Outbox - Multiple Emails need to be manually opened?

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FC-16

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Outlook 2010 32 bit
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IMAP
This 'new' question relates to a previous question I posted on here titled: "Tumblr - Drag & Drop files (pictures) into Outlook". Maybe to understand 'this' question you might need to lookup and read that question/thread.

So .. I open up the 'Pictures' Folder on my PC and select all the pictures I want. I drag/drop them directly into a Folder within Outlook. I then run a rule which simply moves all the items dropped into that Outlook Folder to the Outbox

As a way of an example, look at the screenshot I have taken and you'll see 20 items in the Outbox. The first 10 messages are the ones the rule moved there--they are 'bold' in color, they are 'italic' and have a yellow envelope. The other 10 messages have an opened mail icon, are not bold or italic.

Why do I have to manually open all 10 emails and click send 10 times for them to turn from their 'bold', italic and yellow envelope so they now all appear with an opened icon? Why doesn't the rule do this?

screenshot.JPG
 
On second thought... i think i misread the question last night - they are unsent messages, so you don't want them read, you want them unread.

Do they send ok if you don't look in the outbox? (They did here.) Some addins will mark messages read if you look in the outbox.
 
Just tried a test on 5 messages. When the rule ran it put 5 messages into the Outbox which had an opened mail icon, were not bold or italic (look at the screenshot in my original/first question; look at the top 10 messages, the ones with opened mail icon) and yes, they did send ... HOWEVER, when those messages were sent to my Tumblr publishing address the pictures were not published.

The 2nd time I ran a test it worked.

So this is 'The Question' ...

This time I pressed CTRL+A to select all messages in the Outbox. Right click the mouse and select 'Open' from the context pop-up window. This opens all 5 messages (if I had 50 messages in there then 50 individual messages would open .. and so on). I then click 'Send' on each of the 5 emails and now those 5 emails have changed from an opened mail icon, are not bold or italic TO 'bold' in color, 'italic' and have a yellow closed envelope ... then I click my Send All shortcut and all messages are sent AND all pictures appear on my Tumblr Blog.

So the only way for me to do what I want to is manually open all messages in the Outbox and click 'send' on them all for this to work. Outlook isn't doing something right automatically here ... hmmm
 
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