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One of the users that I support has been having problems with his Outlook and being able to use the Document cloud Add-in that comes with the Acrobat installation. At this KB link, it shows the behaviour that he wants https://helpx.adobe.com/uk/acrobat/using/adobe-document-cloud-for-outlook.html however, this button does not appear when composing new messages. When he attaches PDFs normally, he also doesn't get the prompt to change to using a link.
He gets the Acrobat tab that allows attaching as PDF and the settings button, just not the ability to send as a link directly in Outlook.
I have tried reinstalling Acrobat, Office, removing and re-adding the add-in directly within Outlook from the options. Always send files as a link is ticked in Acrobat preferences.
He is using Outlook 365 semi annual channel.
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I have the same issue. A workaround I found: if I 'Pop Out' the email message so it appears in its own window (not in the compose pane in Outlook) I then see a different menu option which works as expected:
Hope this helps while we wait for an Adobe fix here...