KVO – How to check if an object is an observer?

[…] is it possible to check if an object actually is observing that
property?

No. When dealing with KVO you should always have the following model in mind:

When establishing an observation you are responsible for removing that exact observation. An observation is identified by its context—therefore, the context has to be unique. When receiving notifications (and, in Lion, when removing the observer) you should always test for the context, not the path.

The best practice for handling observed objects is, to remove and establish the observation in the setter of the observed object:

static int fooObservanceContext;

- (void)setFoo:(Foo *)foo
{
    [_foo removeObserver:self forKeyPath:@"bar" context:&fooObservanceContext];

    _foo = foo; // or whatever ownership handling is needed.

    [foo addObserver:self forKeyPath:@"bar" options:0 context:&fooObservanceContext];
}

- (void)observeValueForKeyPath:(NSString *)keyPath ofObject:(id)object change:(NSDictionary *)change context:(void *)context
{
    if (context == &fooObservanceContext) {
        // handle change
    } else {
        // not my observer callback
        [super observeValueForKeyPath:keyPath ofObject:object change:change context:context];
    }
}

- (void)dealloc
{
    self.foo = nil; // removes observer
}

When using KVO you have to make sure that both objects, observer and observee, are alive as long as the observation is in place.

When adding an observation you have to balance this with exactly one removal of the same observation. Don’t assume, you’re the only one using KVO. Framework classes might use KVO for their own purposes, so always check for the context in the callback.

One final issue I’d like to point out: The observed property has to be KVO compliant. You can’t just observe anything.

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