew configuration via a script, then copies the resulting file to a specific folder on my backup drive.
• Restart Finder -- If Finder starts misbehaving, issuing killall Finder via a hotkey is far more pleasant than hunting through Activity Monitor.
• SSH -- In a home lab environment, I use passwordless sudo and small scripts for one-click terminal access to other machines.
• Run Topgrade on a schedule with no prompts -- Topgrade updates Homebrew apps, Mac App Store apps, and various developer tools. Using a time-of-day or periodic trigger, it can run unattended.
• Upgrade Mac App Store apps (in Terminal) -- If you're tired of waiting on the App Store UI, you can install the mas CLI and trigger it via Keyboard Maestro.
• Open the App Store directly to the Updates tab -- I don't browse the App Store much. When I open it, I'm either searching or updating, and both can be automated.
• Create keyboard shortcuts for actions developers didn't assign one to -- In Calibre, my macro opens the metadata editor to the Tags field and advances to the next book during bulk edits. Neither action exists natively; I built both with Keyboard Maestro.
• Automatically query ChatGPT each night for a list of topics we discussed and copy it into Obsidian -- The macro opens a new ChatGPT conversation and pastes a reusable prompt.
• Copy selected text to Ghostty and press Return -- I couldn't get PopClip to do this, so Keyboard Maestro stepped in.
• Copy Obsidian daily notes into Day One -- Redundant, yes, but I've used Day One since 2014 and like keeping a parallel record for continuity.
• Open Dropbox briefly to download files I emailed to it -- I prefer not to stay connected to cloud services unless I need them, so a macro connects, syncs, and disconnects.
• Open a BBEdit window with the clipboard contents
• Open and close backup apps -- I use several backup tools and don't want them running constantly, so Keyboard Maestro launches them on a schedule and shuts them down afterward.
• Menu of window-layout launchers using Rectangle and SnapsOfApps -- I have too many layouts to remember their hotkeys, so Keyboard Maestro presses them for me via a menu.
• Open System Settings to frequently used panes -- Just shaving off a few more clicks.
• Keyboard shortcut to copy the URL of the current page -- It still amazes me that Vivaldi doesn't ship with this, but it took about a minute to fix with a macro.

Hopefully this gives you a few ideas with what you can do with Keyboard Maestro, removing some of the frustration and demonstrating that it's not so much an automation app but a way instead to build your personal infrastructure.

More examples - My Top 10 Keyboard Maestro Macros

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Ryan Dekker, the developer of SnapsOfApps, a robust and full-featured window management app, just released an update that adds a bevy of new features aimed at more complex setups involving multiple monitors and spaces. He tackled thorny problems like managing how macOS identifies identical display models and how using a MacBook in clamshell mode affects window management. In under 10 minutes, I was able to install and configure the app to use two displays and eight spaces, launch a dozen apps with individual windows, and have every single aspect of the setup work correctly the first time from a simple hotkey command. All of this comes from an app that costs only $6.99 and includes a seven-day free trial. It also offers a full suite of window positioning tools that rival what the big guns (e.g., Moom and Rectangle Pro) in the field can deliver.

Background

Lagging well behind Microsoft Windows, macOS did not implement a relatively complete suite of native window management features until Tahoe. Even now, the native tools still lack many features found in third-party apps, such as the ability to automatically position apps at launch and rearrange windows when displays change. You also can't trigger layouts via scripts or hotkeys.

As u/arduinoRPi4 pointed out in a recent thread, "Window and space management on macOS is a mess, especially because macOS itself doesn't expose the Spaces API, which is controlled/owned by Dock.app, and different windows send different callbacks and whatnot. [Problematic apps] use private APIs that are in this case unreliable and result in… issues…. Multi-monitor seems like an afterthought on macOS and is really poorly designed in a lot of aspects that it's laughable."

As I recently pointed out, finding a solution for managing windows and apps in a multi-monitor, multi-space macOS setup has been a challenge. I've been looking for an app that could primarily do one thing: open a collection of apps and place their windows in the desired positions, on the desired spaces, on the desired monitors.

I tested:

• Moom
• Keyboard Maestro
• Stay
• Bunch
• Spencer
• Better Touch Tool
• Elgato Stream Deck
• Raycast

It was possible to achieve my goal with Keyboard Maestro, but every single window and app had to be added one at a time, with carefully choreographed hotkeys to launch apps, change spaces, and insert delays to prevent commands from overlapping. In subsequent testing, I also found that Rectangle Pro can achieve similar results with relatively little friction.

Not everyone has complex setups--or even cares about window management. For years, I used nothing but a MacBook with its single native display and ran most of my apps in full-screen mode. But there are plenty of people with three or four displays on hyper-powerful Mac Studios and Pros who could benefit from a tool like SnapsOfApps.

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Automating repetitive tasks on my Mac has been an ongoing obsession for years. To me, it's the essence of using a computer as the tool it's meant to be. The less often I have to click the same sequence of buttons I clicked yesterday, the happier I am. To that end, I've long relied on Keyboard Maestro, BetterTouchTool, Hazel, Drafts, Apple Shortcuts, and IFTTT.

Two days ago, I read about a new agentic AI app called Clawdbot that runs locally on a Mac and interacts with it in ways previous apps simply couldn't. People have strong feelings about AI. I know I do. I'm not a fan of having my blog posts harvested for their information while never getting the chance to interact with the people who want that information. Nor do I enjoy being flooded with AI-generated content passed off as "real human" effort. But AI agents--tools that let computers do actual work for us--feel fundamentally different. They don't fit neatly into those objections.

