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My only income is ssdi, I paid $5,000 out of pocket for medical expenses, should I file and try and recoup money
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If your only income is SSDI then you do not have any tax liability so the medical expense you paid is not relevant.
If the Social Security benefits is the Only income to be reported on the tax return and there is no federal income taxes being withheld, then there is no reason or need to file a tax return.
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