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Why didn't Dumbledore ever teach or suggest the usage Legilimency to the members of the Order of the Phoenix, for investigative purposes as well as an advantage against the Death Eaters during duels? Surely, he would have thought of it, as in the Half-Blood Prince, the summary of the book says that the war against Voldemort and his army (Death Eaters and creatures) was not going well, and that the Order has already suffered losses (such as Sirius Black, a skilled duelist who held his own against Dolohov and Bellatrix, the most powerful Death Eater). Why didn't Dumbledore teach Legilimency to the Order of the Phoenix members as well as the Golden Trio (Harry Potter, Ron Weasley, Hermione Granger) when they were constantly battling Death Eaters and trying to find out more info on how to beat them and needed all the advantages against them?

An example would be Borgin and Burkes. We see in the Half-Blood Prince film, I don't know about the novel, that Death Eaters entered their shop. Arthur Weasley sent an agent there, as he told Harry during the Christmas and New Year Holidays. If the agent performed Legilimency, the agent may have learned not only of the purpose of why Draco wanted to mend the Vanishing Cabinet, but also possibly where the Vanishing Cabinet in Borgin and Burkes leads to (Hogwarts Room of Requirement). This would have allowed Dumbledore, via their relationship in the Order of the Phoenix, to shut off, via a destructive spell like Bombarda or Incendio, the Hogwarts Room of Requirement Vanishing Cabinet, and prevent the break-in that caused the Battle of the Astronomy Tower.

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    When is it said that being a Legilimens is helpful in a battle? Yes, being able to predict your opponent's move is handy, but if requires a good bunch of your own focus aren't you putting yourself at more risk?
    – Jenayah
    Commented Mar 20, 2020 at 22:18
  • @Jenayah, ok, that mostly answers the battle advantage of Legilimency. What about the investigative side, such as when you're tracking (under the Disillusionment Charm, Muffliato, and other defensive spells) Death Eaters in dark places that they might possibly visit, like Borgin and Burkes, or the giants? Useful information can be gathered from Borgin and Burkes, because they had half of the Vanishing Cabinets that made up the Borgin and Burkes / Room of Requirement Vanishing Cabinets pair. Maybe Arthur Weasley could have reported this to Dumbledore and prevent the Death Eaters from entering.
    – Kyle V
    Commented Mar 20, 2020 at 22:22
  • Dunno. Will probably take someone more willing than I am to dig up how Legilimency works and if it could be used that way :) (though IIRC, giants have some natural higher protection against magic, spells and the like)
    – Jenayah
    Commented Mar 20, 2020 at 22:24
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    Was Dumbledore even concerned about battle magic? Seems like he had the OOtP mostly on guard detail and some information gathering here and there. I am not convinced he actually wanted any one to fight/duel at all. His entire plan seems to be to get Harry to horcrux hunt, and have everyone else more or less act as distraction/support as needed.
    – Zoredache
    Commented Mar 20, 2020 at 22:32
  • @Zoredache but if the Death Eaters were rounding up the Order members, how would everyone in the Order support Harry as needed if they were restrained by the Death Eaters?
    – Kyle V
    Commented Mar 20, 2020 at 22:37

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To the best of my knowledge, no direct canon (HP books or movies) answer exists. As for possible reasons, we can either look into the nature of legilimency - it is not quite clear whether or not it is actually legal to perform (certainly some uses of magic are varying degrees of regulated to straight up illegal), it is not clear whether its usage is considered moral by the wizarding community leaving legality aside (most Order members were idealists, with Dumbledore himself, Moody and arguably Snape being notable exceptions). As such, it is quite possible that Order members would've refused to learn or use it even given the opportunity, and it is possible that Dumbledore did not go around spouting about his mind reading prowess for that reason. Equally possible is that Dumbledore's usage of Legilimency was on a strict need to know basis for tactical reasons. It is further possible that Legilimency is just too hard for Order members to perform, at least in a covert way - again, it's not spelled out out anywhere, but the fact that all known users of Legilimency were notable geniuses and would be classed anywhere from morally ambiguous to straight up evil (even in the spinoff movies there is a Legilimens whose abilities are explicitly noted as unusual who ends up joining the wizarding Hitler equivalent) is some circumstancial evidence for these possibilties.

A distant possibility is that Legilimency actually was a skill that some or even most other Order members possessed, but it simply wasn't mentioned and didn't end up being as useful as you thought it would be, either due to possible targets having Occlumency skills to match the average Legilimency practicioner, or that the average Legilimens just can't get such precise mind readings - as Snape says in his introduction on the topic:

It is true, however, that those who have mastered Legilimency are able, under certain conditions, to delve into the minds of their victims and to interpret their findings correctly

That's a lot of hedging. We could read this as Snape just being overly precise just to be a snark, but it's quite possible that the average Legilimency user just wouldn't be able to get results comparable to those we see from Snape, Dumbledore or Voldemort.

TL;DR it's probably either too hard or too neutral evil or a mix of the two.

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