Charmed, I'm Sure

Humility difficulty does NOT count towards this achievement. You must absolutely be on Wisdom Difficulty in order for this achievement to register. I learned this the hard way and ended up wasting charms.

2023. The fights are easy. When you defeat these bad boys in the various Trials for the first time you are rewarded items. The 5 Charm Blueprints should drop from bosses in the Trial of Courage & Trial of Loyalty. Once you have the blue prints head out to the crafter. Hopefully you have the ingredients and can craft all 5 charms
Head back in.
Chose a toon. I usually go with Pelegos
Right click on the 5 charms so they appear on your buff screen (me its top right)
Select an opponent
Then select the 'Trial of Wisdom'. Third level
Enter the battle. Win = achievement should pop as your 5 charms are active

I strongly recommend doing this achievement on azaruux as you will need charms to get Personal Nightmare achievement anyway. I attached my guide to help with this.

This is an easy fight. I also did charmed I'm sure for this as the charms greatly help with this achievement

Boss Abilities
Devouring rift. The boss will summon a rift on your location you will see a blue swirl beneath your feet. It will detonate and become an orb that spins around slowly and will explode in a line
Infestation. The boss will summon four adds. You will see these with 4 swirls they explode when summoned and explode when they die make sure to avoid these. They can be killed using unleash very easily or they can be kited to the rift which suck them in and kill them.

For wisdom he gains engorged slam which is a frontal slam that can be easily avoided by sidestepping and creating distance from boss.

Boss strategy
You will need to choose Pelagos and phial of serenity. This will give you extra heals when you need it. Use test of faith to dps boss when it is safe. Aspirant's binding to keep him at a distance and take the shield from confront memories to negate damage. Kill adds with unleash when they are up. Avoid his devouring rifts.unless you are kiting adds into them.

For wisdom I also recommend getting the rifts in the center as this is much easier to get his adds sucked into the rifts compared to rifts around the outside.

For wisdom with Pelagos with Charmed I'm sure and Personal nightmare achievement
His new ability is engorged slam which is a frontal slam that can easily be avoided and can be used to create separation between you and the boss.
https://www.youtube.com/watch?v=nYJmBe09Q7I