Here's an issue my company's IT folks haven't been able to crack. Outlook 2010 is networked for the large company.
I have been unsuccessful in adding a portrait to my email messages, but have had an anomaly occur in the course of attempting it.
I added a photo to my email profile through the corporate employee portal, where the profiles are editable. The photo shows up perfectly in my Outlook contact listing for myself, including on my e-business card in the application as accessed on my local machine, i.e., when I open my own contact listing in Outlook. However, when I create and send messages, it does not appear. I do see others' portraits in emails I receive.

Here's where it gets weird: In my office account's contact listing for myself on my local machine, I had earlier included a personal email address, a Verizon domain account, as Email 2. This caused something fascinating: I happened to send an email message from home to work, a reminder for something. That email appeared in my work inbox with the portrait, which is not in my home Outlook! When I removed the Email 2 address from my work Outlook, this anomaly disappeared, though still no portrait in my work-originating emails. When I recreated the Email2 with the personal address, the same behavior reoccurred: messages sent to me from my home account to work showed the portrait. It does not show if I sent it to anyone else.
I still cannot get the portrait to show up in my work emails. Any ideas?

The problem apparently had to do with the size of the image; it was small but still too large. Evidently, Outlook needs the image to be near the size it will appear in the message header. There must be a limit somewhere.