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Email not leaving outbox

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Just over the last few days I am finding that I have to create the same email twice and send both because the first one will not leave the out box. The first email I send first goes to italic then that goes off and it shows a document icon. If I create exactly the same email in the same manner it sends perfectly fine and shows me the envelope icon. I have read the other posts like mine and followed directions from the various pages but nothing has worked.

The only change in my computer was a windows 7 update. I even tried through 365 to repair the install.

My email is IMAP/SMTP. It is an Exchange email through Shaw cable.

I followed a link in these questions and did everything it said I was to do. I'm sorry I don't remember the link and it didn't help anyway, I do remember that it was dealing mostly with 2007 and 2010 Outlook. It told me to remove the .srs file which I did and rebooted the computer. Didn't help.

On my own I have repaired the installation of 365 and rebooted the system didn't help. I repaired the email file through File-Accounts-E-mail-Email name - and repaired, the test message sent by the program did send and get received. Tested my own emails again didn't work. Rebooted the computer no change Still have to double up on the emails.

I think I have found the problem but do not know how to fix it. In every email I write when I check the "Delay Delivery" it is always check marked and is always today's date at 5:00pm. I found this before and unchecked it but it seems to be a 'stuck' choice.

This morning I repaired the installation with the on-line choice, rebooted and it still does not work.

Thanks in advance

Irene


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