Cannot close apps by right-clicking Dock icons on MacBook Pro

You should be able to secondary-click (control-click, right click) on an app in the Dock and select Quit, that is a standard and expected behavior in macOS, and it's what I see in macOS 27.2.

What options do you see when you secondary-click on a Dock icon?

Note that there are several ways to quit an app on macOS.

Quit apps on Mac - Apple Support

Have you rebooted your Mac? If not, that's the first step. If that does not help, then see if the problem is present when you boot in safe mode. That process performs some system cleanup and clears caches, and also disables 3rd party extensions that may cause problems.

Start up your Mac in safe mode - Apple Support

If that does not correct the issue, test in a new user account. A newly-created user account will have all settings at default, and if the issue does not occur in that new account then it provides guidance on what may need to be changed to correct the issue.

Add a user or group on Mac - Apple Support

Once the testing is complete, the new account can easily be deleted.

Delete a user or group on Mac – Apple Support

Those steps will help to isolate the problem.

It might help to download and run EtreCheck, written by a long-time forum member. The free version is fine. Post the full report using the Additional Text button. No personal information is revealed. 

What you describe sounds more like a temporary problem with macOS handling Dock clicks or delivering the Quit command, rather than an app that refuses to close.

The most useful clue is that clicking Quit two or three times eventually works, and after the Mac has been running for a while, it starts working on the first click. That suggests something may be temporarily busy, delayed, or behaving inconsistently during startup.

What conditions could cause this?

Here are the main possibilities, in roughly the order I would investigate them.

1. Dock or Finder temporarily busy. The Dock is responsible for displaying the contextual menu and initiating the Quit action. If the Dock process is busy or momentarily unresponsive, a click might appear to do nothing. Restarting the Dock can sometimes resolve this kind of behavior.

2. Background startup activity. After login, macOS may be loading login items, syncing files, indexing Spotlight, restoring windows, or starting background services. Heavy activity could make the interface sluggish for a while. However, that would be a possible explanation, not proof of the cause.

3. An app is slow to respond to Quit. Some apps have to finish saving data, process a dialog, or respond to a request to terminate. This is more likely if the problem affects only one or two particular apps rather than every running app.

4. A background utility or login item is interfering. Window managers, clipboard tools, mouse utilities, menu-bar apps, and other third-party software can sometimes affect normal macOS interaction.

5. A macOS bug or corrupted Dock preference/state. If the issue affects many unrelated apps and persists after startup activity has settled, a software bug or a problem with the Dock's state becomes more plausible.

The fact that you can quit apps from the menu bar is especially useful: it suggests that the applications themselves can still receive and act on a Quit command. It doesn't completely rule out an application-specific problem, but it makes a general failure of the apps less likely.

How I would narrow it down

Since you're already considering Safe Mode, that's an excellent next step.

1. Test in Safe Mode

Use the Mac in Safe Mode and test whether Dock → Quit works immediately after startup and again after a few minutes. If the problem disappears, that points toward startup software, extensions, or caches, although it doesn't prove which one is responsible.

2. Restart the Dock process

Open Terminal and run:killall Dock

The Dock should disappear briefly and relaunch automatically. This doesn't normally remove your Dock settings. If that fixes the problem immediately, it supports a Dock-related issue, though it doesn't establish the underlying cause.

3. Check Activity Monitor when it happens

Open Activity Monitor and look for unusually high CPU usage or processes marked “Not Responding.” If the issue occurs mainly just after login, compare what is happening then with what you see once the Mac settles down. Apple documents how to inspect and quit unresponsive processes in its Activity Monitor guide.

One important distinction

Apple's documentation confirms that Control-clicking (the equivalent of right-clicking) an app in the Dock and choosing Quit is the normal way to close an app. 

There is also a distinction between an app that ignores a Quit command and a Dock that fails to deliver it. Your observation that repeated clicks eventually work makes the second possibility worth investigating first.

My main question is: when this happens, does clicking Quit fail for every running app, or only certain apps? And does the Dock still respond normally when you right-click an icon and select other options?

Those two details would help distinguish a Dock-level problem from an app-specific or background-process issue.

This may depend on whether the app is actually running.

To test this properly, the app must be open or running in the background. 

Simply seeing its icon in the Dock does not mean it is running, as the Dock can also display recently used apps.

Open Safari (or another app) and check that the small dot appears beneath its Dock icon. 

According to Apple, this dot indicates that the app is open.

When an app is running, right-clicking or Control-clicking its Dock icon should display a shortcut menu with Quit available. If the app has already quit, that option may not appear.

Try this test to determine whether the problem is related to the app's running state or a possible macOS 27.2 bug.

Apple Support references:

Get to know your desktop, menu bar, and Dock

Quit apps on Mac

If an app continues running in the background after you quit it

Mail is open and running in the background although it is minimize

Contacts is Totally Closed and Not Minimize and running in the background

EtreCheck may reveal some actionable information, but then again it may not. Either way posting its report would provide more information than anyone has so far.

Instructions: How to run the Etrecheck Diagnostic Tool - Apple Community

What happens when you try?

Have seen if the behavior persists while started up in Safe Mode ?

Definitely not the expected behavior. I select quit, and quit happens.

The issue might be the app itself.

How to force an app to quit on Mac - Apple Support

When I right click on icon ( programs are running indicated by the little dot under it ) the little menu shows quick options like quit. In the past this is how I would always quit programs running before I shut down. When I click quit it does nothing.

Last night I booted up and did notice that if I click quit 2 or 3 times it will quit the program. Then after a while it will quit after first attempt. Very strange. I appreciate the responses. I will try in safe mode and see if it does the same. Thanks again.