ICloud Email Issue: Messages sent to same account

Issue:
When sending an email from my (personal-email)@me.com to the same account, with an attachment, email doesn't show up on any devices, even Apple mobile devices.
Troubleshooting Attempts:
- Sending emails on iMac machine with attachments from (personal-email)@me.com to (personal-email)@me.com ISSUE PERSISTS
- Sending emails on MacPro machine with attachments from (personal-email)@me.com to (personal-email)@me.com ISSUE PERSISTS
- Sending emails on Mabook Pro machine with attachments from (personal-email)@me.com to (personal-email)@me.com ISSUE PERSISTS
- Sending emails on iPhone 4 device with attachments from (personal-email)@me.com to (personal-email)@me.com NO ISSUE (All Devices Recieve)
- Sending emails on iPad 2 device with attachments from (personal-email)@me.com to (personal-email)@me.com NO ISSUE (All Devices Recieve)
- Sending emails on iCloud.com with attachments from (personal-email)@me.com to (personal-email)@me.com ISSUE PERSISTS
- Re-setup (personal-email)@me.com account on all devices ISSUE PERSISTS
- Turned Push on/off on all devices ISSUE PERSISTS
Additional Observations:
- All devices are able to send emails without attachments to the same email without any issue.
- When an attachment is added, the message can only be found in the 'Sent Messages' folder on each device (Besides those sent from my mobile platforms)
- All devices are able to send emails without attachments to the same email without any issue.
Devices and Versions (In order of Frequency of Use):
iMac Quad-Core i7 - OS X Lion (Up-to-Date)
MacPro 12-Core - OS X Lion (Up-to-Date)
Macbook Pro 15" i7 - OS X Lion (Up-to-Date)
iPhone 4 - iOS 5.1.1 (Up-to-Date)
iPad 2 - iOS 5.1.1 (Up-to-Date)
Possible Issue Defining Variables:
(Note: All other devices where up-to-date before the following occured
- I have recently moved my mobile me account to iCloud (On the last day possible to do so)
- After moving to iCloud, I immidiately updated my Snow Leopard iMac to the most up to date OS X Lion.
Hopefully this details out all the things you may need to help me out. I can't go into an Apple story due to the amount of different devices I have.
Be advised, this issue isn't loyalty deterring, as much as it is annoying. This used to work before moving to iCloud, if it can be fixed, that would be awesome.
Thanks,
VV

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nicholasfromchillicothe wrote:
No joy - I am still getting a warning sign popping up saying "Cannot send message using the server iCloud (iCloud)", along with a list of alternate SMTP servers to try, based on the other accounts my Mail program is connected to.
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