Alert feat in DnD 5E explained

Dungeons & Dragons is the most iconic TTRPG, and it’s chock-full of monsters and creatures who think you’d make a pretty tasty dinner. Here’s why you want this feat. Think of Alert as your caffeinated choice of homebrew drink, combined with a pumped up and [mostly] healthy paranoia that’s actually useful. Let’s break down what makes the Alert feat a player favorite.

You have a permanent +5 to initiative. This has two major benefits: anyone whose character has a low dexterity modifier will get help increasing their chances of scoring a significantly higher initiative than they normally could, and characters with this feat will more than likely end up towards the top of the initiative roll call. Being higher up in the initiative order means you essentially get an extra turn in combat. And you want that in order to maim the baddies as quickly as possible.
You cannot be surprised as long as you are conscious. Okay, so I may have exaggerated a little bit in the intro, but would you rather me kill the imagery? Didn’t think so–I know you eat that up. You do, however, have to be awake for this part of the feat to work. With Alert, the enemy cannot surprise your character, and thus you won’t be rendered helpless on the first round of combat. It’ll just have to move on to the next player character who was foolish enough not to take this feat.
Other creatures don’t get advantage on attack rolls against you as a result of being unseen by you. Whether a baddie can turn invisible, or lucked out and rolled a crit on their stealth roll, they simply aren’t good enough to pull wool over your eyes. No enemy, invisible or otherwise, is able to have advantage on their attacks on you based on not being seen. Your senses are sharper than those of other adventurers who didn’t take Alert. Then again, you really are just too keen to have missed this feat, after all.

Whether your character is naturally paranoid or has been surprised one too many times, Alert is a feat worth taking for newbies and veteran players alike. But before you get too excited, let’s talk about who this feat is most and least useful for.

Alert is most useful for

Assassin Rogues – these are more likely to trigger the advantage part of their Assassinate ability (which happens when they attack a creature that has not acted yet), letting them use Sneak Attack.
Spellcasters who favor control spells – going before the enemy means you can try and take them out of play before they get the chance to hurt your friends (for example, casting Hold Person to paralyze them, or Spike Growth to severely restrict their movement).

Alert is least useful for

Barbarians – these tough fellows will still see some advantages from Alert, but their class already grants a feature (Feral Instinct, 7th level) which allows them to act even if surprised, and gives them advantage on their initiative rolls. This, combined with a reliance on multiple stats, makes an Ability Score Increase harder to give up for Alert.

How to roleplay the Alert feat

Need some help roleplaying the Alert feat? Here are some examples to help you out:

As you traverse the dense forest, you notice a rustling in the bushes ahead of you. Thanks to your keen senses and alertness, you are able to quickly draw your sword and prepare for battle before the hidden bandits can ambush you.
As you enter the dark and ominous dungeon, you feel a chill run down your spine. Your Alertness feat kicks in, allowing you to detect the presence of an invisible lurking monster before it can surprise you. You quickly take cover and alert your party to its presence, allowing you to strategize and plan your attack.
While walking through the crowded marketplace, you suddenly feel someone’s hand brush against your pocket. Your Alertness feat helps you detect the pickpocket’s movement, and you are able to catch them in the act. You confront the thief and retrieve your stolen coin purse, preventing any further theft.
As the party rests in their campsite for the night, you stay up to keep watch. Your Alertness feat ensures that you are always on high alert, and you notice the subtle movement of a group of goblins approaching your camp. You quickly wake up your companions and prepare for battle, preventing the goblins from catching you off guard.
While negotiating with a shifty merchant, you detect a subtle twitch in their body language that indicates they are hiding something. Your Alertness feat helps you catch the deceit and get to the bottom of their true intentions, allowing you to make a better deal for your party.

Out of all the feats, of which there are more than plenty, Alert is a must-have for any player who wants to make themselves an asset to their group. Alert, all in all, is a universally helpful feat, so next time you’re leveling up or creating a new character, make sure to stay alert for this feat. See what I did there? Eh? I bet you didn’t see that coming. You would have, though, if you’d taken this feat as we told you to.

As the dead of night crawls on the sky above, a cloudy mist settles in the overgrowth your group has made camp in. The orc Paladin was certain this would be a good place for a much needed long rest. But you know better: when you sleep, it is with one eye open; when you lead the trail, your senses are always three steps ahead. And now, with the hair on your arm standing on end, and a familiar prescient feeling curling your blood, you know it's time. Time to take the initiative, and maybe, just maybe, take the upperhand from whatever foe mistakenly thought could catch you and your party off guard with sneaky crossbow shot. At least, that's what would happen if you had the Alert feat.