On Mon, 2020-09-28 at 19:42 -0500, J.B. Nicholson wrote:
> Is there a way to change this either to let me set headers on
> outgoing emails as a rule or,

        Hi,
I do not see anything else but the "Pipe To Program", but that feels
like an overhead for such thing like changing the Reply-To.

> failing that, to let me use address book lookups and help me fill in
> the Reply-To: header based on those address book lookups?

The To/CC/Bcc auto-completes with recipients, not with the senders.
This kind of lookup won't help in the Reply-To.

One option could be to create a send-only account with prefilled
Reply-To and setup Evolution to use that account for certain mail
folders/recipients (through the Send Account Override).
        Bye,
        Milan

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