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iPhone Mail & Proxy Servers

At work, I'm fortunate enough to be able to access our wireless network. I have the connection configured to use a proxy server which is required for all traffic passing through our firewall. The iPhone web browser works just fine access pages with no problems at all.

However, the Mail application is unable to reach my mail server (I use .Mac). I can get to the server just fine using the iPhone web browser so I know the connection is working and the server is responding; however, attempting to access it with the mail application results in the error message, "The connection to the server 'mail.mac.com' failed."

I'm guessing this is because the Mail application is trying to access the server directly, but it actually needs to route the connection through my proxy server. Is there some way to configure the Mail application to make this work?

MacBook Pro 17-inch, Mac OS X (10.5.3), Safari 3.1.1

Posted on Jun 10, 2008 8:18 AM

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16 replies

Jul 29, 2008 10:41 AM in response to alice_anto

I haven't been able to figure out any way of getting it to work. I did notice that with the 2.0 firmware, the iPhone is able to connect to Wi-Fi networks that utilize PEAP authentication. That's at least an improvement on past abilities and makes it possible to connect to my corporate WLAN without too much difficulty.

I'm not prompted for my username/password instead of the WLAN password like you normally find on WEP and WAP encrypted networks. Typing in my credentials results in a connection.

Now, if I could just figure out how to get access to the MAIL client, I'd be a happy camper since the AT&T signal in my workplace is pure crap.

Aug 14, 2008 8:51 AM in response to thunderwalker

Not so far. It seems that Weather, Stock, and a vast variety of iPhone Applications from the AppStore work just fine utilizing the proxy settings established with the connection parameters and settings, but for whatever reason the Mail application doesn't.

The only thing that I can think of is that it is trying to directly establish the connection on an outgoing SMTP port (port 25) instead of routing it first through the proxy server. Any corporate environment I've ever worked in doesn't allow direct connections to port 25. You have to first route the traffic to port 80 (or whatever port the proxy server is configured with) and then direct the traffic to port 25 on the destination server from that point on.

I too would love to see this resolved in a future update, but I'm not sure how Apple would do it.

Sep 28, 2008 10:33 AM in response to Dwimmerlaik

i have the same problem my proxy firewall doesnt allow apps on my macbook like mail and entourage...also my ipod touch doesnt work with apps like stocks, weather, and youtube however when i went to the apple store and used youtube and went back home to try it it can only load the videos but cant refresh the featured videos and stuff
it recently works with the itunes store on the ipod touch on the new 2.1 firmware but everything else like the aim app from the app store and myspace or any other app that uses the internet doesnt work

Jan 5, 2009 1:21 PM in response to EuroPWM

Sorry, I have no solution, but I'd just like to add my voice to the general clamour (hoping that Apple might do something about it). I have an HTTP proxy at work (squid, using port 8080) and wifi. I observe the same behaviour, most notably the BBC iPlayer will not work and neither will FStream. The iPlayer works fine on my Macbook (using the same wifi network and proxy settings) so not sure why the iPhone cannot get it together.

iPhone Mail & Proxy Servers

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