MacOS Sierra on O365 E3 won't open some attachments randomly. I can see the email has an attachment but its greyed out and I cant. I can see and open the attachment via OWA and on my phone but not on Outlook for Mac 2016. There are a few emails with the same issue and it is NOT specific to a.

October 10, 2013 Some of us simply need to always attach files in outgoing Outlook emails, especially if we deal with business emails. For example, one may need to automatically attach a business card or a brochure to all business emails. In this article we will explain how to always attach files to Outlook emails using Bells & Whistles for Outlook. What is Bells & Whistles for Outlook? As its name says, the product adds “bells and whistles” to Outlook: over 40 productivity features and tweaks designed to better your Outlook experience.

It works with all Outlook versions, including Outlook 2013 / 365. Among these features, there is the option to automatically attach files to outgoing emails. How to always attach files to Outlook emails •; • restart Outlook; • locate the Bells toolbar in Outlook and click on its Options button; • in the Options window, go to the Mail tab; • scroll down to Message Options and enable “attach the following files”; • browse and select the files that will be automatically added to emails.

When you will compose an email, the add-in will automatically attach the selected files to it. Optionally, if you want to always attach files only on emails sent to certain persons or only to new / reply / forwarded emails, you can create Bells & Whistles rules to match your requirements. The option to attach files to emails can be used in conjunction with all the other of Bells & Whistles.

Software: Microsoft Outlook 2016 (15.23) OS: OSX El Capitan version 10.11.5. Hardwre: MacBook Problem description: When I send an email with an attachment from Microsoft Outlook 2016 (15.23) to someone opening the same on an iOS device such as iPhone or iPad running the native iOS mail client, the email is received and although the email header shows a paper clip icon to indicate an attachment is present within the email, the actual email does not show an attachment! The problem does not exist if you open the same email using a desktop client such as Outlook, or Thunderbird, or indeed an Android phone running a native mail application. The problem relates to all types of attachments, PDF, Word,.jpg etc.

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Summary Troubleshooting. Outlook 2016 (15.23) to native mail client on iOS - Paperclip shows but no attachment Outlook 2016 (15.23) to desktop clients (Outlool, Thunderbird) - OK - Attachments show Outlook 2016 (15.23) to native mail client on Android - OK (attachments show as normal) Outlook 2016 (15.23) to Outlook email client app on iOS - OK (attachments show as normal) Native MAC Mail client 9.3 (3124) to native mail client on iOS - OK (attachments show as normal) The problem specifically realtes to sending email from Outlook 2016 (15.23) to native mac app on iOS.