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The biggest obstacle Frederick Douglass faced in learning to read was the systemic oppression and resistance from slaveholders who believed that educating enslaved people would undermine their control. His owners, particularly Sophia Auld, initially supported his learning but were pressured by her husband to cease this, illustrating the societal fear of educated slaves. Douglass overcame this challenge through determination and resourcefulness, seeking knowledge from white children and using any available materials to teach himself.

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