I originally asked this at
http://answers.microsoft.com/en-us/office/forum/office_2010-outlook/attachments-not-visible-when-in-html-mode-outlook/c50add8c-15fa-4c43-a2b6-58c78e9ec542
and was referred to here. This has to solely do with a couple clients running on a 2010 exchange server. I do not have access to the server but as far as message formatting nothing has been set.
I have a couple users (out of about 500) that have attachments missing from Outlook. For example they send an email with an attached PDF to a couple users and they also cc themselves on it. When the people with the issue receive the email several things may happen.
1. They receive the email as normal with no issue.
2. They receive the email with the paperclip icon but upon opening the attachment is not listed under the header like normal.
3. They receive the email without the paperclip icon and the attachment is not under the header.
In all three cases the email file size is appropriate. I have found a workaround for this but have not figured out the cause or a permanent solution.
Under trust center settings I set them to receive all messages in plain text. After doing so the error does not occur and messages that were previously missing attachments now have it under the header as expected. Also just to note OWA does show everything the way it should be. Now if I open a message in plain text with the attachment and click the part that allows me to now open it in HTML the attachment disappears. I have saved the message to my computer (and I have not experienced this issue) and the same thing will occur with the attachment missing. I have checked their outbound setting which are set to convert outgoing to HTML.
It seems upon examining the emails code (not done by me) that the emails where the attachment is missing is attaching the PDF as inline even though it was attached as a regular attachment using the attach file button. The work around would be to have everything as plain text (send and receive) but I'm looking for a solution.