Dropbox and WPAD auto proxy detection

dropbox-1We recently changed our proxy configuration method from manual settings to auto detect to fix some issues we were having with an Outlook bug affecting Office 365 Autodiscover, unfortunately around the same time Dropbox seemed to stop working.

After doing some testing I found that I could do either of the following to get it to work using version 2.6.2 from the Dropbox website:

  1. Set proxy manually in Windows, Dropbox set to auto
  2. Leave proxy as auto detect in Windows, set Dropbox manually

In the latter situation a valid login has to be made after the proxy configuration otherwise Dropbox will reset itself back to default (auto) settings and any further logons will fail.

A bit of research led me to the Dropbox forums where it turns out there’s another build available with new features that haven’t yet made it to the stable branch. Version 2.7.38 contains WPAD support. The Dropbox staff on there are helpful and replied quickly which is always good to see if you have any other queries.

I downloaded the slightly updated version 2.7.39 and deployed it via ZENWorks using the /S switch to make the installation (mostly) silent. Users still have to accept a UAC prompt which is a pain but can’t be helped. Logging in with the updated version brings up a login screen straight away with Windows and Dropbox proxy set to auto and we’re away 🙂

We also add an explicit entry in our WPAD file to ensure Dropbox goes via the proxy, it might not be absolutely necessary but removes all doubt about where the traffic is going which can never be a bad thing (replace X.X.X.X with your proxy server IP address)

/* Exclude Dropbox from proxy here */
	if (shExpMatch(url, "*dropbox.com*"))
	{ return "PROXY X.X.X.X:8080";}
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