Emails stuck in outbox at random - Exchange 2013/Outlook 2010

This one particular user is set up slightly differently to everyone else. Shes a PA to the CEO - call her A.

She logs in to the network as A and has her own mailbox. However, she full access to CEO mailbox and user B.
Her outlook is set up as default CEO, with A and B also. She rarely uses her own A mailbox.

Most of the day she SENDS AS CEO.

Intermittently, emails get stuck and remain in the outbox. Sometimes if you go into email and send again it works (but leaves copy behind in outbox). Sometimes not.

Also, new emails SEND AS CEO go into CEO SENT items. Emails replied to (even though SEND AS CEO) go into user A SENT items.

Tried new profile. Still the same.
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paulfoelAsked:
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Venn TorrenceCommented:
Some Outlook common reasons of email stuck in the outbox of Outlook, some reasons are - authentication  problem, offline mode set, no default a/c is set, Outgoing emails scanned by anti-virus etc. You need to check manually to find the cause of this error – you can visit here to detail description and solution of this error: http://www.msgconverter.net/blog/outlook-message-stuck-in-outbox
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Ibrahim BennaTechnology LeadCommented:
Are you using Cached exchange mode? If so try to disable it and see if it works. Or at least try to select not to cached shared folders in cached mode.
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paulfoelAuthor Commented:
Online mode only.
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Ibrahim BennaTechnology LeadCommented:
Her outlook is set up as default CEO, with A and B also. She rarely uses her own A mailbox.

Have you ever considered configuring Outlook with the CEO's profile for this user so that she logs into the computer as herself and then logs into Outlook as the CEO - seeing that she rarely uses her own mailbox?
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