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If the Outbox emails are NOT marked with bold (as you wrote), then they will never get emailed by Outlook. Normally, an Outbox email if marked with the regular font style (not bold) if you manually clicked on each Outbox message and previewed (or opened) it. This is just how Outlook works and this behaviour is not related to Easy Mail Merge.
The only solution is to erase the Outbox emails and create them again.
On the other hand, when schedulling the outgoing emails, please make sure that the specified time period is smaller or equal to the Outlook send/receive settings. So if you choose to send emails every 100 seconds, make sure that Outlook is also configured to automatically send/receive emails every 100 seconds or sooner.
Also, if you are using Outlook with Exchange, please make sure Outlook is always connected/online with the Exchange server.
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