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iOS 5/iPad 2 proxy settings not being remembered

I recently upgraded one of my iPad 2's to iOS 5, but I seem to be having an issue the Wi-Fi connection in work. The wireless network has a hidden SSID and it requires some Manual proxy settings being put into the wireless config.


When I input the relevant information it seems to hold fine for a few seconds but when I go into Safari it prompts for an https:// proxy username and password, if I input the correct details it just prompts again and no matter how many times I input the correct information it still prompts for it over and over again, to the point that you just have to switch the wireless off to stop the message from flashing up.


I have an iPad 2 on iOS 4.3.5 and the same setting work perfectly fine on this iPad 2 but will not work on iOS 5.


I have even tried a Linksys Wireless Access Point plugged into the network with no hidden SSID etc and I still get the same thing on the iOS 5 iPad 2 it continually prompts for the proxy details, but the iOS 4.3.5 iPad2 works fine.


Is this a known glitch or am I just being a total idiot : ( ?

iPad 2, iOS 5

Posted on Nov 2, 2011 6:15 AM

Reply
83 replies

Jan 24, 2012 5:38 AM in response to Gibbopool2011

Hi Ladies/Gents,


Am happy to say I got a fix that works until Apple releases a solution. Here is a solution if your network uses ISA Proxy server's NTLM authentication(i.e.,Microsoft ISA)


Download the CNTLM 0.9.9.0.1 & Python language interpreter version 1.5.2 or higher and install them on the central location(in my case I used the DC), create one account on AD that has full access to the Internet and allow it on the ISA Proxy. Define the account on the cntlm.ini file and on the iPad proxy authentication user details and Bob is your uncle.


Please follow these links for more info.

http://ntlmaps.sourceforge.net/

http://cntlm.sourceforge.net/


Hope it works for all of you guys, cause no more annoying proxy authentication prompt for my users!!

Jan 24, 2012 7:23 AM in response to Javisto

That, is NOT a fix. That will also allow every single person on your site to access the internet as a single user... bypassing any security and accountability the company needs to uphold. As I work in education, that would be a HUGE "duty of care" issue. I'd get a repremand for even suggesting it.


I HAVE tried similar work-arounds as a proof of concept, and found the best and easiest is "Authoxy". With that I can set up my Mac as the Proxy server, configure it with my user credentials, and then set the iDevice proxy to use my Macs IP address and port for access. In this scenario, I also created a DHCP reservation for the iDevice to ensure it had a single, known IP address, and then configured the firewall to ONLY allow that specific host for remote access. Authoxy worked perfectly for the iDevice AND for various Flash/Java/Plugin/App authentication issues on both Snow Leopard and Lion. It is NOT a solution I would recommend anyone perform though. If you're in corporate IT and do this, you're a fool. If you're not in IT... I expect you to be fired.


NOTE 1: I didn't reply before with a PAC file, as my initial trial success could not be replicated on other devices and I still got the prompts.


NOTE 2: The only decent solution i have found, for those with ISA/TMG (and probably similar in other firewall/proxy packages) is to enroll ALL your iDevices in a DHCP pool as reservations. Then assign that IP range in ISA a new "Computer" rule and set it as unauthenticated. Get your users to supply their own credentials for the initial wireless access. This, unlike the solution above, means that all iDevice access can still be monitored and filtered (if you use filtering) via IP address assignment (which is listed against a user in our DHCP description). Filtering may not show "Joe Bloggs", but does show "172.16.15.96" which has a DHCP description of "Joe Bloggs". We have this running right now as a work-around.

Jan 24, 2012 11:04 AM in response to Gibbopool2011

NKX point taken hence I quote "until Apple releases a solution" what is important at this stage is that users are able to browse without getting annoying prompts and that gives me enough time to fine tune the fix or get another way of sorting out the problem.


In my scenario the only people that are allowed to use iPad in the company network are executives & directors, they're individual accounts are setup for full internet access anyway which doesn't really make any difference and am the only person that knows the account.


These another option if you have individuals with different internet permission on your ISA server, which is a administration nightmare. On the cntlm.ini file you can specifiy all the users accounts that use iPads and authenticate on the proxy using those accounts instant of one generic account like in my case, that also works as I have tested it.


Please note if this fix or work around is not suitable for your environmet don't implement. But thanks for your feedback.

Feb 14, 2012 10:34 AM in response to Gibbopool2011

I am a sysadmin for my work. I am having this same problem using an IPCop authenticated proxy with iOS 5 devices.


I think I have fixed it temporarily (until Apple get their arse in gear) by using the following PAC file stolen from Wikipedia. I have served this from my Mac using the build in Web Sharing, however I imagine any sort of LAMP server or equivalent would work as well.


function FindProxyForURL(url, host)

{

return "PROXY 192.168.1.1:3128; DIRECT";

}

Mar 1, 2012 8:01 AM in response to Gibbopool2011

I take it there are no new developments on this? I work in an educational environment and as a previous person said the web access has to be extremely controlled so my IT dept are unwilling to use any of the work arounds suggested previously. This isn't good as I just deployed a large number of iOS devices in my facilities management dept which are basically unusable and may as well be used as expensive door stops!


Come on apple get your act in gear and sort this out or your going to loose many of your corporate customers.

iOS 5/iPad 2 proxy settings not being remembered

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