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I understand that during his initial training with Urahara something occurred that gave him (or awoke in him)

hollow powers,

but hardly anything is said on the matter. And how come nothing like this never happened before, to the point of Urahara trying to make it possible. For Ichigo just happened?

And how does this play into

Aizen's initial plan. Did he influence this event too?

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While SingerOfTheFall's answer seems correct, it isn't. When you find out about Xcution (organization of Fullbringers) you learn that they have been in an incident with a Hollow as a child. As in, a Hollow killed their parents when they were young.

In Ichigo's case, his mother was attacked by a Hollow, thereby giving Ichigo Hollow powers.

From the wiki on how Fullbringers are made,

However, they differ in that they each have a parent who survived a Hollow attack before they were born. As a result, traces of the Hollows’ power remained in their mothers’ bodies, which were then passed onto them at the moment of their birth.

However, it probably didn't awaken until he was pushed to the edge by "training" with Urahara due to the Shinigami powers overwhelming the Hollow powers. His situation is similar to what happened in the manga recently (major spoiler):

Ichigo got Quincy powers by releasing a massive amount of spiritual energy. He got Quincy powers because his mother was a Quincy.

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  • Wait, how exactly does that happen? How does Ichigo gained Hollow powers from the Hollow?
    – rae1
    Dec 22, 2012 at 2:35
  • @rae1n I've updated the answer and showed how fullbringers came into existence.
    – Blue
    Dec 22, 2012 at 10:50
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It's pretty simple. When Urahara starts training him, in the end of chapter 60,

Tessai breaks Ichigo's Chain of Fate. Urahara explains that the corruption of the chain has already begun, and when it reaches Ichigo's chest, he will become a hollow. The only way to stop that would be to regain his Shinigami powers. Then they throw Ichigo into the hole, and seal him with bakudou 99.

In the end of chapter 62,

the chain corruption gets to Ichigo's chest, and he starts transforming into a Hollow - you can clearly see his mask appearing (though Urahara comments that the mask forming before body indicates that Ichigo is resisting the transformation). However, Zangetsu helps Ichigo to stop the transformation in the middle and regain his Shinigami powers.

So yes, the reason is simply that

he was already half-transformed into a Hollow when he gained his Shinigami powers back and stopped the transformation.

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  • +1 Plain and concise. However, how come Ichigo's the only to gain Hollowfication like this?
    – rae1
    Dec 22, 2012 at 2:32

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