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Will I get the feat bonus if I am using both hands to wield a two-handed weapon and having the Winged Shield float near me?

The feat:

Shield Specialization

Benefit: You gain a +1 feat bonus to AC and Reflex when using a shield with which you are proficient.

And the item:

Winged Shield

Property: You do not need to use your shield hand to gain the shield’s bonus to AC and Reflex; it floats about within your reach as if you wielded it. You can use your shield hand to hold another item, climb, wield a weapon, make attacks and so on. If you have a free hand, you may count as wielding a shield as a free action. Attempts to take away the shield are resolved as if you wielded it normally.

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Yes.

The key part is in the description of the shield:

Property: You do not need to use your shield hand to gain the shield’s bonus to AC and Reflex; it floats about within your reach as if you wielded it.

So the floating counts as wielding the shield, so the feat bonuses will apply also.

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  • \$\begingroup\$ But it also says "If you have a free hand, you may count as wielding a shield as a free action." and in this case, the character has no free hand. \$\endgroup\$ – Petr Hudeček Mar 28 '15 at 17:31
  • \$\begingroup\$ Then it's not a free action to wield. Has no bearing on the bonuses. The shield counts as being wielded. That's all that is necessary for the feat bonuses. \$\endgroup\$ – JohnP Mar 28 '15 at 17:36
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    \$\begingroup\$ It sounds contradictory to me; they first say "as if you wielded it", implying that you are always wielding it, but then they state "you can count as wielding it as a free action", implying that you aren't always wielding it. \$\endgroup\$ – firedraco Mar 28 '15 at 18:49
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    \$\begingroup\$ @firedraco - You aren't always wielding a shield even if it isn't floating around you. If you have it stowed, wielding it is a free action. Then the bonuses kick in again. \$\endgroup\$ – JohnP Mar 29 '15 at 14:45

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