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A frustrating experience with Apple Smart Keyboard and iOS Third Party Keyboard

I recently started using a service called Grammarly on my Mac. The software does proofreading via a browser extension and a desktop text editing app. It’s great for people who create a lot of documents (security architects) but is useful in general.

Because of iOS sandboxing the only way Grammarly works on my iPad Pro is via their third-party iOS keyboard. However, I was disappointed to learn that when an Apple Smart Keyboard is attached, iOS disables all third-party keyboard apps. I can only use Grammarly when typing directly on the iPad Pro display. But my typing speed is significantly reduced compared to a physical keyboard like the Apple Smart Keyboard. Argh!

I also discovered that there is a bug in the Apple Smart Keyboard. Sometimes when the arrow navigation keys are used, iOS deletes all content in the edit screen. Shaking the iPad Pro does not always prompt iOS to activate the “Undo” feature.

The ESC key, iOS and the Apple Smart Keybaord

I have remote Linux servers that I want to manage. There are many apps in the App Store for doing this. I am using one of the top apps, Prompt. Prompt is a full functional terminal app supporting username/password logins as well as SSH key logins.

PasswordAuthentication no

PubkeyAuthentication yes

ChallengeResponseAuthentication no

I configured SSH on my Linux servers to disable password login for root and allow public key authentication only. I can access the Linux console from the Digital Ocean web front end (two-factor auth). I generate a public SSH key in Prompt and copy to clipboard.

I need to add the public SSH key for the iPad Pro to the .ssh/authorized_keys file. I access my Linux console in the DO web front end and open the authorize_keys files in Vim. I paste in the public key but ... neither the Apple Smart Keyboard, nor the default iOS keyboard have an escape key.

Prompt (and the many other terminal apps in the App Store) provide a virtual ESC key but I can’t use Prompt to access my servers until I add the iPad Pro SSH key to the server.


It seems the only thing I can do is to enable password logins, login with Prompt, add the SSH key, then disable password logins.

I visited the Apple Support forums and poked around the web ... but I found more questions than answers.

The iPad Pro is marketed as being the iPad for professionals but I think this mostly applies to non-technical professionals.

  • Prompt 2.67

  • iOS 12.01

  • 10.5" iPad Pro