Jeffrey, its apparent that this issue has yet to be resolved, and is unique to Outlook (hotmail) on Android devices in the 4.0+ iterations of the android operating system. Why not simply acknowledge the problem exists and offer immediate, though not
ideal relief? Refer to the reader who posted a solution that, at least, gets Outlook users out of the dead end situation when they find multiple important "sent" emails stuck in their outbox? That solution is to simply delete the oldest of the emails stuck
in the outbox while a verifiable wi-fi connection exists, and all the following outbox bound emails are instantly released and sent to their intended recipient. Not a perfect solution, but at least it resolves the immediate problem we hotmail clients suffer,
without apparent, viable options to release their "imprisoned", but important messages. When Microsoft help reps start pointing fingers at improper settings or corrupted apps, who benefits? Then acknowledge the fact that this isn't a user initiated
mistake, so people that have chosen to use Outlook don't have to come searching for help that may or may not be found. Sidestepping the existence of software compatibility or design shortcoming brings this conclusion to mind: if you aren't part of the
solution, you are part of the problem.