1. A method comprising: associating, via a computing device and within a memory accessible by a content monitoring device that separately monitors security of content copy and paste operations performed by the computing device, source file type information of a source file with source file content copied from the source file in response to a copy operation of the source file content from the source file by the computing device; forwarding over a network, in response to determining that a content copy tracking rule created within the memory by remote operation of the content monitoring device specifies that a content copy alert feature has been enabled within the computing device by the content monitoring device, an automated content copy tracking alert to the content monitoring device that identifies at least the source file and that documents that the copy operation of the source file content from the source file was performed using the computing device; performing an automated conversion of the source file content copied from the source file to a form compatible with a target file type of a target file based upon differences between the source file type information and target file type information of the target file in response to a paste operation; forwarding over the network, in response to the paste operation of the source file content copied from the source file and in response to determining that a content paste tracking rule created within the memory by remote operation of the content monitoring device specifies that a content paste alert feature has been enabled within the computing device by the content monitoring device, an automated content paste tracking alert to the content monitoring device that identifies at least the source file and the target file to document that the paste operation was performed using the computing device; determining that the paste operation was to an email message; and including the email message itself within the automated content paste tracking alert forwarded to the content monitoring device.