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If you're using a web browser such as Internet Explorer, Chrome, Firefox or Edge to access eduMail at www.edumail.vic.gov.au instead of Outlook or Mail and cannot add attachments, make sure your Microsoft Silverlight is up to date.
Microsoft Silverlight can be thought of at something like Java or Flash in that it is a browser plug-in that needs to be kept up-to-date.
Silverlight should automatically update but sometimes does not do so successfully.
Update MS Silverlight manually from here > Microsoft Silverlight <.
Quit your browser. Reopen edumail and retry attachments.
For best results, use Internet Explorer, or, on a Mac, try Safari.
**Please note that as of April 2018, Google Chrome have stopped supporting this plugin altogether and so will no longer allow the "attachments" dialog on eduMail.
The only options available are to use Internet Explorer (or possibly Safari on aMac) or a proper Mail Application such as Mail.app(on Mac) or Outlook(on Mac or PC)