Problem with Outlook 2013 messages stuck in outbox

We are using IMAP with Outlook 2013. Outlook 2010 users are not having this problem.

I have a couple of users, one in particular (the Big Boss, unfortunately) whose messages too frequently get stuck in the outbox. The error is 0x80040201:
Outlook error 0x80040201The stuck messages have some odd characteristics. For example, the 2nd stuck message shows a size of 0, even though it contains the same 3 spreadsheet and 1 PPT attachments as the 1st message. The 1st two stuck messages shown are to the user himself. (see image)

The user is able to get his messages out by copy/pasting pieces of the message body into a new message. Then it sends OK.

I've searched quite a bit on this including the typically very good website Most sites, including this one, recommend deleting and recreating the profile, which I've done several times.

This site:, "Solution two" indicates that there might be a problem using email addresses that were formerly in Exchange but are now used with POP (or IMAP). It recommends
change recipient properties and set EMAIL TYPE to SMTP, and EMAIL ADDRESS to something like "" and do not use auto-substitution of recipient, or DELETE cache record in pop-down list by pressing UP, DOWN and DELETE button on keyboard and then typing email again...
Not sure what he means by the whole phrase starting with "do not use auto-substitution of recipient", but I did locate the address book field 'Send From' which shows EXCHANGE ADMINISTRATIVE GROUP (see image). As one experiment, how would I edit this field?

Otherwise, does anyone have any idea what causes this and how I can fix it?
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jmarkfoley --
The Outlook profile could be corrupt
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Karen FalandaysTraining SpecialistCommented:
Hi jmarkfoley,
See if the issue is now resolved. I think there must have been a few SPs in the past week that messed with the profiles, as I was having the same issue and it went away with no intervention
MarkAuthor Commented:
OK, I did create a new profile for this user. Not 100% sure that fixed the "stuck in outbox" problem, I have a message to the user to let me know. kfalandays, maybe it would have likewise gone away by itself.

But I'm having bigger issues. Perhaps this should be another post ...

Another reason I created a new profile for this user was because his WebDAV calendar stopped getting updated. After creating the new profile he was able to re-publish his calendar. About a week later - same thing, no calendar updates. This time I did not have to create a new profile. His Outlook had the 'Publish to WebDAV' server option enabled -- as if the calendar had never been published, or rather, become unpublished. I did the 'Publish' and is calendar is now updating to the various people he subsequently invited.

Meanwhile, a few days ago, The Boss asked several of the other staff to publish their calendars to him. 2 have Outlook 2010; 2 have Outlook 2013. The 2010 users published, no problem. The 2013 users show the 'Publish to WebDAV server' option, but when clicked absolutely nothing happens. No error message, no options dialog, nothing. The Boss also has Outlook 2013 and was able to publish his calendar, but as described this seems flakey.

So, is there something fundamentally broken with Outlook 2013/IMAP? We've had these problem and more with add-ins, sending email from Excel, Foxit, etc. Meanwhile, Outlook 2010 seem to work fine -- I'm not constantly re-creating profiles and no one ever loses their shared calendars, nor do they have to periodically republish calendars. I am sisyphus-ing the proverbial rock up a hill with this product? Are others having these kinds of problems or is it just me. I'm seriously considering downgrading to 2010.
MarkAuthor Commented:
OK, I did create a new post:

I'm splitting the points between you because both suggestions are probably correct, but neither really solve the problem.  jcimarron, I've created new profiles several times which does solve the problem, for some period of days, then I'm back to having the problem. So, that's not an acceptable long term solution. kfalandays, maybe the 'updates' contributed to the problem, but no real way to be sure in the short term. If it never happens again, the maybe.
Thanks for telling us the outcome.
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