Forum Discussion
benlewis12
Nov 25, 2025Copper Contributor
Strange Issue with Outlook Classic Encrypted Emails
We have the option to Encrypt outgoing sensitive emails manually but also have DLP rules set up to catch PII if a user forgets to manually encrypt. Everything was working up until we applied an Offi...
Nov 27, 2025
Hi Ben, did you try creating a new Outlook profile? I would do that and test it after you let it set up for 15 min or so. If it fails, give it more time. Keep the old profile until you validate this new one works to preserve settings and data. A new profile gives it a fresh connection to the server.