I have a spare Mac I use for testing software, so I decided to take Clawdbot for a spin. You can also run it in a VM. Once you see what it can do, you'll understand why you need to be extremely careful about the information it can access. It was a beast to set up. The developer, Peter Steinberger, is a solo creator, not a front for a giant AI company. The product is new, and while there is documentation, it's incomplete and doesn't cover many edge cases. You can install the Mac app using Homebrew--

brew install clawdbot

--but that's only part of the story. The real power lives in the CLI, and to get that you need a package manager like Node. Run

curl -fsSL [clawd.bot/install.s...](https://clawd.bot/install.sh) | bash 

in a shell and hope your $PATH and environment don't fight back.

One of Clawdbot's most compelling features is its ability to communicate through familiar messaging apps: WhatsApp, Messages, Discord, Slack, or, in my case, Telegram. You can literally send your Mac a message and tell it to do things. It can email you files or drop copies into cloud storage on your behalf.

The intelligence behind the agent comes from whatever AI service you're authorized to use via an API key--or from a local model if you prefer. All interaction history stays on your computer, stored plainly in a folder of Markdown files. There are already plugins for Mac apps like Obsidian and Things 3, but the most intriguing piece is Peekaboo, a radical framework that can "see" your Mac's screen, understand UI elements (buttons, menus, text fields), and interact with them by scrolling, clicking, and typing. It can chain these actions together in complex ways, and all you have to do is describe what you want in plain English. In effect, you can add capabilities to software that its developer never imagined.

You can even grant Clawdbot access to your Terminal, allowing it to design and execute scripts endlessly. Unsurprisingly, this sets off alarm bells for anyone with sensitive data. I'm not a cybersecurity expert, but I've been around long enough to have a healthy respect for risk. Be careful--but if any of this sounds exciting, it's absolutely worth exploring.

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SmartTracker

SmartTracker is a universal app that syncs across all platforms via iCloud. Using the URL from a vendor's page (Newegg, Amazon, Micro Center, etc.), the app tracks prices in near real time. You can set a target price and receive a notification within minutes of a price drop.

Several features stand out: charts, tracking numerical data beyond price, and collections. When I'm shopping for a big-ticket item, I find it useful to create a collection of the same product across multiple vendors. Today I got excited when Micro Center listed Mac minis for $100 less than Amazon--until I noticed the fine print: in-store pickup only, at a single store in Georgia.

You can use the free version for up to five items. The full version costs $19.99 in the App Store. The developer, Hugo Price (u/hprione on Reddit), is responsive to support requests, bug reports, and feature suggestions.

WithAudio

WithAudio is a powerful text-to-speech application under active development, with new features and improvements arriving on a weekly basis. It currently supports English and French, with Spanish and Hindi on the roadmap for the near future.

The app works offline after a one-time download of additional resources, which happens automatically after you enter your license. In addition to choosing a language, you can select from 29 different voices across male and female options.

Using your Mac, you can process entire books, queue long documents, and export MP3 or M4B chapters to build your own audiobook library. WithAudio supports EPUB, Markdown, TXT, and some PDFs. (Pro tip: use Calibre to convert PDFs to EPUB for free.)

The Mac app also lets you follow along as a document is read, automatically scrolling and highlighting each sentence. There's even a Chrome browser extension for reading web pages.

The app is priced at $25.50 for a lifetime license and includes a seven-day, no-questions-asked refund period after purchase. Check out the developer on Reddit: u/s3rgio0

Delvepad

My background is in educational technology, primarily in the K--12 world. I always enjoy finding indie apps for students because they're often built by dedicated developers with real skill in conveying information.

Delvepad, a free and open-source app, fits that description. It's available for iPhone, iPad, and Apple Silicon Macs and is useful as a reference tool for lessons on artificial intelligence and the training of large language models. It includes a glossary and shareable resources.

Check out the developer on Reddit: u/Other_Passion_4710

Unfriction

I'm on a lifelong quest to find the perfect scratchpad. The way I work involves accumulating and processing small fragments of text throughout the day. Sometimes I need that information for two minutes; sometimes I want to keep it forever. Either way, I need a way to find it later, when future me goes looking for it with only the faintest memory of what it contains.

A good scratchpad needs to be as friction-free as possible. It should open instantly, accept information without ceremony, and then get out of the way. That's exactly what Unfriction does

It's a Mac overlay notes app by indie developer and Reddit user u/Cute-River-1592 Beyond its near-instant launch, its features include smart tags, automatic OCR from screenshots and an endless built-in clipboard manager. You can do imports and exports of your notes and choose any file storage location you want. It has a limited free version, and a lifetime license will run you $19.99. for a transferable 2-Mac license.

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I spent most of my computer using life on a Macbook and only recently started using a dual display setup. I didn’t start this process until after the release of macOS 26, Tahoe. Quite possibly, that may be the absolute worst time to be experimenting with this in the history of the Mac. This is not my favorite version of the operating system. I’ve found that some relatively common applications are resistant to window management across Spaces: Calibre, Obsidian, Better Touch Tool, System Configuration, and Elgato Stream Deck Configuration are all consistently problematic. In addition, having windows from the same application open on more than one desktop creates issues for most window-management applications. Instead of using multiple windows from one browser, I’ve found it easier to just run two different browsers.

I am 100% open to suggestions from anyone who’s been down this road before me. Tell me what apps you use and why. If you have suggestions for best practices, please pass them along. Here’s a list of the tools and applications I’m currently trying to adapt to the way I use my Mac.

Bunch

Bunch manages windows and Spaces indirectly through easy-to-use scripts. The developer, Brett Terpstra, is a Mac legend, and he very kindly helped me troubleshoot some weird problems I ran into—specifically losing the required file association to run the scripts. Imagine Word telling you it can’t open .docx files. That’s what Bunch kept doing to me.

Moom

The folks at Many Tricks are also legendary and genuinely nice. Moom is an award-winning app that lets you move and resize windows using hotkeys or menus. Theoretically, a setup like mine—two displays, twelve apps, eight Desktops—can be triggered with a single shortcut that launches everything and puts the windows exactly where I want them. I say theoretically because, with the apps I use, the results aren’t consistent, and it never gets everything right.

