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What is Stairways Software?

Stairways Software is a long-running Macintosh-only software company, best known for Keyboard Maestro, a macOS automation and macro tool. The company positions itself around keyboard customization and productivity: you build macros that trigger from keystrokes, menus, or other events, then let them handle repetitive tasks on your Mac.

Its main audience is Mac users who want to automate routine actions rather than write full programs. Typical uses shown on the site include typing a saved email address, opening a website or app, and duplicating a line of text. The pitch is broad: if you can do something manually, Keyboard Maestro can likely automate it.

A few practical trade-offs to know:

• Mac-only. This is not cross-platform automation software, so it won't help on Windows or Linux.
• Power vs. setup time. Simple macros are quick to create, but more elaborate automations take planning and testing.
• Permissions matter. macOS accessibility and location permissions can interfere with keystroke, menu, and location-based actions, and the site notes that these sometimes need toggling off and on.

As a next step, decide what you'd automate first — something small like expanding a signature or launching a daily set of apps — then check whether Keyboard Maestro's trigger-and-action model fits that task. For comparison, Mac automation users also often look at Apple Shortcuts and Folivora BetterTouchTool, though Keyboard Maestro is the more macro-centric option.

What can Keyboard Maestro automate on a Mac?

Keyboard Maestro is a macOS macro program from Stairways Software. Its own description is broad: if you can do something manually on your Mac, it can almost certainly be automated. That covers both tiny personal shortcuts and multi-step workflows.

H3 What it can automate, in practice

• Typing and text expansion — inserting your email address, common replies, snippets or signatures.
• Launching and switching — opening apps such as Pages, jumping to Gmail or Facebook, or moving between windows.
• Editing chores — duplicating a line, copying and pasting, selecting menus by name.
• Menu and interface control — choosing menu items by name, which lets a macro drive apps that lack scripting support.
• System and context actions — creating calendar events, sending Pushover notifications, using Apple text recognition, and getting your location (the location action needs Location Permission).
• Chained workflows — combining triggers, keystrokes, app launches and actions into one command you invoke with a hotkey, typed string or other trigger.

H3 Who gets the most out of it

H3 A concrete scenario

Say you handle customer replies. One macro could open your mail app, paste a standard greeting, insert the customer's name, attach a template and log a calendar reminder. Instead of five manual steps, it becomes one keystroke. The same logic applies to weekly reports, file renaming or preparing meeting notes.

H3 Before you start

Expect permission friction. Stairways notes that macOS Accessibility permissions can misbehave: if keystrokes, menu selection or copy/paste stop working, toggle Keyboard Maestro and Keyboard Maestro Engine off and on in System Settings → Privacy & Security → Accessibility, or remove and re-add them. Budget a few minutes for this when you first install.

H3 Next step

Pick one task you repeat daily, time it, then build a single macro for it and assign a hotkey. If you want to compare approaches, Keyboard Maestro's own material is at Stairways Software, and you can see how Apple's built-in automation compares at Apple Support or explore the scripting route at Apple. For a free, code-based alternative on macOS, GitHub hosts many open-source automation projects worth reviewing.

How much does Keyboard Maestro cost and how do I upgrade?

Keyboard Maestro is sold by Stairways Software as a one-time purchase: the listed price is US$36 for a new license, and an upgrade is US$25. Both figures come from the product page, so treat them as the vendor's current listed pricing rather than a subscription rate.

Stairways Software

How upgrading works in practice

• The upgrade price applies to existing licensed users, not to first-time buyers. If you already own a license, you pay the lower upgrade amount instead of the full price.
• The site provides a "What's My License?" lookup and a user database area where you can check the license tied to your email address before buying. Do that first, because it tells you whether the system sees you as a new customer or an upgrade customer.
• Keep the email address you originally used. If you have changed addresses, the lookup may not find your record, and you would need to contact Stairways to sort it out before paying.
• After purchase, keep your license details somewhere you can find them, since future upgrades and re-installs will depend on matching that record.

A concrete scenario

Suppose you bought a license a few years ago on your work email and have since moved to a new job. Before clicking upgrade, run the license lookup with the old address. If it returns your license, upgrade at US$25 and then update the registered email. If it returns nothing, resolve that with support first; otherwise you risk paying the full US$36 for something you already own a path to.

Decision criterion

Buy new at US$36 only if you have never held a Keyboard Maestro license. If you have any prior license, verify it and take the US$25 upgrade. The gap between the two is small enough that the real cost is the time spent confirming your record, not the difference in price.

Next step: open the product page, run the license lookup, and only then choose between the buy and upgrade options.

How do I fix Accessibility permission problems in Keyboard Maestro?

Toggle the permissions off and back on — that's the fix Stairways Software itself describes. In the page's own words, if typing keystrokes, selecting menus, copy/paste or similar actions fail, you go to System Preferences → Security & Privacy → Privacy → Accessibility and switch Keyboard Maestro and Keyboard Maestro Engine off, then on again. If that doesn't take, remove both entries and let macOS re-add them (usually by launching the app and accepting the prompt).

