First, the text:

I bolded the emphasis for the question. Now, I don't see any stipulations or restrictions regarding a number of times this can occur per turn, other than it cannot happen when the agent is MC'd. So what qualifies? I know that free actions, like perplex, trigger it. What about if you say, move. That's an action, raise your defense by 1. Then later in the same turn, you perplex up your defense. Perplex is an action, and since you were given an action..? Follow?

What about characters like Doppleganger, who can theoretically act twice in a turn? He takes an action to flurry, raising his attack. Then someone takes a token for his Mindless Pawn power, granting him another action. Can he raise attack again, or damage, etc?

I understand that ICWO was printed before any the shenanigans Special Powers can pull off, but still, I can't be the only person to say "Wait, what if you take more than one action a turn?"

This has been corrected to be an action that causes the placement of a token

Check the players' guide

Edit:
IN CONTACT WITH ORACLE
 If Oracle is removed from the battlefield and placed on the
In Contact With Oracle feat card her team ability cannot be
copied by figures with wildcard team abilities. It may be
selected by a wild card under the effect of the Loyalty
BFC.
 Free actions may not be used to give an Agent the +1 to its
combat values.
 When an Agent already has a power showing on its dial
that Oracle has, it may not be granted that same power
from Oracle.
 Oracle grants causes the Agent to possess the power that is
showing on her dial. The power that the Agent has been
granted can be countered. If the Agent is KOd, the effects
of the power are lost.
 The power action given to an Agent to use one of Oracle’s
powers is given for that effect only. You cannot assign a
power action for, say, Charge, and click Oracle’s dial and
then use Charge.
 Only one Oracle figure may be placed on the card.

While the text of In With Contact With Oracle doesn't reflect it, the feat has long been clarified to only activate when the character using it is given a non-free action. (So free actions will not activate it.) Because of this, it can only trigger once per turn. (Since a character can only be given one non-free action per turn.)

From the Player's Guide:
Technically the change was to disallow free actions from activating the feat. A free action that placed a token on the character would not activate ICwO.

Thank you. I should have checked there first.