Spencer

Spencer doesn’t have Moom’s window-management depth. It’s designed for saving layouts for groups of Spaces/Desktops or for whatever is currently on screen across multiple displays. The developer is extremely responsive and even sent me a custom DMG that could control Calibre after learning I was having trouble with it. Unfortunately, like Moom, it doesn’t consistently place my apps and windows where I want them, so I end up making manual adjustments every time.

Snaps of Apps

The developer of Snaps of Apps is actively working on adding better Spaces support and improving responsiveness on laptops running in clamshell mode. I’ll continue testing every version he sends me.

Keyboard Maestro

This workhorse can actually do what I want, but it turns what other apps promise to do with a single click into a 50-step macro I have to build manually. That may simply be the price I have to pay to get things set up exactly the way I like them.

Better Touch Tool

For anyone fluent in Better Touch Tool’s action set, building the same kind of workflow as Keyboard Maestro is absolutely possible. It looks something like this:

• Navigate to the Space where you want to launch an app
• Insert pauses when switching Spaces
• Launch the app
• Pause
• Move the app’s window where you want it
• Pause

Elgato Stream Deck

I’m new to this gadget. It provides a physical interface that ties together Shortcuts, Keyboard Maestro macros, Moom hotkeys, and scripts of all types. There’s simply no way I can cram many more hotkeys and trackpad gestures into my brain. I’m full.

Raycast

Raycast is another daily driver with window-management capabilities. I love the “almost maximize” command and invoke it instantly whenever an app tries to force full screen on me.

Stay

Stay remembers where your app windows live and puts them back there when displays change, apps relaunch, or the system restarts. It’s a persistence tool, not a controller—you arrange things once, and Stay enforces that memory. Unfortunately, it doesn’t work consistently. It’s effectively abandonware and seems better suited for people who constantly connect and disconnect external monitors.

My Basic Stack

The mysterious and obscure stack I’m using that’s causing me all these issues (/s) is listed below, If you are interested in why I use these apps, click the links. 

• Fastmail (Display 1, Space 1)
• Mona for Mastodon (Display 2, Space 5)
• Things 3 (Display 2, Space 5)
• Messages (Display 2, Space 5)
• Obsidian (Display 1, Space 2)
• Firefox (Display 2, Space 6)
• Drafts (Display 2, Space 6)
• Calibre (Display 1, Space 3)
• QSpace Pro (Display 2, Space 7)
• Vivaldi (Display 1, Space 4)
• Ghostty (Display 2, Space 8)
• QuickGPT (Display 2, Space 8)

Background

 My career was in educational technology, and I moved from school to school with a MacBook to put out fires and manage networks. I had one 15- or 16-inch display, and that was it. Now that I’m retired and have a desk of my own—complete with two 27-inch displays—I’m trying to create some new habits. As part of that, I’m attempting to use Spaces and Desktops in my workflow for the first time.

On a laptop with a single display, I was in the habit of running every app in full-screen mode and switching back and forth as needed. Now, with all the screen real estate I have, duplicating that workflow feels absolutely wasteful.

I settled on using four desktops per display, for a total of eight. I typically run around a dozen non–menu bar applications at a time, and I change them up depending on what I’m doing. I have one set of apps I use when I’m writing, another set for media management, and a third set for experimenting with automation tools and my self-hosted server.

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When it comes to sharing data from a Mac, there are plenty of scenarios and plenty of methods. Identifying the right tool for the job comes with experience. Whatever method you land on today might not be the best method in a year--and that's OK. Sometimes a system you already know how to use and troubleshoot is better than something new and unproven, no matter how many bells and whistles it has. And then there's the gradual enshittification of tech, where the useful and free tool you once loved slowly becomes expensive and exploitative.

Regardless of circumstances, the criteria most people use to judge these tools in today's tech world are security, speed, and reliability.

My Use Cases

There isn't a one-size-fits-all solution for sharing files.

• It depends on the type of data you want to share: an image, a link, a single document, a 20 MB DMG, or an 11 GB MKV video.
• The type of device the intended recipient is using.
• The sensitivity of the information. There's a big difference between a funny meme and a copy of your tax returns.
• How soon the information needs to be available to the recipient.

Scenario 1 -- I have a link or image and I want to share it RIGHT NOW to the iPhone, iPad, Windows laptop, or MacBook my partner is using.

If you're going from one Apple device to another, built-in tools like AirDrop, Messages, or email are all viable options, with AirDrop being the flakiest. That's usually because both sender and recipient need the correct settings, and the recipient has to be savvy enough to know where the received file ended up on their device.

If you're sharing with a Windows or Android user, a cross-platform messaging service like Signal or Telegram can work. For the tech-savvy, LocalSend is a useful app that's cross-platform, free, and powerful, with a few gotchas. It has to be running on both devices, and anyone with a complicated firewall setup may be in for a headache.

Scenario 2 -- I have several documents I want to share with my partner, who will need to download and use them on her MacBook.

When you're at home, there's no need to send the information through the internet. LocalSend is a good option. You can transfer files even if your internet connection is down.

While it's relatively easy to turn on local file sharing for Macs on the same network, it's a best practice to leave that turned off, as it opens up another attack vector for bad actors. If you resort to email, get in the habit of sending files in password-protected ZIP archives. Free tools like Keka can handle that easily. Another easy-to-use and powerful encryption tool is Encrypto.

If it better suits your purpose, most cloud services (iCloud, Dropbox, Google Drive) have Finder integration that lets you share links to files. Just make sure you know whether you're sharing a copy of a file or sharing access to the file--there is a difference.

I don't use US-based cloud storage for most of my files. The two services I do use, Koofr and kDrive, both offer sharing through links. Koofr offers lifetime access to 1 TB of storage for $139. kDrive has a 3 TB subscription plan for just €4.99 a month.

