Full spoilers for both of these Season 3 Star Trek TNG episodes:
Season 3 Episode 14 “The High Ground”
In this episode the Enterprise is on a “mission of mercy” to deliver medical supplies to Rutia IV a planet which nominally has a planetary government, but which is dealing with an insurgency from a group called the Ansata who clearly view the planetary government has a colonialist entity.
While Cpt Picard, Dr Crusher and a few others are relaxing in a cafe after the delivery there is a bombing. Picard orders everyone to beam up to the ship but Crusher insists on staying behind to treat the wounded. She is captured by Ansata members using personal teleporter technology.
At this point the perspective splits in two, following Crusher as she lives with and learns about the resistance movement, as well as other crew of the Enterprise talking to the head of security forces in the occupied continent, and brainstorming how to get Dr Crusher back.
In the Dr. Crusher scenes, you learn that the planetary government has wiped out whole cities regularly tortures people, and killed the leader of the resistance movement’s 13-year-old son while he was in detention, but considers the guerrilla actions/asymmetrical warfare of the resistance to be terrorism, which apparently Starfleet agrees about?
Data and Picard have a conversation in which Picard states that terrorism is never justified and that he doesn’t believe that “Political power grows out of the barrel of a gun” 
and Data points out that sometimes a political movement has no other viable choices, and that “terrorism” has successfully achieved political aims in the past, mentioning a couple of examples including the 2024 unification of Ireland 
. Side note episode was produced while the Troubles were ongoing and did not air in the United Kingdom or Ireland to my understanding, and wasn’t available completely unedited until the mid-oughts in the United Kingdom.
The Enterprise crew works with the Rutian of security, who hints that she would like to have access to Starfleet weapons to put an end to the war, and they say no because they consider themselves neutral in this conflict, but do agree to help her track down the until now hidden headquarters of the Ansata rebels in an attempt to rescue their doctor.
Crusher and Kyril Finn, the leader of the Ansata have a discussion where he points out that using violence to accomplish your political aims is only considered terrorism by the people in power when their enemies do it, or by historians when documenting failed attempts to gain power. He compares himself to George Washington which feels unfair to the Ansata to me, because as far as I can tell none of them are pro-slavery. Beverly is offended and defends Washington against being compared to these objectively better people (
TV show after all).
She claims that Starfleet is neutral in all this, but he points out that by trading with the Rutian government, especially providing medical supplies only to their side of the conflict (she is a bit disdainful of the fact that the Ansata stole some of the medical supplies for their own wounded) they’ve involved themselves.
Eventually they use their personal teleporters to try to blow up the Enterprise, to draw the Federation into war with them, because they believe that they will have an easier time negotiating, if the Federation is a third chair that negotiating table. But are unable to detonate the bomb before it’s teleported into space. They do capture Picard during the attempt.
After this, the Enterprise crew and the colonial government conduct a raid on the Ansata Base that Enterprise has located. During the raid Kyril Finn is murdered by the head of Rutian security, which the Enterprise crew objects to but does nothing to punish, she says that as a prisoner he would have generated violence, but she believes that as a martyr the violence will calm down. This seems backwards to me just from a practical standpoint?
Regardless, a teenager who is a member of the resistance picks up a laser rifle and points it at the head of security, but the Enterprise crew convinced him to put his gun down, at which point Rutian soldiers arrest him and haul him away, presumably to torture him to death in detention like they did to Finn’s son.
A Starfleet officer opines that maybe this is how peace starts, with one boy putting down his gun. Of course, this ignores that the colonialism that precipitated all of its violence is no longer being resisted presumably?
Overall, this episode strongly reminded me of the current genocide in Gaza, and fortified. My opinion that actually Starfleet is not that good. Lying to themselves about being neutral in an imperialist struggle while materially supporting the imperialists and helping to track down the resistance is pretty disgusting.
A second episode that recently left a mark,
Season 3, Episode 16 “The Offspring”
Data gets back from a robotics conference, and ensconces himself in his lab for a while. Eventually, he reveals that he has created a new Android with a positronic brain, who he has named Lal, which apparently means “Beloved” in Hindi.
Lal has a strangely featureless face, and no genitals. This is because Data is a very good father, and plans to allow his child to choose their own gender and appearance.
