I may have tricked you into this thread by implying that I've done this, but I actually need advice here. Sorry about that.

My players have started the slide up the morality ladder into paragon without any difficulty at all, but that's only what spawned the idea, rather than being something I feel I need to solve (plus, I've read quite a few suggestions for fixing or otherwise altering the conflict system). I haven't been putting my players in a lot of tough positions: they are mostly challenged by obstacles rather than meaningful choices and I'd like to change that. Most of the positions they've been in have had a clear noble/ignoble delineation and I'd rather make that harder to see.

I was hoping to get examples of moral quandries or difficult choices you've used in your game or had used on you that were super effective?

I actually had one, though I wasn't planning on it.

One of my players got me a copy of Mask of the Pirate Queen last Christmas, so I promised I'd run them through it. I replaced the Zann Consortium with a criminal organization that had developed during our campaign, one run by a fugitive Jedi. Her goal was to take over the Veiled Sorority and use their resources for a massive Star Destroyer heist which would form the finale for the first half of our campaign. This Jedi-turned-crime-boss asked the PCs for their help; one of them was Force sensitive and had done some training with her, plus she had busted them out of Imperial custody a while back, so they said yes.

The problem was, by doing the crime boss's dirty work, they were considered a part of her organization. At every turn, the Sorority's allies referred to them as part of the "Blood Takers," this criminal syndicate the boss had built. When people heard they worked for this individual, they would cower or spit. It culminated when the first act villain from the module said she had no interest in mercy at their hands, since "the mercy of the Blood Takers is as legendary as it is deadly."

During all of that, the PCs were getting more and more squicked out by their apparent affiliation, which was brought on through a friendship. They felt like they had been tricked, but also that they couldn't back out of the deal since the crime boss had done so much for them. It disturbed them enough that, when said villain refused to surrender, the Force sensitive PC actually refused to continue the fight. They abandoned the job on the spot.

That hadn't been my intention, but I rolled with it. I made it clear that their boss wouldn't tolerate such a break, but she'll see the back of them because of their shared history. However, if they ever cross her path again, all bets were off. Then they were recruited by Wedge Antilles to join the Alliance... in order to pull off their old boss's heist for the benefit of the rebellion.

I'm not sure that all counts as a moral quandary -- there was a pretty clear-cut moral choice to be made. However, it involved some tough decisions, including turning away from a relationship that had previously only been beneficial and then actively betraying that person's interest. My players struggled with the decision for a good few sessions, though I would caution that you don't want to leave them twisting for too long. Otherwise the strain becomes real and the game stops being fun.

You know, lots of little moral quandries are just as effective as the big, obvious ones.

I had my players stow away on an Imperial supply ship that was running equipment to this covert archaeological dig. As they explored the cargo hold the players found crates and crates of all sorts of useful equipment they could just help themselves to... for 1-2 conflict per piece of gear, depending on value and usefulness. Quite a few of them ended that session with around 5-6 Conflict.

There's also the classic "this guy has information you want, but he won't just say it". No need to make it as obvious as torture, just a decent Coercion check will do... but it gives them 2 Conflict, or they'll need to go into the next encounter without information that will prove useful.

Several of my pcs recently had vision quests in order to obtain lightsaber crystals. I attempted to use moral quandary - I don't know if it was super effective, but they are all apparently still coming back for another session. So let's call that a win.

For each pc, their first choice was whether to follow a vision away from the rest of the pcs. Their next choice was a fairly straight forward interaction with the vision (trying to play on their moral strengths/weaknesses). I knew it was all pretty overt/heavy handed, and I really wanted them to think about the final choice, so I did the most overt, heavy-handed thing I could think to do for the final choice - I gave them a choice between three paths. Down one path was someone or something from their past that they loved that needed their help, down another path was something that they wanted, and down the third path were the rest of the pcs, fighting for their lives.

As it was a force vision, I'm hoping to revisit the choices they made in the real life of their characters, because it seemed like they really were torn about how to proceed (some of them, anyway). So I would try this formula, if you can set it up: a selfless choice, a selfish choice, and a choice for the good of the group.

I find if you present things that interest the players, they tend to get into moral quandries all on their own. Example: characters want to grow in their knowledge of the force. You present them with information of relics being kept in a vault on an imperial occupied world.

