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Need some help with email

We use O365 as our email server. One of my sales reps reported the following behavior and i have confirmed it, and am now looking for solutions.

She sent a quote to a customer directly from Netsuite and it bounced as undeliverable with fairly generic error messages. She then saved the quote as a pdf and sent it as an attachment from outlook and the customer received it.

I am guessing the issue has something to do with SPF or DKIM approvals. I have all my DNS records setup properly according to Netsuite, but my suspicion is there is a conflict that is causing receiving email servers to reject some emails from inside netsuite.

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