Why in Android 8 method Settings.canDrawOverlays() returns "false" when user has granted permission to draw overlays and returns to my application?

I ran into the same problem. I use a workaround which tries to add an invisible overlay. If an exception is thrown the permission isn't granted. It might not be the best solution, but it works. I can't tell you anything about the AppOps solution, but it looks reliable.

Edit October 2020: As mentioned in the comments there might be a memory leak inside the WindowManager when the SecurityException is thrown, causing the workaround view not to be removed (even with explicit calls to removeView). For normal uses this should not be much of a problem, but avoid running too many checks in the same app session (Without testing it I'd assume anything below hundred should be alright).

/**
 * Workaround for Android O
 */
public static boolean canDrawOverlays(Context context) {
    if (Build.VERSION.SDK_INT < Build.VERSION_CODES.M) return true;
    else if (android.os.Build.VERSION.SDK_INT >= Build.VERSION_CODES.O_MR1) {
        return Settings.canDrawOverlays(context);
    } else {
        if (Settings.canDrawOverlays(context)) return true;
        try {
            WindowManager mgr = (WindowManager) context.getSystemService(Context.WINDOW_SERVICE);
            if (mgr == null) return false; //getSystemService might return null
            View viewToAdd = new View(context);
            WindowManager.LayoutParams params = new WindowManager.LayoutParams(0, 0, android.os.Build.VERSION.SDK_INT >= android.os.Build.VERSION_CODES.O ?
                    WindowManager.LayoutParams.TYPE_APPLICATION_OVERLAY : WindowManager.LayoutParams.TYPE_SYSTEM_ALERT,
                    WindowManager.LayoutParams.FLAG_NOT_TOUCHABLE | WindowManager.LayoutParams.FLAG_NOT_FOCUSABLE, PixelFormat.TRANSPARENT);
            viewToAdd.setLayoutParams(params);
            mgr.addView(viewToAdd, params);
            mgr.removeView(viewToAdd);
            return true;
        } catch (Exception e) {
            e.printStackTrace();
        }
        return false;
    }
}

I've found this problems with checkOp too. In my case I have the flow which allows to redirect to settings only when the permission is not set. And the AppOps is set only when redirecting to settings.

Assuming that AppOps callback is called only when something is changed and there is only one switch, which can be changed. That means, if callback is called, user has to grant the permission.

if (VERSION.SDK_INT >= VERSION_CODES.O &&
                (AppOpsManager.OPSTR_SYSTEM_ALERT_WINDOW.equals(op) && 
                     packageName.equals(mContext.getPackageName()))) {
    // proceed to back to your app
}

After the app is restored, checking with canDrawOverlays() starts worked for me. For sure I restart the app and check if permission is granted via standard way.

It's definitely not a perfect solution, but it should work, till we know more about this from Google.

EDIT: I asked google: https://issuetracker.google.com/issues/66072795

EDIT 2: Google fixes this. But it seem that the Android O version will be affected still.

Here is my all in one solution, this is a combination of others but serves well for most situations
First checks using the standard check according to Android Docs
Second Check is Using the AppOpsManager
Third and final check if all else fails is to try to display an overlay, if that fails it definitely aint gonna work ;)

static boolean canDrawOverlays(Context context) {

    if (Build.VERSION.SDK_INT > Build.VERSION_CODES.M && Settings.canDrawOverlays(context)) return true;
    if (android.os.Build.VERSION.SDK_INT >= android.os.Build.VERSION_CODES.M) {//USING APP OPS MANAGER
        AppOpsManager manager = (AppOpsManager) context.getSystemService(Context.APP_OPS_SERVICE);
        if (manager != null) {
            try {
                int result = manager.checkOp(AppOpsManager.OPSTR_SYSTEM_ALERT_WINDOW, Binder.getCallingUid(), context.getPackageName());
                return result == AppOpsManager.MODE_ALLOWED;
            } catch (Exception ignore) {
            }
        }
    }

    try {//IF This Fails, we definitely can't do it
        WindowManager mgr = (WindowManager) context.getSystemService(Context.WINDOW_SERVICE);
        if (mgr == null) return false; //getSystemService might return null
        View viewToAdd = new View(context);
        WindowManager.LayoutParams params = new WindowManager.LayoutParams(0, 0, android.os.Build.VERSION.SDK_INT >= android.os.Build.VERSION_CODES.O ?
                WindowManager.LayoutParams.TYPE_APPLICATION_OVERLAY : WindowManager.LayoutParams.TYPE_SYSTEM_ALERT,
                WindowManager.LayoutParams.FLAG_NOT_TOUCHABLE | WindowManager.LayoutParams.FLAG_NOT_FOCUSABLE, PixelFormat.TRANSPARENT);
        viewToAdd.setLayoutParams(params);
        mgr.addView(viewToAdd, params);
        mgr.removeView(viewToAdd);
        return true;
    } catch (Exception ignore) {
    }
    return false;

}