Let's say you've connected one or more SharePoint document libraries to your Outlook, perhaps using these well-written directions from the MS Office Outlook Team Blog. While offline, you edit several of the documents in one of your synched document libraries via the folder pane in your Outlook. When you connect to the network again, you want to update the live document library with your changes.
You might expect there to be a means of batch updating the documents, perhaps by right-clicking the document library name in the Outlook folder pane, or by hitting the Send/Receive button. But in fact you need to open each changed document in order to prompt the update.
That's clunky, but clunkier is the message box you get to perform the update:
If you click the Update button, the server is updated, the message box goes away and the document remains open (no feedback for "successful update"). When you attempt to close the file, the same message box appears. You need to click "Do not update server" in order to be able to close the file.
Why make the message appear twice in order for me to be able to get out of my document? How about an "Update and close" button? If I have to do this for every document I've edited while offline, the amount of time it takes to update, try to close the file, and click the "do not update" button will become significant.