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I would like to know if it's possible to do this.

With the Shield Master feat:

  • Turn 1, shove prone with shield, grapple with free hand

  • Turn 2, put away shield while maintaining grapple

  • Turn 3, unsheathe a weapon and attack prone target with advantage while maintaining grapple

The real question is that considering that the shield is armour, is it possible to put it away without breaking a grapple?

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Yes, there are no rules stopping you from putting away your shield.

On top of answering the question, I just wanted to check your order of events to make sure you understand them.

Turn 1: You may only shove a creature prone with your shield as a Bonus Action using the Shield Master feat after you take the Attack Action (Which may come before or after the ACTUAL attack given when you take that Action). No problems here. To make a Grapple, you must forgo one of your attacks in place of a grapple as per PHB pg. 195 Grappling is not a free action. So make sure you either shove first as a Bonus Action and then attack; or you have the Extra Attack feature so that you may follow your grapple up with an attack in the same turn.

Turn 2: PHB pg. 144 tells us that a shield is carried in one hand, and PHB pg. 146 tells us it takes an action to drop, un-equip, or otherwise put away (or Doff) that shield. I don't see anything stopping you from doing this while maintaining the grapple with a free hand as per the grapple rules. No problems here.

Turn 3: As per PHB pg. 190 you can draw a weapon as part of the same attack action using that weapon, and since the target has 0 speed because it is grappled it has never been able to get up from the Prone condition you knocked it into at the beginning of all this. As long as you are using a 1 handed weapon in your free hand, you are still able to make attacks while maintain a grapple with your free hand. No problems here either.

All in all, as long as you have the required number of attacks, this is a considerably effective strategy at keeping a prone target down and suffering attacks from you and your friends.

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  • \$\begingroup\$ Just some nitpicks: (1) Having declared that you're taking the Attack action this turn, you're allowed to take the Shield Master's bonus action to shove first. So shove followed by grapple doesn't require Extra Attack. (see rpg.stackexchange.com/questions/51525/…) (2) Drawing a weapon is not part of the same attack action using that weapon. It's your (one) free object interaction for the turn. \$\endgroup\$
    – Sebkha
    Sep 23 '16 at 0:20
  • \$\begingroup\$ @Sebkha I must have read those as separate paragraphs, with the free object interaction. So drawing your weapon is that same object interaction. I also didn't realize my phrasing implied I thought different about the bonus action shove, and assumed the character was attacking and then shoving. I have rephrased. \$\endgroup\$
    – Airatome
    Sep 23 '16 at 1:37
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    \$\begingroup\$ Can you use an Attack action to doff a shield? From the Extra Attack class feature, you get an extra attack only if you take the attack action. This uses you action, thus you would not have an action to Doff the shield unless you had an ability that gave you an extra action like action surge. This is of course assuming you try to do it in one round. Nothing stopping you from taking multiple rounds. \$\endgroup\$
    – Imaginary
    Sep 23 '16 at 1:44
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    \$\begingroup\$ @Sebkha also page 190 mixes what you are saying with what I am saying to come to the same conclusion. If we put our heads together it would sound something more like "Using your free object interaction for the turn, you may draw your weapon as part of the same action you used to attack" which is quoted from page 190. We both agree, you just want it phrased differently. \$\endgroup\$
    – Airatome
    Sep 23 '16 at 1:46
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    \$\begingroup\$ @Imaginary No, you can't use an attack action to Doff a shield, which is why putting the shield away is marked as 'Turn 2' . \$\endgroup\$
    – Airatome
    Sep 23 '16 at 1:48

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