Recently I found myself out of the office with web mail access only. As we have Exchange 2007 I was able to connect to our web mail via Outlook Web Access (OWA). I found that I would compose a new email (or reply) and hit 'send', but the new message would only be persisted and get stuck in the Drafts folder.
This seemed to only happen on occasional days, and it didn't matter if I was using the OWA Light Version or Full Version. Nor did it matter that I was using it from my mobile or laptop or home computer.
After some hunting I found the solution:
Don't leave Outlook running under your session/user account on any other computer! Close all other sessions you may have open!
It appears that if you have an active Outlook session from say a desktop, or remote desktop (TS) connection - your web mail from OWA will not send. This was a hair pulling event for me - hopefully it helps you with a possible frustrating set of patches, updates, security changes in your browser etc. etc.
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