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I have a list with a "New Item" form that has the built-in "Attach File" button at the top. If I want to upload I file then I can click on that button and I am taken to a page where I can choose the file using Windows Explorer browsing. However, this only allows me to attach one file at a time. If I would like to attach multiple files then I have to click on the "Attach File" button, choose another file, and repeat this process for every other file that I have.

Obviously it would have been better to just allow the user to attach all their files with one fell swoop of the Windows Explorer browser but the SharePoint development team did not include that. Does any one know of an alternative solution using perhaps a custom column with a file selector allowing multi-file selection?

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The telerik silverlight upload control in 2010 should do it, or you can create your own.

There are a few tutorial on how to make one in silverlight floating around the web.

The basic answer is SilverLight, the OOTB one relies on ActiveX from office 2010.

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A little late, but you may also use the Datasheet view in SharePoint, right-click on the attachment cell and select Edit Attachments. From there, you can click on Add and select multiple files to load to the SharePoint List Item.

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Really late, but if I came accross this issue, someone else might as well.

I had a similar problem and came up with a way for the users to browse and attach to the list all on one form.

All OOTB btw.

I created a new "Edit Form" in Designer (making sure not to set it to default); set it up including the code below; then used a quick action button to call it to my site banner. I was able to place in the same spot where the "Attach File" button was in the "Actions" section using "Ribbon.ListItem.Actions.AttachFile" as the Ribbon Location.

Anyway, hope this helps anyone still struggling with SharePoint 2010's multiple attachment upload drawbacks/issues.

    <tr>
        <td>
            <table border="0" cellspacing="0" width="100%">
                <tr id="idAttachmentsRow">
                    <td nowrap="true" valign="top" class="ms-formlabel" width="20%">
                        <SharePoint:FieldLabel ControlMode="Edit" FieldName="Attachments" runat="server"/>
                    </td>
                    <td valign="top" class="ms-formbody" width="80%" id="attachmentsOnClient">
                    <INPUT name="Button1" type="button" value="Attach" onclick='OkAttach()' style="width: 101px" />
                    <br /><br /><SharePoint:FormField runat="server" id="AttachmentsField" ControlMode="Edit" FieldName="Attachments" __designer:bind="{ddwrt:DataBind('u','AttachmentsField','Value','ValueChanged','ID',ddwrt:EscapeDelims(string(@ID)),'@Attachments')}" Version="4" />
                        <INPUT name="fileupload0" tabindex="1" title="Name" class="ms-longfileinput" id="FileUpload1" type="file" size="51" />
                        <script> var elm = document.getElementById(&quot;idAttachmentsTable&quot;);
                               if (elm == null || elm.rows.length == 0) document.getElementById(&quot;idAttachmentsRow&quot;).style.display=&apos;none&apos;;
                            </script>   
                    </td>
                    <td colspan="2" class="ms-vb">
                            <span ddwrt:amkeyfield="ID" ddwrt:amkeyvalue="ddwrt:EscapeDelims(string(@ID))" ddwrt:ammode="view" xmlns:ddwrt="http://schemas.microsoft.com/WebParts/v2/DataView/runtime"></span>
                    </td></tr></table>
        </td>
    </tr>

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