Configuring the iPhone and your environment for wireless corporate email

Question

I'm posting this as a top level thread, because I'm certain that there are others out there, who like me, are trying to figure this out.
Configuring the iPhone for Enterprise Use
With Apple’s release of the iPhone, IT organizations are presented with an interesting challenge. Senior execs, gadget heads, and technoratti are all flocking to this device, heralded as the be all and end all of smartphone telecommunications technology. As these devices begin to flood into our organizations, we are met with the challenge to ‘make it work’.
After much explaining that the iPhone is not intended for Enterprise integration, and many discussions surrounding the technical feasibility of bringing said devices into the fold, and being the resident Mac and Linux head with an iPhone in hand, I decided to embark on the mission of making one ‘work’. I succeeded in part, however it’s not the kind of ‘work’ that is going to be viable for most end users.
First of all, it’s important to understand that the email client for the iPhone is a modified version of Mac’s Mail program. Not the best client in the world, but it does support Exchange integration. It also does external email sources, such as Yahoo and gMail, very well. For my interest though, I’m focusing on the Exchange integration functionality, as that is just about everyone’s corporate standard.
Bringing this task to fruition requires some understanding about the limitations of the iPhone, as well as some of its current quirks. Wireless802.11x, EDGE, VPN and Mail are all components necessary to provide a serviceable solution for mobile email access, and each of these things has some peculiarities that don’t appear to be fully worked out by Apple at this time.
For instance, within my organization, we have a secured wireless connectivity option available within our building; however, the SSID of this network is not broadcast, for the obvious reasons. SO, connecting the iPhone to it is a manual process of defining the network, and automatic reconnection seems to be very hit or miss, so it becomes far less of an option for any form of direct network access to your Exchange environment. (As an example, I had to redefine that network, on the iPhone, at least half a dozen times during this process.)
The other components have equally quirky issues, and I will discuss the how’s to get around them below.
In coordinating this into a cohesive plan however, I will break this into three sections;
1. Wireless and EDGE connectivity
2. VPN access to your network
3. Connecting to Exchange
So, without further ado;
Wireless and EDGE Connectivity
The wireless capabilities of the iPhone are, on the surface at least, excellent. It connects seamlessly to unsecured networks, offers the option of prompted or unprompted automatic connectivity, and is capable of 802.11G performance. Not bad for such a small package. However, it is very limited in the forms of secure network access it supports. These are, to quote Apple’s website; (and my iPhone)
WEP Password
WEP hex or ASCII
WPA (personal)
WPA2 (personal)
Now, due to the obvious security problems in implementing WEP security, it’s likely that any network you run into is going to be WPA or WPA2. The iPhone ONLY supports the personal versions of these protocols, so be aware of this going into the situation. If you’re not connecting to your work or school wireless, and you’re entering the information correctly, then it’s probably because they have the Enterprise version of one of the protocols enabled. If that is the case, then you’re either hunting for unsecured hotspots, or else depending on EDGE.
In my case, I did have access to a WPA2 (Personal) enabled wireless signal to connect to my internal network. I thought my problem was half solved! I defined the connection, the wireless capability of the phone worked perfectly, and I was connected. I was wrong. Apparently, and judging from the Mac forums I’m not alone in this, the iPhone does not do a very good job of RE-connecting to a secured wireless network. It does an even worse job, when this is coupled with the fact that it doesn’t do a very good job reconnecting to a wireless network with an unpublished SSID.
After much fiddling and research into this, I determined that this simply was not the way to go, and I abandoned the idea. I wasn’t about to compromise my network security in order to get this silly phone working! So, that left me with either unsecured WiFi, or EDGE.
Either one of these connects pretty seamlessly, and gives me a relatively decent Internet connection. There are some issues being reported of the iPhone swapping between EDGE and WiFi for not apparent reason, but that said, it can still be made to work.
