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The title really says it all. Are you able to Ready an action and then use Action Surge to Ready another? If so, can you be waiting for either of two different triggers to occur?

Action Surge: Starting at second level, on your turn, you can take one additional action on top of your regular action and a possible bonus action. Once you use this feature, you must finish a short or long rest before you can use it again. Starting at 17th level, you can use it twice before a rest, but only once on the same turn.

Ready Action: ...You can take the Ready action on your turn, which lets you act using your reaction before the start of your next turn. First, you decide what perceivable circumstance will trigger your reaction. Then, you choose the action you will take in response to that trigger, or you choose to move up to your speed in response to it... When the trigger occurs, you can either take your reaction right after the trigger finishes or ignore the trigger. Remember that you can take only one reaction per round...

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Yes, but you can only act on one of them

Action Surge allows you to:

take one additional action on top of your regular action

There are no restrictions on what you can do with this action, so taking the Ready action qualifies.

Taking the Ready action spends one action but there is nothing preventing the use of a second action to take another one on the same turn (assuming one is available).

However, since you only have one reaction to spend, you can only respond to one of the triggers and thus only use one of the Readied actions.

However, it is worth noting that this is likely a waste of an Action Surge most of the time seeing as only (at most) one of the two Actions you used will actually result in something happening. It might be worth it in some niche situations (maybe two different life-or-death triggers that you need to cover), but likely you have better uses for your Action Surge a vast majority of the time.

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  • \$\begingroup\$ It may be worth noting that it's good for covering bases. when A or B will happen, you can ready actions for both. \$\endgroup\$
    – tuskiomi
    Commented May 10, 2018 at 23:45
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    \$\begingroup\$ Instead of using AS for two prepared actions, depending on their overlap, you may be able to word one reaction to handle both. Depending on the GM, you might even get away with tracking two different unrelated trigger/response pairs with a prepared action. \$\endgroup\$
    – CAD97
    Commented May 11, 2018 at 4:19

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