If they take on this quest, think about these things.

Do they invade & steal the relics just so that they can grow their knowledge and powers? If so, how do they go about it? Do they try to sneak in & be unseen or do they just go in fighting and make an escape? How far will they go to obtain this power? Do they attack Imperials on sight? Do they impose their will on the guards to let them pass? Do they kill? Do they interrogate or strike fear in the hearts of those who currently obtain the relics? Are they willing to give up on this power if it means they can help or save their comrades?

Same thing with stuff like money & equipment. Are they working jobs to get their money or are they stealing their equipment? Do they just steal or are they killing people just to take their items? Are they only motivated by the rewards for a job? Do they ever take the things they steal and give it to those in need, such as the poor, sick, hungry? Do they steal from anyone or do they steal from just wealthy and corrupt organizations like the Empire?

Do they attempt to diffuse situations before escalating to violence as the last option or do they constantly ignite their sabers at every chance? Do they disarm or disable in combat or do they always attempt to kill their opponents? What if the opponent is a big bad and they feel like the only option to permanently stop this big bad is to kill them, however the big bad is no longer a threat and is unable to continue fighting?

There's a lot of quandries that the players may not think are serious decisions. The examples I gave are just stuff that happens as one plays the game. The GM should be tracking all the choices made and whether they accrue conflict, such as attacking first in situations or stealing (even if it's from the Empire!)

As far as BIG moral choices, in movies those are often the ones revolving someone's close relations. Separate the group and capture a PC, force the rest to make choices of whether they will work with criminals & do messed up things to get their party member back or whether they will wait it out until they can figure out a good plan that doesn't involve sketchy business. One could also do a similar thing with recurring NPCs if the one player doesn't want to play the "captive" the entire session.

Other ideas for big moral choices include things involving the player's backstory, choices that involve high stakes, risky decisions & the concept of no good choice, just bad ones.

Referring to the movies, Yoda tells Luke that the Dark Side is the quicker, easier path. So one could present quick & easy solutions to the players to solve encounters or problems, then let them decide to take those or think up better options that don't involve selfish actions.

It's good to remember that choices don't always have to be a binary 2 options of good or bad. The players may very well likely come up with a solution to a problem you could not even think of. It's good to be flexible in that regard, to allow them to attempt things their way.

Example of that: A BBEG found PC's sister who was on their ship with them and captured her. The BBEG gave the PCs a choice: save her and let a city be destroyed or save the city and let her die. A third option was presented by one of the PCs: the BBEG take the sister with him unharmed as collateral against the group and leaves the city alone and the group would stop following him for now. The BBEG accepted, as he now has leverage over all of them and the next time they try to stop him, he can just put her life in the balance once more. It's just prolonging the choice they have to make of stopping the BBEG or keeping the sister alive and means they agreed to let the sister be a captive. Not such a good moral choice but it was better than the alternatives.

It may be that you could just start giving them Conflict for things that you haven't been before, or alter your thinking on what generates conflict in the first place. It may be that if they wish to become and then maintain themselves as Paragons of the Light Side, then they'll have to behave like the much maligned Lawful Stupid Paladin. Is it impossible? No, but being a Paragon of the Light Side should mean limiting your options, discarding any options that are in any way unseemly or ignoble. I would say here that only Yoda might qualify for this from what I've seen of the movies. Most jedi aren't paragons, though they may strive towards that goal. Luke certainly wasn't a Paragon.

I give out small amounts of Conflict but I do it often and continually. Typically speaking, my jedi suffer conflict in any plan they come up with that effectively means an ambush. 1 point for deciding on it, 1 point for enacting it. As has been suggested above, Coercion checks? Conflict. Skullduggery? Conflict. Deception? Conflict. Etc.

If you need a reason for why some actions are suddenly generating conflict when they haven't before, say that the Dark Side has grown in strength lately, and its tempting ways are ever stronger. Heck, the Jedi Council could acknowledge this and send the PCs off as part of a multi-jedi investigation into several suspect locales in order to attempt to identify the source of this corruption.

Perhaps if the PCs are succeeding in their missions without resorting to rough tactics, then it could be that the missions are too easy for them? Mcguffins that are protected by 6 guards who will allow the Jedi to approach and converse are easier than mcguffins protected by 50 guards who will shoot the jedi on sight.