The time is apon me for a bit of a rant about Windows Mobile, specifically with regards to its approach to networking profiles. I’ve been spoiling for a write up on the topic for a while: ever since the PocketPC days, networking on PDAs with windows O/S has been, at least for this techie, a giant pain in the ass.

It should be noted that most of this gripe is based on experiences with Pocket PC 2003 and its predecessors. WM5 and WM6 are recent additions to the fold for me, and a number of the mentioned issues seem to be, if not solved, at least partially smoothed over.

So far, so far the strongest argument I’ve yet encountered for blowing Windows Mobile away in favor of some flavor of embedded linux is the WM implementation of networking. A real shame because aside from that, WM more or less seems to get it right – decent information management, desktop / remote email sync (when you can get past the networking hurdles), and with third party tools, enough access to the internals to keep a techie happy. Except the networking interface.

Windows mobile networking has generally confused me. As a network admin, I’ve dealt with plenty of odd setups, but Windows Mobile truly does take the cake. After a few hours of mind games you’ll likely be begging for a simple ‘do what your told’ setup as opposed to the ‘second guess you because we know better’ philosophy that WM6 seems to adopt.

I have messed around with these devices for longer than I should admit. Many a time I’ve had everything working – for a while. Then it stops, develops amnesia, stumbles about disoriented. Losing wireless has the device utterly, and inexplicably confused, and too often for happenstance a hard reset will get things going again – with the exact same config.

Indeed, there seems to be a new definition of logic when it comes to how networking should function, and often a setting will seem to have no effect, or the result will be inconsistent. It will work for a while then stop. One application will work fine, but another will not. Changing a seemingly unrelated networking parameter has ramifications: things start working in an unexpected fashion or not at all.

The approach seems to be akin to a puzzle game with a random element as opposed to a tool designed to achieve an outcome. Sometimes it will work, sometimes will not. The same inputs to the black box will not always render the same output.

Now I’ve had a bit of a dubiously qualified rave, making vague accusations and pointing my finger about the place at indistinct phantoms, here are some actual specifics I have encountered.

Most, if not all of the headaches come from the implementation of multiple networking profiles – “My Work”, and “The Internet”. Now this multiple config setup could have been cool, if they hadn’t crippled them both in subtle and painful ways. Setting them up in seemingly logical configs does not work (ie you expect to connect to a network, access that network through a proxy if specified, access it directly if not).

After many many hours of trial and error I found some answers on the net which pretty much confirmed there wasn’t much to be done except half baked workarounds. I’ll outline the situation briefly; Its been a while since I struggled with them properly, but heres the gist:

• Options for the different networking areas are buried, entwined, and otherwise concealed within layers of subterfuge – idiosyncratic ways to get to oddly named tabs and mislabeled options, labels and check boxes. I can only assume this is to prevent joe businessman getting into the settings to mess them up, but they do equally well at confusing IT techs who expect some kind of consistency with other configuration standards. I’ve been hoping since the pocket PC days that they would throw all this out and start again, but sadly WM6 seems to have retained most of it.

• “My Work” traffic is defined by the device as any server accessed without a period-delimited dns entry. Whaa… So ‘ourmailserver’ would be accessed through whatever the ‘My Work” profile uses, but ‘ourmailserver.internaldomain’ won’t be. You don’t get an option to change this. Also, its not specified or appear to be documented anywhere obvious on the device.

• To get to the internet via a connection associated with the ‘My Work’ profile, you must have a proxy server entered. You do not get a choice. No proxy, no internet, regardless of whether you happen to have direct access or not.

• You can specify a list of addresses NOT to use the proxy/internet profile for. (Exceptions). This seemed to be a workaround to get access to the net via VPN from the wireless network on campus (see below).

• Activesyncing the device with a PC seems to arbitrarily replace the proxy settings on the device with the proxy settings of IE from the PC being synched. It took me a while to figure out this is why my old bosses settings would work for a while on his GPRS plan (which uses a proxy server on the ISP’s network), then die (after he docked his pda and the settings were replaced).

• VPN-ing only seemed to be allowed through an ‘internet’ connection. (this might have changed in WM6 – except… well see the next point). In WM5 The device assumes you will never be connecting to a VPN from the ‘My Work’ network. Wrong in our case, as we connect to a VPN internally when using wireless – 99% of how the PDA works. To get this working, the wildcard exceptions workaround needed to be used.

• VPN in WM6 – what VPN? It doesnt work. Sets up fine, then never offers to connect, and attempts to connect manually fail silently. Less than ideal. Fortuantely re-jigging the new devices to use our internal proxy seems to work for most functionality.

• Pocket IE is hardwired to obey the O/S proxy settings. Often I was unable to access web pages because of some internal device proxy confusion based in the proxy settings (third party tools would show clean pings and connections possible to the proxy server and / or the destination server). It is notable that I could often get pocket mozilla (minimo) and pocket opera to load pages when pocket IE would not.

• Pocket MSN seems very sensitive to proxy settings. I have only ever had it working when the device has a direct connection to the net, wither via activesyncing to a PC which has a direct connection, or using GPRS.

Complaining like this smacks of heresay, because its hard to be specific about just where and in what manner things are broken. The place is like a wall of mirrors – and the diatribe sounds like someone ranting on without qualification. It sounds like the ravings of a lunatic, of a n00b, of a crazy man.

In truth, a lot of the complaints I have had seem vapous unless you’ve experienced them yourself. I know – I know these problems exist because I’ve sat for hours struggling with the damn things, and I’ve managed to set up plenty of networking devices before, and they work, so I have to lay it back on the device in question rather than any outstanding incompetence on my part.

I think the problem is this: if you add to the various configuration craziness mentioned before the fact that wireless can be flaky, you have a test environment with shifting terrain which makes it difficult to baseline and describe properly, let alone start mapping out solutions. Regardless, Windows Mobile devices are set to become part of the widespread IT landscape at my workplace very soon, and it will be at least partly up to yours truly to ensure it happens as smoothly as possible, so a-testing I must go.

UPDATE: I have posted a few solutions to some of these issues in the post Windows Mobile 5/6 Networking Profiles, Proxy and VPN setup.