MSI Outlook Plugin - Log from Sent Items?

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MSI Outlook Plugin - Log from Sent Items?

We have "Sales Email Sent" and "Sales Email Received" as enabled activities in our Salesforce Sync Options.  These are working great when a sales rep uses their MSI plugin to Send and Track or when they use the Log With Marketo button for replies in their Inbox - SFDC activities are being created as expected.

Sometimes our reps forget to use the Send and Track button, so I would like them to be able to open a previously-sent message and log that with the Log With Marketo button.  When they try this, it appears to get logged in Sales Insight, but no activity is created in the SFDC record.

I don't think I'm ever going to be able to get the reps to remember to use Send and Track every time, but we really want the activity to be created either way.  Is there another option I need to enable in the Salesforce Sync Options to get this to work?

If not, is there another way for reps to easily log their previously-sent emails with both Marketo and SFDC? Thank you!
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Re: MSI Outlook Plugin - Log from Sent Items?

To make sure it gets into salesforce, you could ask them to use the Email to Salesforce feature:

Some of our reps set their Outlook to BCC salesforce on everything. Not sure I like that, but it works.

As far as Marketo goes - the send and track button is the only way. You could take away the Outlook plug-in and have them send all emails through MSI within SFDC, but I'm guessing they wouldn't like that option.