How do you send a file through iMessages

On my mac I can drag a file over to imessages, I can even download it on another id on the mac. I have tried to send the same file to my iphone and ipad and nada.
Yet, I have no problem with pictures.
How do you send files through iMessage to your ipad?

Yes, that works from mac to mac. That is a wonderful feature.
I did find Apple's list of supported files and it is not complete. It did not list PDF as a supported file so I suspect there are others. I am afraid that epub and some others that would make life easier are not supported at this time. I did find reference to where the file i on the ipad but you have to jailbreak your iphone and/or ipad to do that and I am not interested in doing that.

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                err_conv_not_possible    = 4
                err_bad_destdevice       = 5
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                err_temseerror           = 8
                err_btcjob_open_failed   = 9
                err_btcjob_submit_failed = 10
                err_btcjob_close_failed  = 11
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                                          gd_reciever.
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                                              p_filename
                                              p_attdescription
                                              p_sender_address
                                              p_sender_addres_type
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                                              p_reciever.
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            ld_reciever TYPE sy-subrc,
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            ld_attdescription TYPE  so_obj_nam ,
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      w_doc_data-obj_name  = 'SAPRPT'.
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      REFRESH t_packing_list.
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      t_packing_list-head_num = 0.
      t_packing_list-body_start = 1.
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                too_many_receivers         = 1
                document_not_sent          = 2
                document_type_not_exist    = 3
                operation_no_authorization = 4
                parameter_error            = 5
                x_error                    = 6
                enqueue_error              = 7
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      ld_error = sy-subrc.
    * Populate zreceiver return code
      LOOP AT t_receivers.
        ld_receiver = t_receivers-retrn_code.
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