English Translation
He came even though I told him not to.
This is another example where the subjunctive came as a surprise.
Any “trigger” I could have recognized?
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In the page from Treccani for nonostante, you will see its use as a conjunction referenced in section 1.b. -
Come cong. (con il verbo al congiuntivo), è in genere seguito da che , il quale può anche essere sottinteso
So, for this type of use it is followed by the subjunctive, and it may or may not be followed by che.
Here is another page from Treccani which talks about whether to use nonostante che or nonostante.
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Well, I don’t know Italian. Sorry. lol (but one day I want to starting learning it, I love the sound of it!)
There’s a movie I watched a little. It’s on Showtime and Hulu. “Our Ghosts”. It has a 90% approval rating on Rotten Tomatoes. It’s an Italian film. They speak Italian and the English subtitles are shown below. Thought I’d mention that…
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Ah, you should learn Italian. It has flavour and yes, it is music to the ear 
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From Soluzioni: A Practical Grammar of Contemporary Italian, Fourth Edition: “The imperfect subjunctive is used after past tense main verbs to say what was happening at that time. It may also refer to the future, sometimes after a conditional main verb.” The text had four examples for a past tense main verb:
Avevo l’impressione che lui fosse depresso
I had the feeling he was depressed
Aveva intenzione di pulire la casa prima che arrivasse la suocera
She meant to clean the house before her mother-in-law arrived
Ho insistito che scrivessero subito alla nonna
I insisted that they should write at once to their grandmother
Avevo sempre pensato che la parrucchiera fosse straniera
I had always thought the hairdresser was foreign
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Just a comment regarding possible “triggers”, short of knowing about nonostante.
There are two elements that might hint at the subjunctive:
- a relation of anterioriy between the clauses
- the presence of a concessive clause
Then concordance in Italian is complex and there are probably cases where the indicative or other modes are appropriate in a similar context.
Not sure if this helps 
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E’ venuto, anche se gli avevo detto di non farlo.
Counterexample !
I guess you just have to know the conjunctions…
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Once again, thanks to all of you for helping me along.
But special thanks to @zzcguns because I never thought about the “nonostante / nonostante che” difference and that would have been exactly “my trigger”.
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