After weeks of setting up Mac automation and workflows, there are still some fundamental limitations that just can’t be automated away. Here are the friction points that remain.
Cloudflare Captcha vs VPN: The Irony
Cloudflare captcha no longer works with VPN—confirmed. I can’t log into Cloudflare anymore (the irony) because their captcha system blocks my GCE-based WireGuard VPN.
This is particularly frustrating because Cloudflare is supposed to be developer-friendly, yet their own security measures prevent you from managing your Cloudflare services when using privacy tools they should understand.
Monitor Sleep Automation Failure
I have so many apps keeping my Mac awake that my monitors won’t go to sleep automatically. The problem is I haven’t found a way to automate this properly.
What I want: When I walk away from my Mac (detected by Apple Watch proximity), automatically turn off all monitors.
What I have: A hard-coded AppleScript that I assigned to my Stream Deck. When I press the button, all my monitors go to sleep.
This manual approach works, but it’s not the seamless automation I was hoping for. The Apple Watch proximity detection for screen sleep just doesn’t seem to exist or work reliably.
iPhone Mirroring: Too Small for 4K
iPhone mirroring is great in concept, but I’m on a full 4K display and I can’t resize the mirrored phone screen. It’s so small that it’s almost unusable.
I just wish I could expand the size and zoom in. The feature works perfectly for functionality, but the fixed size makes it impractical for actual use on high-resolution displays.
Amphetamine: A Non-Solution
I tried Amphetamine to manage sleep settings, but it doesn’t solve the core problem. With so many development tools and background processes keeping the system awake, adding another sleep-prevention app just makes the monitor sleep issue worse.
What Works vs What Doesn’t
Automation that works:
- Stream Deck scripts for specific actions
- Keyboard shortcuts for date entry (via Keysmith)
- App-specific automation within individual tools
Automation that doesn’t:
- Proximity-based screen management
- Intelligent sleep detection with multiple apps running
- VPN compatibility with security-heavy services
The Apple Watch Integration Gap
Apple Watch integration works great for unlocking the Mac, but it stops there. The proximity detection for automated actions seems limited or unreliable.
I expected more seamless “when I leave, do this” automation, but the reality is much more manual than Apple’s marketing suggests.
Living with Limitations
These aren’t deal-breakers, but they highlight that even in Apple’s tightly controlled ecosystem, there are workflow gaps that can’t be automated away.
The solution has been creating manual triggers (Stream Deck buttons, keyboard shortcuts) for actions that should be automatic. It works, but it’s not the seamless experience I was hoping for.
Some of these might be solvable with more complex scripting or third-party tools, but the fact that basic proximity automation isn’t built-in shows the limitations of even the most integrated ecosystem.