I don't know "why", but I did figure out somethign this morning. My main email account is a POP3 connection to my mail server using Outlook. My email signture contains a graphic. When I open an email I sent on my iPad, the image is stripped out (although there is a suspicious WinMail.dat that makes me think something is reformatting the email). I fiddled with my email signature where the image was pasted in, and inserted as an image using various formats (GIF, PNG, TIF, JPG), all the same results. My outlook email format is HTML.
Then I tried the same thing from my other corporate email account that is attached do an Exchange Server... and that works. My signature on my Exchange mailbox has a copy/pasted image in it, HTML as the format and the image always shows up on the ipad. No Winmail.dat
So...here is the crazy part. I emailed myself from my POP3 mailbox to my Exchange mailbox...when I opened that email from my Exchange mailbox on the Ipad, the image was there.
So... does the iPad strip images that originate from a POP3 connection, or does the POP3 server change the format of the email such that the iPad no longer displays the image inline?
I'd be curious to know if all the others having trouble with images in their Outlook signature are also using a POP3 connection from Outlook...