Scenario 3 -- I have a collection of documents, images, and links I want to access from my phone, iPad, and Mac, with changes made on one reflecting on the others.

This is where you need a reliable cloud service. iCloud is built in, but results can vary wildly for all sorts of reasons. Sometimes I have folders on two Macs that live about three feet apart, and they'll go days without syncing Desktop and Documents.

If you're tech-savvy, there are self-hosted options like Immich for photos and Nextcloud, a roll-your-own cloud service with many compatible apps and plugins--but did I mention that it's slow?

Scenario 4 -- I have 16,000 books, 150,000 photos, and 32,000 songs I want to continually sync between four computers on the same LAN for reasons that make sense to me.

For giant jobs like this, the champ is Syncthing. The situation I describe above is my real-world use case. I like to manage my images on my relatively fast MacBook, but I sync copies to two ancient iMacs (running Linux) that I use as giant digital photo frames, while also maintaining multiple backups of my photos.

I also manage my ebook collection on my Mac, while syncing it to my self-hosted server so I can use Calibre Weband Audiobookshelf for remote access.

Scenario 5 -- I am traveling and need to get files onto the hard drive of my home computer so I can remote in and do X to those files.

If your cloud service of choice isn't an option--because it's acting flaky, you have space limitations, or for other reasons--using Blip is worth considering. Blip is a free service that can handle large, multi-GB files and resume transfers if they're interrupted. It uses TLS 1.3 for in-transit security.

It's not pure peer-to-peer; your data uses Blip's infrastructure for signaling. I sometimes have problems getting my devices, all signed into the same account, to see each other. Unlike LocalSend, Blip works across the internet, and plenty of people use it without issues.

My other suggestion in this category is Taildrop, the file-sharing protocol between your personal computers on the same Tailscale network. It's as easy as using the share menu on your Mac or mobile device. It's relatively new and still in alpha, but it's free, and I've never had an issue with it.

Scenario 6 -- I need to share a large file with a random internet stranger I may never talk to again.

This is a case where using a shared link from a cloud service or Nextcloud is your best bet. There are also browser-based sharing services that might work. PairDrop works well as a PWA in Safari.

Scenario 7 -- I have a collection of files I want to share with the internet at large and be able to update and change them.

There's no need to buy a domain name or open an account with a hosting service and CDN. Just use GitHub.

I'm no coder, but I've had a GitHub account for ages for several different reasons. It's what I use to share my automation settings for Keyboard Maestro, Hazel, and Better Touch Tool. Using GitHub Desktop, I can move files into a folder on my Mac and sync them to GitHub in just a couple of minutes.

You don't have to understand pull, push, or git to make use of GitHub. Once you have an account, you can also use it as a free backup service for Obsidian or even blogging platforms like Micro.blog.

A Couple of Newcomers

If you're interested in these kinds of apps, there are a couple of new ones worth keeping an eye on.

Zynk -- a new freemium service worth testing.

• Send folders, photos, and multi-gig archives
• Works across phones, laptops, TVs, and servers
• End-to-end encrypted
• Resumable transfers
• No size limits
• Built-in chat and voice
• Share via the app or browser links
• Preview files in the app before downloading

Droplet -- still in TestFlight. I'll be writing more about this when it's released. Droplet is an app for almost instantly moving files between Macs and iOS devices. It offers a simple drag-and-drop interface that literally takes about 15 seconds to learn.

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Someone asked me to name the best free app available to Mac users in 2026. I didn’t hesitate before choosing Tailscale.

Tailscale is a VPN, but not in the usual sense. It’s a private, encrypted, identity-based network where your devices recognize each other no matter where they are. It uses WireGuard technology and is often described as a mesh network. The terminology isn’t important. This isn’t the kind of VPN that simply masks your home IP address or anonymizes web traffic.

Tailscale lets you treat a collection of devices in different geographic locations as if they were all in the same building, plugged into the same network and connected to the same switch. In practice, you can link computers in your home, at your office, while staying in a hotel, and even machines belonging to family members. It works across platforms, and all traffic is end-to-end encrypted. You don’t mess with opening ports or exposing your home network to the internet. You don’t have to learn AWS, firewalls, or how to configure TLS certificates. The computers associated with your free Tailscale account are referred to as your Tailnet.

You don’t have to feel like you’re studying for your CCNA whenever you use software that relies on networking. If some of the details sound confusing, that’s fine. Tailscale doesn’t require you to understand subnets, routing, or DNS to be useful. You install it, sign in, and your devices can see each other.

If that sounds confusing, don’t worry. You don’t need to fully understand it to take advantage of the power of this free tool. You just need to learn how to use the Tailscale app, which isn’t overwhelming at all. You don’t have to understand subnets or routing.

One of the most useful features of Tailscale is the concept of an exit node. An exit node is a computer you control that has internet access. When you need to access the internet in a private and protected way from another computer, you can toggle a single switch in Tailscale to route your network traffic through that remote machine, no matter where you are.

I recently vacationed in Central America and relied on hotel Wi-Fi. I didn’t need to enable—or even install—a conventional VPN on my laptop. I simply chose a computer in my home, 2,000 miles away, as my exit node and used it as my gateway to the internet.

If you have a VPN subscription to a service like Nord or Mullvad that’s limited to a small number of devices, you can sometimes work around that limitation by using one of your machines as an exit node. You can even access that exit node from your phone, whether you’re on a cellular network or Wi-Fi. Once connected, all of your traffic appears to the receiving services as if it’s coming from your home computer.

I use a private tracker to download what are commonly referred to as Linux ISOs. That tracker only works when it sees my computer as being connected from the IP address assigned to my home router. If I’m traveling and need access, I just connect through the Tailscale exit node on my self-hosted server and everything works as expected.