Several different heartwarming and or wacky events occur throughout the episode, due to Data’s daughter (she chooses to be a female human) lacking experience with human culture, and basic knowledge of the world around her, while Data spins the episode raising her and asking Beverly Crusher for parenting advice.
Eventually some piece of shit admiral from Starfleet (again, Starfleet bad, kinda) comes along and demands that Lal be handed over to Starfleet Research to be raised. This causes a big conflict because, at this point in the show we’ve already established that Androids are people with the full rights and freedoms of any other member of the Federation. As a result, this is essentially breaking up a family for absolutely no reason, and Lal, having developed emotions, becomes terrified of the thought of being separated from her father causing a cascading positronic brain failure. Data tries to repair her brain, but is unable to do so and spends her last few moments attempting to comfort her. She tells him that she loves him, and he says that he wishes he could share the feeling. She tells him that she will feel it for both of them. At this point I started sobbing. Shortly after Data tells the rest of the bridge crew that his daughter has passed. Give him their condolences, but he states that she’d made such an impact on him that he could not consign her to oblivion, and transferred her memories into his own.
I don’t think this one would have hit me as hard before I had kids, but at this point in my life it’s gut-wrenching.
On a lighter note, there is a scene where she’s observing flirting while working Guinan’s bar trying to learn about human social interaction. When Rokwr walks into the bar, she picks him up from behind the bar and gives him a kiss, and at this exact moment Data also walks in, witnesses the scene and asks Riker “What are your intentions with my daughter?” This was pretty funny.
Felt the same way about both of these episodes when I watched them. The High Ground was such a disappointment, even as a lib when I first watched it I was appalled at how obviously morally superior the resistance was and shouting at the screen why the Enterprise wasn’t helping them. Picard is uncharacteristically naive when he says that shit about political power - just in this season alone Picard himself has solved about a half dozen problems using the implied threat of the Enterprise’s weapons to enforce his diplomacy!
There are a bunch of other episodes that provide better templates with how this conflict could have been approached, too. Maybe the Enterprise crew recognize the moral superiority of the resistance, but their hands are tied by Federation neutrality and they have to find a clever way to save Crusher without helping the space cops. Maybe the Enterprise crew arrives on the planet having only read propaganda about the conflict, but realize over the course of the episode that the resistance is completely justified. Maybe Picard comes up with a clever solution that doesn’t technically break the rules but also massively supports the resistance. Anything but what we got damn.
The Lal episode hit me hard too and I don’t have kids. The show approaches the subject matter so earnestly, even if some aspects of it are goofy you really can’t help but be strung along on Data’s emotional roller coaster. This was the episode where I realized that Data definitely has feelings but he’s convinced himself that he doesn’t.
Maybe the Enterprise crew arrives on the planet having only read propaganda about the conflict, but realize over the course of the episode that the resistance is completely justified.
Wasn’t that the basic plot of “Ensign Ro”? I will give credit to the writers for how they had Picard explicitly say in the opening scene how he doubted that the Bajorans would accept more platitudes instead of real help.
I like all of your High Ground suggestions much better than the actual episode. Ironically the episode right before it was about a planet of nerds who wanted to join Starfleet and the conflict centered around how their military was made by chemically modifying some of their citizens, along with psychologically conditioning them, (All without explaining exactly what was being done, or that it was as far as they were aware permanent) so they’d be more likely to engage in violence and survival situations, and better at it. Once the war was over they confined all of them to a prison colony on the Moon, because they were too scared of their soldiers to allow them to exist in normal society, and had decided that it would be too resource intensive to research ways to reverse the conditioning.
The episode ended with Picard and company beaming away from the head of planetary government who was being held at gunpoint by a number of these soldiers who had escaped the prison colony, and telling him that if his government survived the night, they’d be happy to reconsider their application to join the Federation in a few years.
Picard is absolutely willing to accept the violence is sometimes necessary part of political struggle, but not when the violence is performed by Palestinian/Irish/really just not Western hegemonic coded people.
This was the episode where I realized that Data definitely has feelings but he’s convinced himself that he doesn’t.
I’ve been saying that about Data for a while now. He was sad when his lover died at the end of S1 for God’s sake, that’s a feeling. He clearly has affection for a lot of people, and worries about his desires not being respected and his frustration with his inability to understand human emotions it’s all feelings.
EDIT: also forgot to say, apparently a lot of people were upset at how sympathetically the “terrorist” Ansata were portrayed in The High Ground which just floored me