Now that I had this connection outside of my network, I obviously had to consider options for getting a secured connection into my network, which of course leads us to;
VPN Access Into Your Network
Being that this device was touted as the ‘real internet’ I was very excited to see if I could achieve this connection through my SSL VPN appliance. To make a long story short, I could not. Because Apple’s idea of the ‘Real Internet’ apparently does not include those wacky concepts like Java support, this proved to be impossible. My Apple cohorts will scream that it does support JavaScript, but we all know that that and 2 bucks will get you a small coffee at Starbucks… and not much more.
(The iPhone also does not support Flash, but that’s a topic for another conversation. I know, how could they leave that out? I’m amazed too, but then Steve Jobs always has been a bit too arrogant for his own good… I mean what does he expect, we’re all going to rewrite everything into QuickTime??? Please.)
Since that option didn’t work, I was left with the wide selection of two possibilities provided within the iPhone software. Either, a PPTP or L2TP VPN tunnel.
We went ahead and configured a PPTP connection on one of our Cisco routers in order to test this. It didn’t work. I couldn’t connect to it. Tried and tried. Nada. SOOOO, we said OK, and configured a L2TP connection on one of our Cisco routers, with similar results.
Figuring that this was something in the config, we called Cisco, and did the technical support dance with them for several days, trying one thing after another to get this connection to actually work. Nothing helped, and it never worked using either protocol. Then, I noticed an obscure article somewhere on some website that said something to the effect that getting one of these tunnels to work from the iPhone to Cisco was nigh on impossible.
About the same time, my senior network guy said screw it, let’s put this on a Microsoft server. And so we did. Now, this is interesting in it’s own right, because configuring out of the box L2TP or PPTP on a Microsoft server results in a default authentication method of Windows Authentication. This does not work for the iPhone, because it has no idea what to do with the Windows security token it receives. So, you authenticate, and then are immediately dropped due to an inability to communicate with the PPP server.
Fortunately, we (as do most organizations) have a Radius server. We selected Radius authentication, configured both sides of the Radius authentication setup properly, and launched the PPTP tunnel…. AND…. EUREKA!!! The iPhone’s VPN software connected, authenticated, got an IP, and I was on the network! Well, no.
After about 2 seconds, I realized that while I did indeed have a connection, I couldn’t do anything with it. Couldn’t even browse to an internal site via IP address. The connection was up, the connection was working, the connection was useless.
So, we decided to give L2TP a shot. Configured it pretty much identically to the PPTP setup, used Radius, launched the iPhone client, and finally, after many days of screwing around, it worked. Now all I needed was to get my email working, so I started working on;
Connecting to Exchange
In the Mail program on the iPhone, the first time you launch it, you’re presented with the ability to configure an email source. However on subsequent or additional accounts, you must go under Settings, Mail to get to this functionality.
Going into the Mail configuration, I selected an additional account, the account type is, of course, Exchange. The configuration components are pretty obvious, however some things of note are;
Do NOT include your domain information in the User Name field
For all Host Names, use the fully qualified domain name of the server, or else IP
You WILL need to have SMTP enabled somewhere in order to send email
Anyway, I set all this up, and nothing happened. It said that my server was not responding. Did a little research, and it turns out that the only way to connect to Exchange is through an IMAP4 connection, and just in case you didn’t know, IMAP4 is disabled by default, so you have to enable and configure it.
Went onto the Exchange server, set the service to Auto, Started the listener, and finally, at long last, EUREKA! I finally had Corporate email on my iPhone, connecting securely, and not sending anything plain text anywhere. Hooray!
Now for the problems with this solution;
First of all, it depends upon VPN access into your environment, something that you may or may not be comfortable with. One good thing is that the iPhone does prompt for password to reconnect, and will tie the continuity of the VPN connection into the general phone lock security, such that an inability to provide the appropriate access code to a locked phone results in the VPN not being accessible.
The VPN of course is dependant upon a reliable network connection. I’ve noticed that it’s somewhat graceful in switching between WiFi and EDGE, however it’s not totally graceful, and you can experience some hinky things, like being able to send and not receive, or the mail client saying ‘Connecting’ for about 5 minutes before it figures things out.
