In Lightning Experience, the email attachment icon disappears after an email with an attachment is sent from the Salesforce Email Action. The attachment is successfully sent to the recipient, but the attachment icon does not display in the Activity Timeline UI.
This issue only occurs when all three of the following conditions are true:
This behavior is working by design. When Einstein Activity Capture (EAC) is enabled for a user, EAC takes over the email display functionality in the Activity Timeline (referred to as "Past Activity email crawling"). EAC crawls emails from Salesforce's server and currently supports emails only — file attachments are sent successfully but are not shown in the Activity Timeline UI because EAC does not currently support displaying file attachments in this view.
The email is delivered successfully to the recipient with the attachment. The limitation is in the UI display within Salesforce, not in the delivery of the file.
To restore the attachment icon display, deselect EAC (Einstein Activity Capture) from the App Permissions on the assigned user's Inbox Permission Set. This removes EAC's control over the email display and restores the default attachment icon behavior.
A related product Idea requesting this functionality has been submitted and can be viewed here.
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