There’s also an Apple TV app for Tailscale. I gave my brother, who lives on the opposite side of the country, access to my Tailnet so he can watch regional sports like NCAA basketball that are only broadcast locally.

Tailscale isn’t a replacement for every kind of VPN. It won’t automatically anonymize all your traffic the way a commercial VPN service does, and it doesn’t make unsafe devices magically secure. You still need good passwords, disk encryption, and basic common sense.

What it does exceptionally well is remove friction. It gives your devices a private, encrypted way to find each other without turning you into an amateur network engineer.

Using an iPhone or iPad with an SSH client, I can connect to my home-based Macs and Linux boxes to run scripts, reboot machines, restart services, and transfer files.

Because I can use macOS Screen Sharing, I can also easily access Macs belonging to family members for whom I provide technical support. When I need to remote into their machines, there’s nothing to set up. They don’t have to find or report their IP address to me. I can see everything I need in the Tailscale app.

Another use case for power users is remote backups using rsync. This is especially useful if you follow the 3-2-1 backup model: three copies of your data, on at least two different types of media, in at least two different geographic locations. You can set up a headless Mac or Linux box at a friend’s or relative’s house and sync your important documents and media with a simple script. As far as your computer is concerned, that remote system might as well be sitting right beside it.

A free Tailscale account allows you to add up to 100 devices and assign management access to three users. If you’re setting up computers for family members or friends who aren’t technically proficient, you don’t have to give up one of those seats. You install Tailscale using your account, and they rarely—if ever—have to do anything other than turn their computer on. From there, you can use tools like Keyboard Maestro, Hazel, and other automation utilities to get real work done.

Tailscale is good, solid technology packaged in easy-to-use apps. It still requires sensible password management, like any other tool. You’ll still want a conventional VPN if you need to anonymize traffic from at least one device. But Tailscale removes barriers that once made these kinds of setups the exclusive domain of network engineers—and it does so quietly, reliably, and for free.

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I've tried a variety of notch apps, and I haven't been truly happy with any of them. I'm not sure whether the novelty of the interface is the problem, or if it's the design of the apps I've used that bothers me. I recently installed Droppy, a free and open-source app built entirely with Swift for speed and stability, and I like it more than the other notch apps I've used.

It isn't overloaded with superfluous features, and the features it does have can be toggled on and off easily. It also seems very stable--I haven't encountered any bugs so far.

Utility Replacements

Depending on which features you enable, Droppy can replace several categories of single-purpose apps:

• Clipboard Manager -- Toggled off by default, you can enable a clipboard manager that's accessible from the notch interface. If you cut and paste a wide variety of elements all day long, you'll want something more powerful, but for casual use it gets the job done. It has keyboard controls, lets you choose how many items to keep in your history, and includes privacy protections like disabling password storage or excluding entire apps. If you copy an image containing text--whether it's a photo or a screenshot--Droppy can use OCR to extract that text.
• Mini Music Player -- The mini music player displays the current track and album art in the notch, with the usual controls for previous and next tracks, play, and pause.
• File Shelf -- Droppy lets you drag files in and out of the notch or into a floating window, much like apps such as Dropover, Yoink, and Gladys.

Extensions

Droppy's architecture allows you to add or remove features through extensions. This keeps the bloat down. You won't be faced with menu options for Spotify or Alfred if, like me, you don't use either of those products. The currently available extensions include:

• AI background removal
• Alfred integration
• Adding the Services menu
• Spotify integration
• Screen capture of UI elements
• Window snapping
• Voice transcription

Other Features

• A heads-up display appears when you use the keyboard controls for brightness and volume. You can also enable an HUD for AirPods if you use them with your Mac.
• On my M2 MacBook Air, Droppy uses about as much memory as Apple Notes or Messages--that is to say, not much. It does consume some CPU cycles and power, but it's not going to hog your system resources.
• You can choose to have Droppy appear as a notch even on Macs that don't actually have one. Alternatively, you can have it appear as a Dynamic Island to mimic the behavior on the iPhone. The functionality is the same either way.

Other Notch Apps

I tried Notchnook shortly after it came out, and it felt more like a minimally viable product than a finished app--despite its $25 price tag. It left a bad taste in my mouth.

Review of Notchnook

My second choice in this category is Dynamic Lake Pro, which sells for $15.90 on Gumroad. It has a couple of features Droppy doesn't, such as a weather and calendar HUD and notification support. It's updated frequently, and the developer is very responsive to bug reports and user questions.

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Apps gain new capabilities through updates. Our preferences change, task requirements shift, and workflows evolve right along with them. It pays to periodically reevaluate the tools and methods we rely on. As a writer and blogger, I go through a surprising number of images every day. My goal is simple: images should be optimized for file size, renamed intelligently, and land exactly where I need them for current projects. After 24 hours, they should be archived--still accessible, but no longer cluttering my active workspace.

Start with Downloads

Clotski is a menu bar utility for browsing, tagging, renaming, and editing metadata for images in user-specified folders--most often Downloads, Screenshots, and project folders. Its superpower is the ability to automatically save images from your clipboard to a location you define in the app's settings. In my setup, copied images are saved as JPGs directly into the Downloads folder.

NameQuick Steps In

NameQuick is a powerful automation tool that has improved significantly since I first started using it. Beyond AI-assisted renaming, it can move, tag, add comments to, archive, or trash images based on rules you define.

In my setup, NameQuick evaluates images in Downloads. Screenshots are renamed based on their content and the app that created them, with "Screenshot" appended to the filename. Once renamed, the files are moved into the folder where my current project files live. I use CleanShot X for screenshots for many reasons, but especially for how well it integrates with Raycast, ExtraBar, and CirMenu.

Other images follow a similar path: they're given short, descriptive filenames and moved into the same project folder.

