Hi @Tim Martin ,
Welcome to the Microsoft Q&A platform!
First of all, please check if the outlook client is set to delay sending.
The fact that it can send normally means that there is no problem with the connection. Consider force flushing the DNS cache or check the protocol logs.
Clear-DnsServerCache -Force
If you are still having problems, please provide details. For example, whether the problem is with a single user or multiple users, how often it occurs, and whether there are any anti-virus settings, including protocol encryption.
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