Eventually, I'm going to get used to the fact that the "current rules" of D&D are those found in the 2024 PHB, and thus we can actually talk about True Strike as a good and even potentially really good spell, rather than the utter garbage it was in 2014 (and, notably, it was an entirely different design that served a different purpose).
Shillelagh was always a cool spell for Druids primarily, which admittedly didn't scale terribly well.
But both of these spells have changed somewhat, and also, it's a lot easier to come by either of them thanks to Magic Initiate being an Origin Feat.
I wanted to compare the two and talk about which kinds of builds would want to use them.
Let's just define our terms here:
True Strike is a cantrip available to Bards, Sorcerers, Warlocks, and Wizards. As an action, you make an attack with a weapon used in the casting (the spell, similar to Booming Blade and its ilk, has a material component of a weapon that is worth 1 copper or more so that you don't encounter issues with what the damage die for an amulet should be - though this does break the ability to use it with Shadow Blade), and you use your spellcasting ability rather than Strength or Dexterity for the attack and damage rolls. The weapon can deal either its normal damage or radiant damage, your choice. At levels 5, 11, and 17, you add a d6 of radiant damage when you hit with this.
Shillelagh is a cantrip available to Druids (though Rangers can get it if they take Druidic Warrior rather than a Fighting Style feat). As a bonus action, you take a Club or Quarterstaff and imbue it with natural magic. The weapon's damage die becomes a d8, and you can (note, can) use your spellcasting ability instead of Strength for attack and damage rolls with it. It can also deal force damage or the weapon's normal damage when it hits. At level 5, the damage die for the enhanced weapon becomes a d10, and then at level 11 it becomes a d12, and at level 17 it becomes 2d6.
So, let's boil down the nuances here:
Notably, True Strike does not allow you to use Strength or Dexterity for the weapon's attack and damage rolls. It requires you to use your spellcasting ability. Shillelagh lets you use both.
Shillelagh's damage does technically scale up, but not nearly to the degree that other cantrips typically do. You will be adding your (likely growing) spellcasting modifier, but ultimately, a d8 has an average of 4.5 damage, while 2d6 has an average of 7 - a pretty tiny increase compared with, say, Ray of Frost, which goes from an average of 4.5 to 18.
True Strike scales in a lot of ways in the conventional way, adding a die at each tier of play. However, it also gives you your modifier.
Now, let's think about who these are for.
Obviously, the classes these are available to are the easiest answer to this question, but as we mentioned before, it's not terribly difficult to get either of these. (Indeed, I think you could make a solid argument for taking both, even if there's a bit of redundancy in their overlap.)
As we said before, Shillelagh's damage scaling is pitiful compared with other cantrips. However, Shillelagh, the spell, is not actually the attack itself. And here, we can start to see how character with extra attack might find it more useful.
While its most obvious feature is the "use a spellcasting ability for attacks," I actually think where it might become most useful is in its weapon scaling.
In 5E, both 2014 and 2024 versions, the highest damage die you can get with a simple weapon is a d8, and the highest damage you can get with a light weapon (simple or martial) is a d6. Clubs do only a d4 of bludgeoning damage, but they have the Light property. Thus, casting Shillelagh on a Club actually boosts it by two damage on average immediately. By tier 4, your club is hitting as hard as a maul or greatsword, while still being a one-handed light weapon.
Thus, in this case, I imagine that martial classes would get the most out of this cantrip - for a single bonus action at the start of combat, each of your attacks is doing a lot more. A max level fighter with, say, 21 in Strength, could go from doing (1d4+5)x4, which comes to an average of 30, to (2d6+5)x4, or 48 - a jump of over 50%.
By contrast, True Strike takes up an entire action to use every time you make the attack. At least for most.
Eldritch Knights and Valor Bards have joined the Bladesinger Wizard in now being able to weave a cantrip into their extra attack feature.
The problem for them, of course, is that it will mean that different attacks use a different ability modifier.
Typically, an Eldritch Knight will focus on a physical ability over their spellcasting ability - I know on mine, I favored spells that didn't really care how high my Intelligence was, or were at least pretty effective regardless, like Booming Blade and Shield (Green-Flame Blade does benefit a little from good intelligence, but not by a ton).
I could see it working better for Valor Bards, who are more inclined to pump their Charisma. But they are still left in that awkward position, unless they're boosting both Charisma and... probably Dexterity perfectly evenly.
Thus, True Strike might actually be best in the hands of a focused spellcaster - without Extra Attack, you may as well pump all the potential damage into a single spell per turn.
Of course, it might be best to just get both.
Again, there's some awkward redundancy here, but what this will allow you to do is, if you get a Club or Quarterstaff. While Mastery will play a part for Eldritch Knights, the real question is whether you want to dual-wield or not.
The choice between these weapons is basically whether you want to dual-wield or not. For damage, dual-wielding is certainly a little more potent than using a Quarterstaff, but you might not be trying to maximize damage. For an EK in particular who wants to be very tanky with sword-and-board, the Quarterstaff has the advantage of also acting as a spell focus, meaning if your DM is persnickety about whether you can cast Shield or other spells with your weapon and shield out, you don't need to worry about it. I'd also argue that for a Fighter, the Club's Slow Mastery is a little redundant, as you'll eventually get a feature that lets you use that mastery with any weapon.
Dual-wielding is tricky here, and depends on a couple rules clarifications.
Essentially, what you want is a Shillelagh'd up Club and another light weapon - one with nick if you get weapon mastery. Let's say a Dagger is your other weapon:
The first attack you make is with your Shillelagh Club. Now, as part of your attack action, using your Extra Attack feature, you cast True Strike with the Dagger.
Because you've hit with a light weapon, you can make your extra light-weapon-attack with the other. And because you've used both weapons with your regular attacks, you can make your light-weapon-attack with either of them. And, of course, we're going to do so with our Shillelagh Club, meaning that all three attacks are using our spellcasting ability, and two of them are hitting with higher dice thanks to Shillelagh.
The only question here is whether, if you do get access to weapon mastery, the off-hand (or really the light-weapon-attack, which I'll abbreviate to LWA) has to be made with the Nick weapon. If that's the case, we're kind of SOL for trying to save our bonus action, as neither of the potential targets for Shillelagh have Nick. But still, we can make all those attacks with our spellcasting ability.
Eldritch Knights can go for this as well, if you want to heavily invest in Intelligence rather than Strength. I'd probably want to get at least 15 to wear plate armor (and bump that to 16 with something like the Dual Wielder feat). But I think Valor Bards, who can afford to just bump Dex to 14 and have their best armor class, probably make the most sense for something like this - especially because they have plenty of ways to get all the spells needed once they unlock Magical Secrets.
I will note that pure spellcasters can also make decent use of True Strike. If we assume a +3 for their spellcasting ability modifier, a two-handed Quarterstaff will deal 1d8+3, compared to 1d10 for something like Firebolt, which is 7.5 versus 5.5. At 5th level, if we get a +4 to that stat, we're looking at 12 versus 11. By level 11, if we've maxed our our spellcasting stat, we're looking at 16.5 vs 16.5. It's really only when you hit level 17 that it falls off to 20 versus 22 - but note that if we have a +2 weapon, we're once again on-par.
Shillelagh, on the other hand, because of its extremely modest scaling, really needs extra attack to start feeling impactful
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