Optimization

There's no reason to work with image files that take up more disk space than necessary. For that reason, I use Clop to automatically optimize every image I work with, unless there's a rare and specific reason not to. Clop watches the project folder and, when a new image appears, runs a process to reduce its file size. Its interface also makes it easy to upload files to cloud services, send images to an editor, compare diffs against existing images, and handle a handful of other related tasks.

Cleanup with Hazel

Most images in this setup exist for an immediate purpose: a blog post or a document I'm actively working on. By the next day, I usually don't need them anymore. To handle that, I use a Hazel rule that moves any file older than 24 hours into an archive folder. From there, another Hazel rule permanently deletes those files after 90 days.

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You don't need wads of disposable income to enjoy new software on a regular basis, and you don't have to rely exclusively on freeware to get useful work done on your Mac. You're the only one who knows what your budget can support. I've been buying independently developed software since before people called them apps--back when you dialed into a local BBS to download shareware from the computer eccentric you met at the last user group meeting. My hometown even had a store in the '90s where you could rent commercial software. This was before Little Snitch mattered, because most home users didn't even have Internet access.

Saving Money Without Being Miserable

1. Look for alternatives before you buy.
   Use AlternativeTo, a site that suggests apps similar to the one you're researching. The listings are rated and reviewed by regular people and clearly labeled as free or paid, open source or proprietary, with links to download or purchase.

   Here’s an example using Hazel as the starting point–I got 19 alternative suggestions in seconds.

2. Cancel free trials immediately.
   When you download an app with a free trial from the App Store, cancel the subscription right away. In 99% of cases, you'll still get the full trial period without the risk of forgetting and getting billed. You'll also get a reminder when the trial is ending, giving you time to decide whether the app is worth keeping.

   If you do subscribe, yearly plans are almost always cheaper than monthly ones. Be especially wary of weekly pricing. I recently tried a translation app that cost 49 cents for seven days–after that, it jumped to $10.99 per week.

3. Use software deal sites you trust.
   Bookmark a few reliable discount sites and check them regularly. The folks at Bundlehunt are building their own app store (currently in beta) with discounted apps like MacPilot, Menubar X Pro, KeyKeeper, Workspaces 2, and Alarm Clock Pro.
   Another solid option is Apps.Deals, where top-shelf apps like Spencer, TextSniper, and ProcessSpy are frequently discounted. All are on sale now.
4. Buy in November if you can wait.
   November is the best month of the year to buy software. In the indie world, offering Black Friday savings has become a tradition with deep discounts. Reddit, GitHub, and tech bloggers usually maintain running lists of deals. With a little patience and research, 40--50% discounts on premium software are common.
5. Use AppRaven to track prices and freebies.
   Appraven is an iOS app that connects you to a community of people who genuinely love software. It tracks current and historical App Store prices across Apple platforms, which makes it easy to tell whether a "sale" is real.
   You can get near-instant notifications when paid apps temporarily go free, browse curated user-created lists, and create wish lists that notify you when prices drop. One of my favorite lists to follow is focused on apps that support Apple Shortcuts.
6. Use educational discounts if you're eligible.
   If you have an email address tied to a K--12 or higher-ed institution, there are a lot of legitimate discounts available. There's even an education-only app store called Student App Centre. Apple also offers education pricing on hardware.
7. Stick to curated sources for free software.
   Curated lists reduce the risk of downloading an unvetted GitHub project that turns out to be malware. A few good starting points:
   • MacUpdate Search -- recent releases of free Mac apps
   • OSS Software -- more technical, but approachable
   • thriftmac -- 400+ quality free Mac apps
   • Mr. Free Tools -- software and web services
   • MacMenuBar -- Recently Added -- one of the best Mac software sites around
   • Today on Mac -- thoughtful reviews
   • Top Mac Apps -- from the MacUpdater app
   • Privacy Tools -- excellent for security and privacy
   • Awesome Free Apps on GitHub -- a long list worth exploring carefully

Saving Money the Dumb Way

Don't download cracked or pirated software. It's easy to find sites with massive catalogs of apps, usually delivered at glacial speeds unless you pay for "premium" access (Bitcoin preferred). Even when the apps are recognizable titles, they're often modified in ways that break Gatekeeper, Apple's built-in malware protection.

To compensate, these sites usually provide a mysterious Terminal script you're told to run. None of this is smart. Even if nothing immediately bad happens, you're often left with an app you can't update without breaking it.I don't lose sleep over Adobe's or Microsoft's profits, but stealing a $4.99 app from an independent developer who built something genuinely useful is just low-class.

I also have mixed feelings about asking developers for freebies or discounts. Some--like Sindre Sorhus--openly encourage students and users in low-income countries to reach out, which makes sense. I'm privileged enough not to need that. On the flip side, I regularly get emails from people who assume I'm the developer of an app I reviewed. Most are polite; some are pushy. Decide where you land, and act accordingly.

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Complex, multi-purpose apps with a zillion functions can be fun to learn, even if you never quite feel like you've mastered them. Every time I tinker with my Raycast setup or my collection of Keyboard Maestro macros, I get the nagging feeling that I'm not making the best use of those apps. To remedy that feeling, it's refreshing to discover a few simple apps that do one thing well--and that's all. Here are a few I've been tinkering with lately.

