I finally found the answer to this problem. It comes from the way I was setting 
the relationship. I was calling:

  [[expense valueForKey:@"tags"] addObject:tag];

..which apparently is too direct. What I need is something more like:

  [[expense mutableSetValueForKey:@"tags"] addObject:tag];


I discovered the answer as I was preparing to post my question on Stack 
Overflow. It was yet another case of trying to anticipate all the obvious "did 
you try this" responses, and finding the answer myself in the process.

On Jul 10, 2010, at 9:03 AM, David Catmull wrote:

> In my finance app, I have Expense and Tag entities with many-to-many 
> relationships to each other. But changing those relationships doesn't mark 
> the document as dirty, and the changes don't get saved. It doesn't seem to 
> matter if the relationships are optional or not, and they're not transient. 
> This is the first time I've had trouble with object relationships. What could 
> be causing it?
> 
> The project is on GitHub if you want to try it out:
> http://github.com/Uncommon/Budget-Machine
> 
> -- 
> David Catmull
> uncom...@uncommonplace.com
> http://www.uncommonplace.com/
> 


-- 
David Catmull
uncom...@uncommonplace.com
http://www.uncommonplace.com/

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