Gmail now supports it.
About frickin’ time. Gmail is awesome, and we’ve transitioned here at work from mostly Outlook Express to Google for Your Domain. This makes a lot of administrative stuff a lot easier for me, especially backups. But Gmail still has a few things I wish could be tweaked, and for a long time efficiently adding multiple attachments was one of them.
Most weeks I have two or three emails that require me to send a dozen PDFs to one of my bosses. I know that the correct answer is “just use zip files” but one doesn’t do that after the boss complains the first time.
For a few months I’d been using the gAttach Windows app to let me add as many files to a draft as I like directly from the Windows shell, but that was a kludge and the app stopped working about 6 weeks ago. I’ve been clicking three times for every attachment. Madness.
Now, all I have to do is click “browse”, drag-select the files I want to go, and click OK. Done.
Kudos, Google. Now let me attach .exe files to my emails!