• Clean Links (Free) -- Although there's a useful Raycast extension to strip tracking info from links on your clipboard, Clean Links--a universal app that also works on iPhones and iPads--offers a bit more functionality. It can show you the URL embedded in any QR code, and it can also generate QR codes you can share or print. It works with Apple Shortcuts for anyone who enjoys a little automation, and it has a robust privacy policy: no ads, no trackers, no telemetry.
• Photo Sort ($4.99) -- Try this: open Apple Photos on your Mac. Select an album--or your entire library--and try to sort by file size. I'll wait… As you've probably discovered, that's not a feature Apple offers, for some strange reason. I had some huge (100MB+) TIFF files and a lot of RAW images in my library, and while finding them was possible, it wasn't simple. With Photo Sort, it's as easy as clicking a button to identify the biggest files and start saving iCloud storage. Photo Sort can also identify high-quality images, helping you spot the keepers (in focus, properly exposed, good white balance) and ditch the blurry, dark, out-of-focus junk.
• Russet (Free) -- If you want to use agentic AI tools for your calendar and contacts, or extract data from PDFs without having to search manually, check out Russet. It's a well-designed front end for Apple Intelligence (Apple Silicon only) that requires no API keys and no accounts with third-party AI companies. Russet also has a few whimsical touches that are fun to explore in your downtime, including a feature that collaborates with you to create text-based adventures and immersive stories. You can also take advantage of Apple Intelligence writing tools for proofreading and revision, with an additional option to use a biometric lock to keep your work private. Everything Russet does stays on your device. It doesn't require an internet connection.
• Float Tube ($2.99) -- If you use Safari with YouTube, you can't natively scroll through comments and watch the video at the same time. Scroll down, and the video disappears. With Float Tube, a Safari extension, a floating picture-in-picture window appears as you scroll, allowing you to keep watching while reading comments and notes. Float Tube will also display the video's subtitles.
• Floxtop ($19.99) -- For years, I've used the same organizing structure for my ~/Documents folder. I created a Hazel rule that sorts files by extension, and while I've made it work, I'd never claim it's the most efficient approach. When I'm looking for an image, I don't always know whether it's a JPG or a JPEG. If someone sends me a Word document, I'd better hope I gave it a descriptive name, because otherwise I'm scanning files until something looks familiar. Floxtop offers a better solution. It uses on-device AI to analyze files and group them into related subfolders. I had dozens of PDF receipts, and it sorted them instantly--without my having to create manual rules like I would with Hazel. It recognizes text and images, and it gives you a chance to review everything before applying changes. Sorting a folder with 100 documents goes from 100 tiny decisions to a single step. And I have to say, I really enjoyed interacting with the developer.

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Rather than trying to consolidate all the image tools I use into one giant app with hundreds of features, I prefer to use smaller, specialized apps that are single-purpose or that have a small feature set. They are easier to learn, faster to launch, and often maintained by a very experienced developer with years of experience. Here's a collection of such apps that you might find useful.

Toyviewer, My Default App for Opening & Viewing Images

Dating back to the 90s, Toyviewer (free) can open just about any image format you throw at it, including ones that Preview won't touch. You can view images one at a time or use its slide show mode. For simple, one-off edits, ToyViewer can adjust the brightness, contrast, and color tone of images, and perform enhancements, embossing, etc. It does file conversions, and you can also print from it.

ImageOptim, My Go-To for Shrinking File Sizes

ImageOptim (free), a powerful compression app, can be accessed by dropping images on its icon in the dock, through integration with macOS services, or by opening the GUI and dropping a single file or a batch of files into the interface. It is essentially a wrapper for a powerful set of compression tools. It's capable of reducing file sizes by up to 90% with no discernible quality loss. It does its work quickly, even on older Macs. If you are a Qspace user, you can add ImageOptim to the right-click menu. You can recover the original files without losing access to the converted ones.

XnConvert for Batch Image Operations

If you come across a folder of RAW photos, a collection of giant TIFF files, or maybe some PSD files that never got finished in Photoshop, you can use XnConvert (free) to turn them into something manageable and useful all at once. Not only can you batch convert them into a new format, but you can also do resizing, renaming, adjusting colors, applying filters and effects, and editing metadata all in one go.

Digikam for Management

I keep one canonical collection of photos for myself and my wife in the file system of my daily driver that gets synced to other computers, a couple of backup drives, and two cloud services. I still use iCloud for the photos I take with my phone, but just for the sake of convenience in viewing and sharing; I don't try to make it the comprehensive, go-to source for my entire photo library. Digikam (free) is a huge app with more features than Adobe Lightroom. I use it for facial recognition, tagging, filtering, and file management, but it can do a whole lot more. I installed the Linux version on two old 24-inch iMacs just to use them as extra-large digital photo frames.

Immich for Sharing and Remote Access

I use Immich (donationware) in a Docker container that reads the file structure I maintain in Digikam. Using the companion iOS app, I can remotely access my entire photo collection on my phone using its powerful search features, albums, and tags. I can also use its built-in web server with a domain I own to get to my photos from any Internet computer. The Immich developers give you access to the entire feature set right off the bat, but they do ask that you help support the app financially if you continue to use it.

Some Other Useful Tools

• Better Finder Attributes ($24.95) - I am relentless about the way I organize my photos. All my file names contain the date the photo was taken. I have digital photos dating back to 1995 that have lived on many, many computers, drives, and servers through the years. Periodically, the EXIF data gets corrupted or missing or overwritten, but I can always fix it with this app.
• Better Finder Renamer ($29.95) - This is the most powerful and fastest renaming utility in the Mac world. If you can come up with a renaming concept in your mind, the chances are that you can accomplish it with this app. Like I said, my naming system is at the heart of my whole management workflow. This makes it easy.
• Parachute Backup ($4.99) - If you stay in the Apple Photos world, but you want a good backup option, this is the one to use. Remember, iCloud is a syncing service, not a backup service.
• Syncthing (free) - If you manage your own photos in your file system like I do, this is the tool to use to sync them in real time to other computers (e.g., a self-hosted server) within your network.
• PhotoSweeper ($15) - The fastest and most full-featured duplicate manager for Macs.
• PowerPhotos ($39.95) - If you want to use Apple Photos but need features it doesn't provide, this is the tool to get to manage multiple iCloud libraries, to batch edit metadata, to search multiple libraries at once, and to copy and move files between libraries. If you don't use PhotoSweeper, the PowerPhotos duplicate finder is also pretty solid.
• Acorn ($19.95) - If you want to do real editing work on images but don't want to buy an 800-page book of instructions or get an Adobe subscription, the app I suggest is Acorn. A two-time Apple award winner, it's a one-time purchase and you get access to extensive online documentation, a user forum, and tech support. The current version is a universal binary compatible with macOS 14 and 15, but earlier versions can still be downloaded.

