As if to emphasize my paranoia about plugins, yesterday I got a call from a client who has successfully used the YouSendIt Outlook plugin for months. It stopped working for no particular reason; when she pushed “Send” on a message with an oversized attachment, YouSendIt’s dialog box would pop up and the message would be moved to YouSendIt’s special Outbox folder, where it would sit, immobile, doing nothing. YouSendIt’s progress bar showed that nothing was happening. A couple of times it taunted her by showing that 0.3% of the file had been uploaded before it went back to sleep.

I got on and did the usual troubleshooting: restart the computer; remove the plugin and reinstall it; run Outlook offline, then back online; remove the pending messages and start a new message; remove the plugin, upgrade to Outlook 2007, and reinstall the plugin; move slowly to be sure the hosted Exchange server was finished syncing at all times; light candles at the corners of a pentagram chalked around the computer and invoke the Elder Gods; use colorful language and interesting expletives; etc. Nothing made any difference. The attachments just wouldn’t go to YouSendIt.

Nothing had changed on her computer. The YouSendIt plugin had worked the day before, and probably works today for thousands of satisfied users. It wouldn’t surprise me if it starts working again for my client, again for no particular reason. This shouldn’t dissuade you from trying it if it meets your needs. Instead, it’s just one more cautionary tale that sometimes things just won’t work.