Why it breaks in the first place

Stairways notes that every macOS release since Mojave has had some form of Accessibility permission problem. The permission is stored against the app's identity, so an update, a move to a new Mac, or a restored backup can leave macOS believing the app is a different program than the one you approved. The checkbox still looks ticked, but the grant no longer applies.

A reliable order of operations

1. Quit Keyboard Maestro and Keyboard Maestro Engine (both, not just the editor).
2. Open System Settings/Preferences → Privacy & Security → Accessibility.
3. Remove Keyboard Maestro and Keyboard Maestro Engine with the minus button, or toggle each off.
4. Relaunch Keyboard Maestro and accept the permission request when it appears.
5. If nothing appears, toggle the entries back on manually.
6. Reboot if the checkbox state and the actual behaviour still disagree.

What this looks like in practice

A typical case: you upgrade macOS overnight, and the next morning your "type my email address" macro pastes nothing, while a macro that only opens an app still works. That split — actions that simulate input fail, actions that just launch things succeed — is the signature of a lost Accessibility grant rather than a broken macro. Rebuilding the macro is wasted effort; re-granting the permission is the actual fix.

One related note from the same page: wireless/location-based macros need Location Permission, which macOS may never request on its own. Stairways points to the Get Location action in version 11.x to force the prompt.

Preventing repeats

• Re-check Accessibility after every macOS upgrade and after migrating to a new Mac.
• Keep the app in a stable location rather than moving it between folders.
• If you use a sync or backup tool, expect to re-grant after a restore.

For version-specific behaviour and current requirements, the vendor's own documentation is the authority: Stairways Software. If you'd rather avoid permission-sensitive automation entirely, macOS Shortcuts and AppleScript's built-in menu commands cover some of the same ground with fewer grants, though with far less flexibility.

Which macOS versions are compatible with Keyboard Maestro?

Keyboard Maestro works across a very wide range of macOS releases. According to Stairways Software, all versions of Keyboard Maestro back to 4.3.2 run on the current macOS release (referred to on the page as “Golden Gate”), and the same statement is made for every macOS version since Mojave.

That backward compatibility is unusual for Mac automation tools, which often drop older systems quickly. In practice it means:

• Old Macs kept on older systems: If you are running Mojave or later but cannot update further, a current Keyboard Maestro license still covers you.
• New Macs on the latest macOS: The newest release, Keyboard Maestro 11, is the version to use, and it is the one that receives new features such as the Macro Wizard, a Security preference pane, Apple Text Recognition support, and actions like Prompt For Snippet, Create Calendar Event and Send Pushover Notification.
• Mixed fleets: If you manage several Macs on different macOS versions, one product version can serve all of them, which simplifies licensing and macro sharing.

Two practical caveats come from the developer’s own notes. macOS since Mojave has had recurring Accessibility permission problems, which affect actions that type keystrokes, choose menus or use copy/paste. The fix is to toggle Keyboard Maestro and the Keyboard Maestro Engine off and on again in System Settings → Privacy & Security → Accessibility, or remove and re-add them. Separately, wireless location information needs Location Permission, which the system may not prompt for; the Get Location action in version 11.x can force that request.

If you are unsure whether your exact macOS build is covered, the sensible next step is to download the current version and test a simple macro — such as inserting your email address or opening a frequently used app — on your own machine before buying.

How do I find or manage my Keyboard Maestro license?

License management for Keyboard Maestro lives on Stairways Software's own site, not inside the app. The page offers a "What's My License?" lookup and a user database for managing the email address tied to your purchase, alongside the option to receive announcements.

Stairways Software

Practical steps for a typical owner

• Open the "What's My License?" page and enter the email address you used at purchase. If you've changed addresses since then, the user database is where you update it so future lookups and upgrade notices reach you.
• If you're reinstalling or moving to a new Mac, retrieve the license first, then enter it in Keyboard Maestro's registration window rather than hunting through old email receipts.
• Upgrading from an older version is a separate path from a fresh purchase, so check which one applies before paying. The page lists a full price for Keyboard Maestro and a lower upgrade price, but confirm current figures on the site itself, since they can change.

Whose experience this reflects

The page's own notes describe two recurring friction points rather than license issues: Accessibility permissions on recent macOS versions, where you may need to toggle Keyboard Maestro and Keyboard Maestro Engine off and on in System Settings, and Wireless location data, which may require Location permission or the Get Location action in version 11.x. Those are the developer's observations, not mine. My read: if automation suddenly stops typing keystrokes or selecting menus after a system update, check permissions before assuming a licensing problem — the two look similar because the app appears inert either way.

A quick decision rule

If the lookup returns nothing, try alternate addresses you may have used, since the record is keyed to the purchase email.