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Robin L have the same problem so I am interested in any response as well
I have found that some unopened messages will not delete until I open them and other opened messages will not delete until later on
I believe the problem is in the live mail program as it has appeared since win 10 was installed then deleted along with unable to fix live calendar keeps coming up in the notifications
Any teck savvy experts that can give a response I would also appreciate
I do not like Outlook, it is not good, I choose to use IncrediMail, I think it is good, you can try this, reset the details, and it will not appear that problem. You can get it here: http://softsbay.com/download/IncrediMail-3418.html
Generally if the phone is giving a "cannot send" or "message failed" error message then there is something wrong with the "switch" In order to fix this you need to contact your providers tech support and they should be able to fix the issue...
You can also try sending the picture to your own number... sometimes that will help push it through the switch...
Also make sure that you are using the area code of the numbers that you are sending it to...
Alltel for example, will not let the message go through if the area code is not inserted