Once upon a time, computers couldn’t remember what documents/windows were open the last time you used a given application. Browser tabs were easily lost unless you had bookmarked them. And it was generally difficult to pick up where you left off after restarting your Mac.

In 2011, OS X Lion introduced the ability to remember what was last open and reopen it after login. You’ll find a system setting on the Mac where you can indicate your preference about reopening application windows that were open the last time you quit the app, whether manually or as part of logging out, restarting, or shutting down.

A similar setting is present in the Log Out, Restart and Shut Down dialogs. Additionally, you can override this setting on a per-app basis.

Shut Down Dialog

If you use a keyboard that has an Eject key (⏏), you can press Control+Eject. Or, you can hold Control and press the Mac’s power button (as long as this is separate from the Touch ID key on a MacBook’s built-in keyboard). Either of these shortcuts will pop up the Shut Down Dialog, offering commands to Restart, Sleep, or Shut Down the Mac.

From here you can press R for Restart, S for Sleep, Escape for Cancel, and Return for Shut Down. More related shortcuts in this support article.

Additionally, you’ll see a checkbox: Reopen windows when logging back in. You’ll also see this checkbox when you click the Restart or Shutdown command in the Apple menu. (In all of these cases, you must be the only user logged into the Mac.)

If you have Keyboard Navigation enabled, the checkbox will have focus initially and you can press the space bar to toggle it. If you uncheck the box, the next time you log into your Mac, the only applications that open will be the ones specified in Login Items in System Preferences/Settings.

System Preferences/Settings

In System Preferences > General and System Settings > Desktop & Dock, there’s a setting called Close windows when quitting an application. When enabled, any time you quit an application, your Mac will not remember the windows or documents that were open and so won’t show them the next time you open the app.

This is the global setting that sets a default for all applications. Apple also outlines some additional ways to prevent windows from reopening. Although the vocabulary differs slightly between applications and windows, there is greater sameness than you might think between this toggle and the ones detailed above.

Also, note that if an application is listed in the Login Items system setting, it will open at login, but if any other setting prevents windows from reopening, multi-window applications in Login Items will not show their prior windows on open. Instead, they will show any windows that open by default, generally as specified in the application’s settings.

Application Menu on Quit

When the above system setting is disabled, the Mac will remember and reopen any windows of an application that were open when it was quit. When it is enabled, the Mac close those windows as part of the quit process, thus forgetting them before you open the app anew.

To override either of these experiences, hold Option when quitting the application. If you look at the Quit command in a multi-window application’s menu, you’ll see it change when holding Option. When the global setting is disabled, the command becomes Quit and Close All Windows; when it’s enabled, the command is Quit and Keep Windows.

What’s all this about “multi-window applications”? Some Mac apps operate in just a single window, such as Photos and System Settings, whereas others allow multiple windows or lack awareness of this reality. Thus, this command override is not available in single window applications.

When you restart your Mac, do you benefit from the ability to pick up where you left off? Do you want to avoid losing website tabs if you have to update your browser? How else do these settings help you experience productivity and/or flexibility with your technology?