Outlook 2011 14.2.3 on OS X 10.7.4.
1 Account, Exchange 2010 on premise.
iPhone iOS 5.1.1.
I'm unable to send emails with photo attachments from Outlook to iOS devices using either the Attach button or dragging a photo into the header area as an attachment. Jpg, PNG, don't work.. saving a photo from Photoshop CS5 as a Photoshop PDF does not work
either. However, using the OSX Print->PDF dialog to save as a PDF works just fine in iOS.
However: if I drag the photo into the body of the message (html) it will send it just fine. The downside is that it embeds the photo at full size, making it very unwieldy.
The attachment is broken whether sending *to* my exchange account or my gmail account.. both of which are on my iPhone, yet if I send the same photo using OWA or Gmail it works fine to the either iPhone account.
Full scenario:
Email will show in the Inbox as having an attachment.
Click on the email and attachment shows as "mime-attachment 400kb" icon.
Click on icon.
Here the scenario diverges:
Sometimes (but only on the first attempt) the icon is clickable and will start to download the attachment and display it successfully. If this happens, and afterwards you click back to the Inbox, then back into the email, the photo is gone and has been
replaced by an unclickable "mime-attachment 400kb" icon again.
The majority of the time the icon is unclickable. It zooms in a little and zooms back out again.
However, if you Forward the email, and "Include" the attachment.. it will show the photo correctly in the to-be-Forwarded email, even when it did not successfully show it before.
Troubleshooting so far:
I have tried many different images, both from my own Library as well as just random images from the internet for testing (I thought it might be a corrupted image, or even an unsupported jpg standard from my scanner or something).
Aside from trying all of the above I have also rebuilt my Identity (just once, successfully), and rebooted the Mac and Outlook.
Ran software update on both the Mac and Microsoft, and made sure I was fully up to date.
This is happening on two different macs sending to 3 different iPhones. I have one dev iPhone running iOS 6 Beta 3 and it seems to work more often than iOS 5, but still doesn't work all the time.
Any ideas?
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