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I'm an idiot and I've had to update my first few clerkship apps twice already because of minor writing sample errors realized post-submission. What does this look like from the perspective of the chamber's clerks/judge? Do they just print the new one and not mind? Is it frowned upon? Disqualifying in some cases? Is it even worth doing in the case of a minor mistake or stylistic preference?

Updating just the writing sample would get your app thrown out in my judge's chambers, because it just calls attention to the fact you submitted a writing sample that was not error free (and honestly, depending on how minor the error was, it might not even have been noticed, so you're hurting your own chances here).

I'd say definitely don't update. It's good that you haven't suvmitted lots of apps yet; you should go back through your writing sample a few more times and maybe have a friend proof read it for typos (if the judges to whom you're applying allow that).

I second the above. PLEASE everyone, proof your writing samples. I've had so many great candidates get their apps thrown out because of stupid errors in their writing samples.

One person was #1 in her class and the 3rd footnote (on the first page) was "Cite - add in statute about X." I counted over 30 errors in 6 pages of her writing sample before I stopped reading. And these weren't tiny errors like an italicized comma; these were glaring errors like spelling errors, 2-line citations that were entirely italicized, incomplete half sentences, and so on. I don't know how the hell she missed all these errors or, worse, thought that her writing sample was acceptable, but that probably got her cut from so many great opportunities.

This compelled me to re-check all of my materials and I found 1-2 small typos in each. Whether or not that has negatively affected my current (small) number of applications (and it probably has, haha), I'm glad that my future ones will be even better. Live and learn

I wouldn't update. Just hope the error isn't caught. If you update, it will draw attention to the error.

Fix your writing sample for future apps.

I mentioned this in another thread, but I think it's worth repeating here. Sometimes you just luck out. I sent a clerkship application with multiple typos. Didn't mention them; got an offer.