The best cure for this is to simply stop and restart the VPN connection. Note that when you reconnect, the first attempt will prompt you for a numeric password, this is meaningless unless you have the device lock turned on. Just enter anything. (I think this is another bug) THEN it will re-prompt you for your real VPN password.
This solution for email delivery is obviously dependant upon the VPN connection being active. I’ve noticed that at times the iPhone will disconnect the VPN (probably when service switching) and not bother to mention it. When that happens, of course the VPN must be restarted.
For the lazy, this is an inconvenient solution because while it would appear that the iPhone will cache the VPN password, in fact it will not. That means that each re-launch requires that you re-enter your password. Not terrible for me, but I could see it being very tedious for the average corporate user.
The OSX Mail client has several little deficiencies, which may or may not impact your use of the device in this manner. For instance, if you have subfolders defined for your inbox, and server side rules to move mail into them, then you will not see any synchronization of that mail until you actually select the subfolder. Also, since there is such poor management of attachments and downloads, moving anything around via email on this device is nigh on impossible.
EDGE access to your corporate email, via a VPN, is a bit sloooooow. It works, it’s certainly fast enough for my purposes, but it’s not the slick quick access that we’ve all become accustomed to with Blackberry and Good devices. The lack of 3G support becomes a very noticeable shortcoming here.
(Why Apply didn’t simply partner with Good Technologies to crank out a client for this thing, I’ll never understand, but I guess you can refer to my comment above about certain people’s arrogance.)
The biggest problem of all of course is that it’s simply klugey. I hate klugey. But, with the capabilities at this device’s disposal, and given Apple’s ambitious, if a bit idiotic, stance that no third party will develop software for the iPhone, then this is about as good as it’s going to get for now.
It is my understanding that overseas there is some initiative underway to provide a more seamless Visto or Synchronica integration for enterprise email. However, given Apple’s unbelievably restrictive agreement with ATT regarding this device and the OTA necessity of delivering the client, I seriously doubt if we’ll see this in the near future in the US.
But I digress, so…
In Conclusion
This solution is not for the faint of heart, it doesn’t work all that well, and it has way too many moving parts that are subject to failure. However, I would say that this solution is serviceable for the corporate technology professional who needs email, and really, REALLY wants the other features of the iPhone. (ie, phone whores such as me.) It requires patience, it requires an understanding that this is not a 100% thing, and there definitely needs to be a prebuilt expectation that this device will not serve your email in anything approaching the manner to which you’ve become accustomed.
As long as all of that is okay though, then go right ahead, set it up, and enjoy!
The Short Version;
(I put this at the end because I want everyone to feel my pain!)
Wireless:
Use unsecured wireless or EDGE. Secured wireless may be serviceable as long as the SSID is broadcast, but there are known issues with this.
VPN:
L2TP, shared secret, running on Microsoft server, with Radius. (May work elsewhere, but doesn’t seem to run on Cisco at all) Accounts enabled for external access.
Exchange:
Configure IMAP4 Virtual Server on your Exchange environment, ensure that you have some SMTP resource for outbound email, use fully qualified domain names for all servers (or IP) in the mail config and do not include any domain prefix or suffix for user accounts.
The BIG Disclaimer at the End
Please note that all of this is provided ‘as is’. It worked for me, and I hope it works for you. To my knowledge, it’s not endorsed by Apple, and I’m not in the business of providing support for this thing. If it breaks something, if it doesn’t work, or if you simply don’t like it or me, I don’t care. However, if you have a question, and I’m not busy, and I feel like answering, I may lend a hand. You can email me at
Matthew dot Yotko at mac dot com
Don’t be surprised or offended if I don’t answer. Also, understand that I don’t check this address every day… Maybe a couple times a week.
Macbook Pro   Mac OS X (10.4.10)   iphone

Answer 1

Thanks, now I understand why the wifi keeps dropping. On my personal wireless network, it also seems the distance from the access point is not good compared to my laptop. At work our network & exchange teams don't seem to have the desire to struggle with this "toy" until customers start forcing its adoption. I am using OWA and it works fine over EDGE. I will share your posting with them.
Thank you again.
Dell   Windows XP Pro