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Undeliverable Office 365 email error

Intermittently, I am unable to get an email through to my client. Worked fine for several months and then this happens...

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GD support shows email being sent and recd yet the msg doesn't go through. Recipient's spam filter also shows my address as clean so not blocking. Will eventually resolve, msgs go through, and then returns. Other msgs to same domain go through fine except one or two individuals. "System Administrator" appears to be my Outlook 365.

 

TIA