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Ewan
Hi,
For your scenario, I agree, separate ad-hoc encryption is required (e.g. external addresses).
The systems I administer use Microsoft DLP which uses our existing Office 365 cloud infrastructure. You can set up certain trigger words, sensitive information categories, external address activation, encrypt only if a specific sender, manual activation etc.
There’s a good video which explains Microsoft’s solution but it also explains the general principles of all vendors’ DLP solutions in case you’re not familiar.
I don’t know what part of the world you’re in, but if you don’t want Microsoft, then Zix are another huge provider in the USA as are Proofpoint.