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I'm using Google Chrome 43 and I can't add attachments in a new message in Outlook Web Access (OWA). While looking into it, I discovered that this has been an issue since the removal of 'showModalDialog' since Chrome 37. But apparently a workaround is to install Silverlight. But I have version 5.1.40416.0 of Silverlight and it still doesn't work. I think I'm using Outlook OWA 2010. Is there any way to fix this? Attachments work fine if I use Internet Explorer 11.

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OWA, designed by Microsoft, is best supported by their browser, Internet Explorer just as Google products, like Hangouts, work best in Chrome.

In Microsoft's own documentation, they say that OWA works best on Windows 8 clients, running IE 10 or 11. Support for Google Chrome is rated as "Good" or "Best" depending on the Exchange backend server hosting OWA. If the server is running Windows Server 2008 R2, for example, Chrome support is rated as only "Good".

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When you click the paperclip icon to add an attachment in Outlook Web App (OWA), your browser should launch a file window so you can choose a file to add. If nothing happens when you click the attachment icon, this could be because:

  • You are using Google Chrome version 37 or later. In version 37 of their Chrome web browser, Google introduced a change which effectively disabled OWA's attachments button.

    You can work around the problem by using OWA light (click on More login options and then the Use OWA Light option before logging in) which uses a different system for attachments which works on Chrome 37+ as well as browsers without the Silverlight plugin.

    On Windows PCs, you can also try upgrading Silverlight as this sometimes re-enables the attachment button.

    Alternatively, you could use OWA with an alternative web browser, such as Firefox.

  • Other browser, with browser plugin name "Silverlight". Other web browsers that use a plugin called Silverlight to handle attachments but if the plugin malfunctions for any reason, attachments will cease to work.

    In this case, the quickest solution is usually to install or upgrade Silverlight.

source: http://www.sussex.ac.uk/its/help/faq?faqid=2697

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