Issue
When using the Salesforce for Outlook (SFO) Side Panel, clicking the envelope icon to add an email to a Salesforce record succeeds. However, when selecting one or more attachments to add to the record, the operation fails with the following error:
We couldn't add this item. Please try adding this item again.
The Salesforce for Outlook log file records an INVALID_SESSION_ID error at the time of the failure. This error indicates that the Salesforce session has expired or has been invalidated due to an IP address change during the session.
The specific log entries show an AssociationError with status error, error type Unauthorized, and an INVALID_SESSION_ID session code — meaning Salesforce rejected the session token because the IP address from which the session originated has changed.
This issue is caused by a Salesforce org-level security setting — Lock sessions to the IP address from which they originated — and is not a defect in Salesforce for Outlook itself.
Root Cause
The Salesforce "Lock sessions to the IP address from which they originated" setting invalidates the session token when the user's IP address changes mid-session (for example, due to a VPN reconnect, network switch, or DHCP lease renewal). When SFO's side panel attempts to attach files, it uses the same session token, which has been invalidated — causing the "couldn't add this item" error.
Resolution: Disable Session IP Locking
A Salesforce Administrator must log in to the org and disable this setting.
After Disabling the Setting
Restart Salesforce for Outlook to apply the change:
Refer to the article Modify Session Security Settings for more information.
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