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Continue to ChatWaiting on Your May SSDI Check? Here's When It'll Arrive The Social Security Administration will send your disability insurance check with one of the rounds this month. https://orbitbrain.com/blog/waiting-on-your-may-ssdi-check-heres-when-itll-arrive-the-social-security-administration-will-send-your-disability-insurance-check-with-one-of-the-rounds-this-mont/