I have the following code that starts up a "tray icon" and adds a NSMenu to it.
#import <Foundation/Foundation.h>
#import <Cocoa/Cocoa.h>
@interface TrayIcon : NSObject
@property(strong) NSStatusItem *statusItem;
- (void)makeTrayIcon;
- (void)stopServer:(nullable id)sender;
- (void)startServer:(nullable id)sender;
@end
and...
#import "TrayIcon.h"
@implementation TrayIcon {
}
- (void)makeTrayIcon {
    // Flycut/AppController.h
    IBOutlet NSMenu *jcMenu;
    // Flycut/AppController.m
    _statusItem = [[NSStatusBar systemStatusBar] statusItemWithLength:NSVariableStatusItemLength];
    [_statusItem setHighlightMode:YES];
    [_statusItem setImage:[NSImage imageNamed:@"16.png"]];
    [_statusItem setMenu:jcMenu];
    [_statusItem setEnabled:YES];
    //Add Menu
    {
        NSMenu *menu = [[NSMenu alloc] init];
        [menu addItemWithTitle:@"Start Server" action:@selector(startServer:) keyEquivalent:@""];
        [menu addItemWithTitle:@"Stop Server" action:@selector(stopServer:) keyEquivalent:@""];
        [menu addItem:[NSMenuItem separatorItem]];
        [menu addItemWithTitle:@"Quit" action:@selector(terminate:) keyEquivalent:@""];
        _statusItem.menu = menu;
    }
}
- (void)stopServer:(nullable id)sender {
    NSLog(@"Stop STUFF");
}
- (void)startServer:(nullable id)sender {
    NSLog(@"Start STUFF");
}
@end
For some reason my menu looks like this.

Why would Quit be enabled but "Start Server" and "End Server" not be? By using @selector(terminate:) on Start/Stop server they become enabled. Perhaps I have bad syntax in my methods startServer and stopServer?
We have similar code, and I removed the -setTarget call and saw the disabled state.
As Willeke stated, it is because your object isn't in the responder chain.
So just make sure you explicitly set the target property:
  NSMenuItem *item = [[NSMenuItem alloc] initWithTitle:@"Start" action:@selector(startServer:) keyEquivalent:@""];
  [item setTarget:self];
  [menu addItem:item];
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