Outlook 2010 iCloud Add-In causes emails not to send

I just started using iCloud to migrate my Outlook 2010 contacts and calendar to iCloud and then to my iPhone 5s.
There's an intermittent problem (although I can now make it happen, so not so intermittent anymore) where my emails will not send unless I disable the iCloud Add-In. They appear as Drafts (not italicized in my Outbox) and will not send until I disable the iCloud Add-In, and go back into them and click 'Send' again.
Disabling my iCloud Add-In means that my Contacts and Calendar do not update to iCloud (and thus not to my phone either), so I have to be careful to remember to enable the iCloud Add-In immediately after getting my emails sent.
Does anyone have this problem and/or a fix for it?

Thanks all.
Was checking to see if the issue Samorren has discovered in the following post might have been in play for you:
iTunes 11.1.4.62 freezes while syncing with Outlook
(Similar issues can hit iTunes and the iCloud machinery, because they both use files from Apple Application Support ... hence the quick check of your situation over here.)

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Outlook 2010 iCloud Add In

Ever since the last iCloud Control Panel update, I can't sync calendars anymore.
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I know this is iCloud because I have unchecked all but the iCloud Add In and had the problem. When I uncheck the iCloud Add in, everything sends fine.
Does anyone else have this problem, and has anyone found a solution?

guys I solved the issue.
- you need to open Outlook as an Administrator
- go to "File" then "Options"
- "Add-ins" and "Com Add-ins"
- Locate "iCloud Outlook Add-in"
- Highlight it and note the exact location of the .dll file which is shown in the bar below
- whilst the Add-in is still highlighted select "Remove".
- select "Add" and go the location of the .dll file, the location of which you have noted, left click the file and select "OK"
- then re-tick the "iCloud Outlook Add-in" and "OK"
- re-start Outlook and the Refresh button should reappear
enjoy it. :-)

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Hi,
Based on the description, you have a pst data file in Outlook 2010 and an ost data file in Outlook 2013, I think you are probably using an IMAP account?
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Outlook 2010 is an email client that runs on a PC. It does not run on an iPhone at all.
Is this a corporate email account? What did your IT department say when you went to them about the problem?
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Thanks all.
Was checking to see if the issue Samorren has discovered in the following post might have been in play for you:
iTunes 11.1.4.62 freezes while syncing with Outlook
(Similar issues can hit iTunes and the iCloud machinery, because they both use files from Apple Application Support ... hence the quick check of your situation over here.)

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six of one and half a dozen of the other
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Thank You,
Wøødy

Outlook 2010 additional account same server - mail not sending

Hi,
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Also, I have disabled the new user account in ADUC in the new domain ([email protected]).

Hi Tippers,
Sorry for the late reply.
Yes, you are right. OWA works well but Outlook not, it seems like an issue on the Outlook Client side.
Our emails stuck in Outbox without errors, this problem is likely to be related to our local Outlook configuration.
If Outlook is not sending only some Outbox emails, please make sure we don't have the habit to preview/open/click on Outbox emails.
If Outlook is not sending any of our Outbox emails, please try one of the following methods:
1. Please make sure Outlook is not set to the Offline mode.
2. Run Outlook under safe mode to avoid some AVs, add-ins and firewall.
3. Our Outlook data files may be corrupted. Please performing a data file scan via Outlook ScanPST tool.
More details in the following article:
Outlook is not sending email – stuck in Outbox
PLEASE NOTE:
Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please make sure
that you completely understand the risk before retrieving any suggestions from the above link.
Also suggest re-creating a new thread on Outlook Forum to double confirm this issue.
For your convenience:
http://social.technet.microsoft.com/Forums/office/en-us/home?forum=outlook
Hope it is helpful
Thanks
Mavis
Mavis Huang
TechNet Community Support

Outlook 2010 - Cannot view Plain Text Emails

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Sorry cannot post images or link yet as my account is not verified...
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I appreciate the response and the reference articles. I will look at them.
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MICROSOFT Techs, please respond!!!

Outlook 2010 iCloud Add-In causes emails not to send

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