I have a rule set up in Outlook 2010 at work (we use Exchange Server) and it is supposed to forward any emails from my family to my gmail account. It does sometimes and not others. If I run the rule manually the results are the same. Currently I have 3 emails in my Outlook inbox and it will forward one of the 3. The only thing I can think of is that the one it forwarded is from one sender and the rest are from multiple senders - most of the people who sent these are in my rule so why does it only work when it wants to? I know the rule only works on unread emails but I can only mark some emails as unread - some will not allow me to change their status from 'Read' to 'Unread'. How annoying. I am putting this in the "Exchange Server" category since there is no Outlook category. Thanks

A message can have multiple recipients, but it can only have one sender, so I'm not 100% sure of what your two unforwardable messages might look like. That being said, are you using contacts for your family members, or have you put their SMTP addresses in the rule? I've seen where a messaging system makes minor changes to an outbound message or a user has a slightly different email address, and a rule fails due to this.

I did just noticed that I got some of these emails as a CC not the original recipient - would that make the rule not work? Also noticed that when it does forward the emails they often don't arrive in my gmail account. When I look at them in the Sent folder of Outlook my gmail address is shown as 'cduwel@gmail.com' (including the single quotes. Only emails forwarded with the rule have the single quotes and although they sometimes arrive mostly they don't. In the rule I picked the senders from the contacts list but I had to type in my gmail address - I don't know why it can't find it sine if I make a new email in Outlook to myself it pops the gmail address as soon as I type a few characters.

If your rule has the "If the message is sent from" clause and has no "and I am on the To: line" clause, it should work. However, if you are using some of the default rules, they have the second clause built-in. See if you can change the rule so it has the "and I am on the To: or Cc: line" clause, and this should fix your problem.