Documentation for JIRA 6.3 EAP developer (EAP) releases only. Not using this? See below:
(JIRA 6.2.x documentation | JIRA OnDemand documentation | earlier versions of JIRA)

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To prompt for an attachment on the Create Issue page, go to the relevant Field Configuration page (eg. Administration -> Issue Fields -> Field Configurations -> Default Field Configuration), and unhide the 'Attachment' field.

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  1. One more check point before this.
    Check attachments setting is ON.

    Refer to this. (smile)
    Luke