Is the Alert Feat better than an Ability Score Improvement for a Rogue?

Question

I'm close to getting a 4th level of Assassin Rogue with a character I'm playing and I'm torn between picking up the Alert feat or improving an Ability Score (i.e. +2 Dexterity) so:

Which is best, an Ability Score Improvement or the Alert feat for my Rogue?

Obviously the main ability scores are important, but the potential is there for me to ignore ability score increases entirely and focus on feats exclusively.

The Alert feat, in my opinion, gives some great advantages for almost any class:

• You gain a +5 bonus to initiative
• You can't be surprised while you are conscious
• Other creatures don't gain advantage on attack rolls against you as a result of being hidden from you.

The initiative bonus is pretty self explanatory - a high Dex character gets a decent shot at going before almost everyone or it could mitigate unlucky rolls.

Practically never being surprised is also a huge plus - you can react to, and potentially even negate, ambushes and sneak attacks against the party.

Finally, preventing advantage on attack rolls against you from hidden characters removes a huge portion of an attacking Rogue's potential to sneak attack your character as well as reducing the chance of actually being hit by all hidden attacks. At worst, if someone gets advantage against you, you'll probably have seen them coming first.

Combining this Feat with the Rogue's Assassin lvl. 3 feature (which my character has) seems even better:

Assassinate

Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

The bonus to initiative gives you an even higher chance of consistently getting a sneak attack in combat and an auto-crit on the first sneak attack of an ambush can cause huge damage, potentially ending the combat before it even begins.

All of these advantages make me think the feat is superior to the benefits of +2 Dexterity (or another Ability Score Increase).

Personally I don't think the extra +1 AC from +2 Dex (for example) is as good as the benefits of this feat, especially with 5e's bounded accuracy, but I could be persuaded otherwise...

(Edit: My question isn't aimed at discussing which feats are the best. But even so, this feat seems to be one of the best in the PHB and a fairly solid choice for almost any class...)

Answer 1

Here's what you're trading for the alertness feat if you don't take the abil score upgrade and instead take the feat:

• +1 to damage
• +1 to hit
• +1 to AC
• +1 to Dex saves
• +1 to Dex checks
• +1 to init

The question then, ultimately, becomes, is +5 init (net +4), no surprise and no advantage on attacks against from hidden opponents worth it.

The latter two features are very dependent on your campaign and DM. Surprise should be a fairly frequent occurrence on both sides of combat, but that still depends on how willing your DM is to allow it or stage his monsters to have them obtain it (and kind of how cautious your group tends to be). Monsters attacking from hidden is another one that really depends on your DM, you group and how well you guys are at nosing out monsters from the shadows.

So ignoring those two items since they are DM and campaign dependent (and thus can't be weighted objectively), the question then becomes, is +1 to Dex more or less beneficial over 4 levels than +5 to init.

For pretty much any character other than the Assassin Rogue, I'd probably argue that they should take the stat upgrade early, the feat at L8 and then the last stat upgrade. However +5 init has amazing synergy with the Assassin Rogue and you're going to get a ton of mileage out of it.

If you're already at 20 Dex (if you managed to start at 20, or 18 and are at L8), then there really isn't any stat upgrade that is worth taking over this feat (though there may be better feats). Rogues are skill monkeys, yes, but +5% in a single ability set of skills is not worth the +25% to initiative and other features o this feat. The only one that would be worth considering at all is Con for the extra HP, but it's really not that many and you're better of boosting your damage significantly.

Take the feat at L4 (or even better, play a human and take it at L1).

Answer 2

What it boils down to is math. The alertness feat in the case of Assassin Rogue is better. The other classes and class options can all be the same. For example: Dual Weilder, by itself for classes without the Two weapon fighting style is bad. But once you take Dual Wielder and the style you now have an extra attack with a normal non-light weapon as a bonus action PLUS your full ability mod(probably +3 or better) So you would have 2 attacks at 1d8+3. On top of this, you receive a +1 AC, and can draw both weapons at once(a DM specific thing really). So the question is not whether feats are better than the flat ability increase, but instead which ones are better for your class/race combo.

Some more combos include but are not limited to: Lucky with just about any class/race, Observant with anyone who will be disarming traps( the +5 to your passive perception pretty much reduces the needs to actively search for traps of your exp tier or lower), and then some that are DM dependent like my favorite: Sharp Mind, which alleviates the need to come up with excuses as to why your character remembers weird things that might make a difference in the story/rp'ing such as; what color the hat that the prince was wearing at a feast 3 weeks ago or some such nonsense. While a lot of players take notes that does not give a reason as to why their character with 8 int could remember such trivial details.

This become especially important if your DM allows the alternate Human stats in the PHB. This is the one that lowers the bonus to only +1 in 2 stats instead of all, but you get a skill proficiency and a feat. A first level human fighter then becomes disturbing when you think about the fact he could perform the above Feat + Fighting Style at first level.

Answer 3

It is a good feat, but really, aside from the +5 initiative (which, if you have a high DEX, may not be all that necessary) the rest of the feat only applies if the DM sets up encounters that it can exploit. Is your party ambushed often? Are enemies often using stealth against you? If so, then the feat is very valuable, if not then ability score increases may serve you better.

If the rogue is point man then the feat might help him, but if he has no way of passing word back to the rest of the party (or the ambush affects them as well) then they will still be surprised. I would also rule that while the Alert PC can negate the advantage from attacks by a hidden enemy, he still doesn't know where those enemies are UNTIL they attack (he can just kinda dodge the attack), so the feat has less benefit than you might think, and certainly doesn't help the rest of the party avoid those attacks.

So an extra +2 WIS with the correlating +1 in passive perception might be more useful, especially as that will help with traps and will help DETECT hidden opponents so you can call them out to the rest of the party.

Answer 4

I would like to point out that both the players hand book and the dmg states you can train feats during down time, where as Ability Improvement scores you can not train during down time. so if you find you get a week here and a week there of down time and your DM remembers to give you cash rewards or that the world has a decent amount of wealth that you can obtain then take the improvement.

If you find your group is constantly running from task a to task z with no break time. well then buckle up cause your really going to have to weight the two cause you only get 4 improvements/feats(or 7 for fighter; and less then 4 for multi-class in some cases)

just remember that feats are better to grab later game usually if you cant train and you should be aiming for higher stats at first if you can.

also as a player grabbing a couple lvls in other class for a feature can be just as fun if not beneficial to you as grabbing a feat or ability improvement.

Fighter with 3 lvls of barb or ranger can give you resistance, dmg buff, spells. a rogue with 6 lvls of monk can give you Shadow teleportation/hiding.

one of my favorites is paladin with two lvls of wizard (divination) for some fun shenanigans(replace a d20 with one of 2 previously rolls d20's on anyone you can see plus rituals like identify and detect magic for magic looting.

Answer 5

Tommy, I like you taking the alert feat for the assassin rogue just for the synergy with the assassinate ability. It has a cool build factor that goes beyond just the numbers. The defensive benefits are added gravy. In my experience when I build with "cool factor" in mind the characters are more enjoyable to play and more memorable for other players. It is a role playing game, go for the cool and enjoy the ride.