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When you delete a document from iManage and subsequently Sync documents within Insolvency, the insolvency document will be marked with a red exclamation.

The document properties will show a message "Cannot find document 123456, the document may have been deleted".

Hovering over the exclamation mark will also show the error message.

If you double click on the document in Insolvency, the iManage error message will display: