Can the Battle Master’s Ambush Maneuver be used more than once on the same roll?

Question

I am currently running a Fighter 5 with the Battle Master subclass. Later, I plan to multi class 3 levels into rogue, possibly taking the Assassin subclass for the free crit on surprise.

The Combat Superiority trait from the Battle Master states:

When you choose this archetype at 3rd level, you learn maneuvers that are fueled by special dice called superiority dice. You learn three maneuvers of your choice. Many maneuvers enhance an attack in some way. You can only use one maneuver per attack.

(emphasis mine)

The Ambush Maneuver states:

When you make a Dexterity (Stealth) check or an initiative roll, you can expend one superiority die and add the die to the roll, provided you aren’t incapacitated.

As per RAW, would I be able to use this maneuver more than once on the same initiative roll, as it doesn’t require an attack? I am confused if this was even developer intent, as this just seems blatantly overkill to use more than once, except for the purpose of complimenting the Rogue’s Assassin subclass.

(I am aware that this maneuver only allows one superiority die to be expended- is this the cap for the entire roll, or am I allowed to the take the maneuver again? It seems odd that the PHB would specify one maneuver per attack when all maneuvers are capped at one die anyways.)

Answer 1

You can expend one superiority die.

The feature tells you how many superiority dice you can roll:

When you make a Dexterity (Stealth) check or an initiative roll, you can expend one superiority die and add the die to the roll, provided you aren’t incapacitated.

If you were able to expend more superiority die, the feature would tell you. The intent seems quite clear that you can only use Ambush once per check. If the feature was intended to allow more than one die per check, it would have just said that.

Answer 2

As someone has already said, you can only spend one superiority die on the initiative role:

When you make a Dexterity (Stealth) check or an initiative roll, you can expend one superiority die and add the die to the roll, provided you aren’t incapacitated.

However, your question may be about using superiority dice more than once.

There's nothing in the rules that says you can't then spend another superiority die on something else, later in the round (it seems like you may be asking this as well)

Example: It's perfectly within the rules for you to:

• Try and be silent (add one superiority die to your stealth roll)
• Fail the stealth check, resulting in combat
• Try and act first when combat breaks out (add one superiority die to your initiative roll)
• Spend yet another superiority die on your attack (goading attack maneuver?)
• And finally spend one more superiority die later in the same round to do an opportunity attack on an opponent that missed (ripost maneuver)

You just can't add more than one die, and can't use the ability more than once during an attack action (or reaction), but you can burn superiority dice many times over the course of a round.