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Michael M 
My research is showing that it is partially possible to do this using standard functionality. There have been discussions around this. See the latest comment from Salesforce on this Idea
"Parameters that accompany the option to "Send through Salesforce" (in a user "My Email Settings" page) apply when sending List Emails from Lightning (an email is issued when switching mailboxes to confirm validity). That's one way to change the From and Reply-To. While you can modify the sender display name in these records, there is no option to configure the From address in a List Email such that it dynamically changes to equal the record owner's email address for the lead/contact currently being processed. I can visualize the flows you've described for this idea though, and when it proves valuable.
About the dropdown that appears in 1:1 emails: the composer's From field shows the user's current email address, as well as org-wide email addresses made available to the user in that org. Users with an Inbox license may also connect multiple email accounts to their Salesforce profile; all of these addresses will appear in the dropdown when composing 1:1 emails. That does not cover all of the scenarios mentioned on this idea's comments, but may be helpful to some of you"
If this is not helping you, as a workaround, I suggest going with a customized approach - Querying for OrgWideEmailAddress as shown below and sending the email using Messaging.MassEmailMessage
for(OrgWideEmailAddress owa : [select id, Address<font color="#FF0000">, DisplayName</font> from OrgWideEmailAddress]) {If you find this information helpful, please mark this answer as Best. It may help others in the community. Thank You!
Anudeep
All Answers
My research is showing that it is partially possible to do this using standard functionality. There have been discussions around this. See the latest comment from Salesforce on this Idea
"Parameters that accompany the option to "Send through Salesforce" (in a user "My Email Settings" page) apply when sending List Emails from Lightning (an email is issued when switching mailboxes to confirm validity). That's one way to change the From and Reply-To. While you can modify the sender display name in these records, there is no option to configure the From address in a List Email such that it dynamically changes to equal the record owner's email address for the lead/contact currently being processed. I can visualize the flows you've described for this idea though, and when it proves valuable.
About the dropdown that appears in 1:1 emails: the composer's From field shows the user's current email address, as well as org-wide email addresses made available to the user in that org. Users with an Inbox license may also connect multiple email accounts to their Salesforce profile; all of these addresses will appear in the dropdown when composing 1:1 emails. That does not cover all of the scenarios mentioned on this idea's comments, but may be helpful to some of you"
If this is not helping you, as a workaround, I suggest going with a customized approach - Querying for OrgWideEmailAddress as shown below and sending the email using Messaging.MassEmailMessage
for(OrgWideEmailAddress owa : [select id, Address<font color="#FF0000">, DisplayName</font> from OrgWideEmailAddress]) {If you find this information helpful, please mark this answer as Best. It may help others in the community. Thank You!
Anudeep