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ExtraBar is a new app from the developers at AppItStudio. That's the same team behind ExtraDock and DockFlow, two useful additions to my toolbox in 2025. ExtraBar is one of those apps that solves a problem I didn't realize I had. My Mac's menu bar is cluttered with icons from (don't hate) 40 different apps. Traditionally, the way to tame that was by using Bartender, Ice, or some other menu bar manager. Apple, in an attempt to Sherlock those apps, introduced a few menu bar management tools in macOS 26. In doing so, it changed the back end for utility developers, and it's been a scramble for months for a lot of folks to find something that works the way they want it to.

Enter ExtraBar. It doesn't try to mimic the old menu bar management paradigm. It provides users a way to perform a huge number of actions by allowing them to associate their favorite use cases with menu bar items that can be hidden until needed or left permanently on display. The entire interface is accessible through keyboard shortcuts. Everything I describe below can be done without using a mouse.

Keyboard Maestro In my first day of use, I was able to eliminate the native Keyboard Maestro menu item, which I use multiple times a day, by creating a custom Keyboard Maestro action list with ExtraBar.

Apple Shortcuts There are several apps and a native way to activate Apple Shortcuts from the menu bar, but now I can do that from ExtraBar. This means I can build my own launcher for individual apps. I can batch open groups of apps, documents, and websites easily too.

Messages and Mail I was able to quickly build a menu bar action list that opens Apple Messages to a specific contact, with the cursor in the message box ready for me to type. The same concept applies to my email client.

Raycast I have installed more Raycast extensions than I can keep up with, and I often get frustrated because I can't remember the correct alias or keyboard shortcut for the function I want. Those days are gone. Now I can make a menu to choose from, ordered in any way I want and containing up to 35 items. Some of the apps I was able to eliminate from my menu bar as a result include Drafts, Fantastical, CleanShot X, and Things 3.

One nice touch about the app is that you can export and import action lists. This has been a useful feature in other automation apps, like Hazel and BetterTouchTool, and I think it will be helpful here too.

There are still a lot of possibilities to explore. I can search Obsidian with an ExtraBar action. I can search my Raindrop bookmarks. I can start and record AI Q&A sessions. I've already submitted a feature request to the developers to allow users to create their own action lists (using shortcuts and deep links) that are associated with workflows and not with single apps. They have a history of responsiveness and frequent updates with their other products, and I expect we will see more of the same with ExtraBar.

Learn more about ExtraBar and by all means, buy a copy (€9.99) at the developer's website.

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Paid Mac Apps – Power User Index

If you got some cash or gift cards for Christmas and want to try out some new software, you can try a few of these apps. I've installed and tested them all at some point. The links will take you to a short review with download information. If you find a broken link or an app is no longer viable, let me know and I'll make a quick edit. If you're a developer, drop me a DM and I will be glad to check out your work and possibly feature you on AppAddict if it has some unique features the community would appreciate.

Note - In almost all cases, I've listed the purchase and/or subscription price at the time I reviewed the app. Some have undoubtably changed, so make sure you check the current price before purchasing. None of these are affiliate links, they lead to wherever the developer markets his app. This is my hobby, not my part time job.

🗂 File Management, Backup & Disk Utilities

• DaisyDisk — Visual disk usage analyzer for quickly reclaiming storage.
• SuperDuper — Reliable disk cloning and bootable backup utility.
• Backup Loupe — Inspects Time Machine backups for errors and missing files.
• Backup Status — Monitors Time Machine health and backup success.
• Parachute Backup — Backup solution designed specifically for iCloud and Photos.
• Path Finder — Finder replacement with advanced, multi-pane workflows.
• QSpace — Keyboard-driven, multi-pane file manager for power users.

📝 Writing, Notes & Knowledge Management

• Drafts — Automation-first text capture and processing environment.
• iA Writer — Minimalist writing environment focused on clarity and structure.
• EagleFiler — Long-standing personal information manager for local archives.
• Thoughts — Inspiration and idea manager for creative thinking.
• Quotemarks — Personal quote collection and reference notebook.
• Bebop — Lightweight quick-notes app for rapid capture.
• Scratchpad — Floating notes app designed for temporary thoughts and fragments.

⚙️ Automation, Launchers & Power Tools

• BetterTouchTool — Deep customization and automation for input devices.
• PopClip — Contextual text actions available anywhere on the system.
• Raycast — Keyboard-driven launcher and automation hub.
• Shortery — Automation bridge between macOS events and Shortcuts.

🎨 Media, Images, Audio & Video

• CleanShot X — Best-in-class screenshot and screen recording utility.
• Acorn — Affordable, capable image editor without subscriptions.
• Permute — Simple, powerful media converter for audio, video, and images.
• Downie — Video downloader with broad site support.
• SoundSource — Advanced per-app audio routing and control.
• Swinsian — Music player designed to avoid feature bloat.

🖥 Interface, Window & Workflow Enhancements

• Better Display — Advanced control over display scaling and external monitors.
• Witch — Multi-featured app and window switcher for keyboard users.
• Wins — Window snapping and management utility.

🔐 Security, Privacy & System Protection

• EtreCheckPro — Deep system diagnostics and troubleshooting reports for complex Mac issues.
• Sensei — System monitoring and maintenance tool aimed at advanced users.
• NextDNS — Network-level privacy, tracking, and malware protection with granular controls.
• CleanMyMac X — All-in-one cleanup and monitoring suite with notable trade-offs.

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