Solution
While my situation was quite unique, I thought I'd share this for anyone who may be having this same issue. My client was using a shared server. That shared server uses shared proxies for email. Some of the IPs on those proxies were being blocked. I reached out to the hosting company and had them remove the blocked IPs as a short-term fix and will likely end up moving to an email service or a dedicated server to prevent this issue from coming right back.
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